October 31, 2022 • 38 mins
It finally happened! Dean is back from his exotic proposal to Caelynn and he’s ready to share all the magic, all the tears, and every intimate detail of how he popped the question!
See omnystudio.com/listener for privacy information.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hell I Suck At Dating with Dean Anglert and Dared
Haven and I heard radio podcast. Hey, welcome to a
very very very special episode of Help I Suck At Dating.
(00:23):
We've been doing this podcast for quite some time now,
and throughout that time, uh, you have seen both Dean
and myself be single. You have seen us both being
committed relationships from paradise. You have seen me get engaged
married and have our wonderful little boy, Dawson. And now
(00:47):
on this episode today, October two thousand and twenty two,
whatever episode it is of Help I Second Dating, we
can say that Dean Angler Deanie Babies is engaged to
Kaylin Miller. Keys. Have a round of applause, ladies and gentlemen. Yeah, Dean,
(01:08):
how you doing, buddy? Congratulations? Well, first off, Jared, you
look twenty years younger right now because I shaved. I
don't think i've seen your cheek or your jaw bones
in five years. I mean it's been at least that long.
So we did Batman for Halloween, so I had to
shave down really show off the jaw. You know, I
gotta gotta get myself into that Robert Pattinson mode. But
(01:30):
this is not about me. It's not about me shaving
or looking young or tired or dead on the inside.
This is about you. Uh, dean, dude. Congratulations, man, it's awesome.
You're engaged. Dude, you're engaged your fiance. Yeah, I know,
we're engaged. It doesn't feel any different though, to be
(01:51):
honest with you, because I've already worn the wedding ring
for three years, we have already owned a house together
for two years. But don't get me wrong, it is beautiful.
I am very happy be engaged. Um. I know there's
always been a lot of like questions about whether we
just secretly eloped and got married to each other, And
so that's kind of why it's like, while I do
(02:12):
feel different and happy and excited, it doesn't I don't know,
it doesn't. It doesn't if it doesn't feel like there
was like it wasn't as big of a step as
like a normal relationship would have taken. Because we've already
taken that big step. I feel like, you know, So
my first question to you is did you actually lose
the ring or was that a whole lie that you had.
(02:34):
I saw people like commenting that I I have lost it.
If I have lost the ring. I am going to
find it. Uh. It's funny because I asked Kalin with
I got like a cute little half carrot diamond and
like like not in an emerald cut because I don't
think you can make an emerald cut ring that's small.
And ask Kalin and it's like holding the ring up
(02:58):
and she like leaned over and put her hands on
her knees and like looking at it. And I wasn't
sure if she was looking at it because she wanted
to see if it was like the ring that I
claimed to have lost, or if she was just sizing
it up or whatever. And I like felt kind of insecure,
like she was like staring at it um and then
sure enough it was just she was like taking off
her ring that she was wearing so I could put
that ring on her. But then she was like, let's
(03:19):
take pictures of it, like we were like the beach
at sunset, and I was like, I don't want to
take pictures of this ring because I'm embarrassed by how
small it is. It don't be embarrassing. I mean you
should be embarrassed you lost the ring, not by the
size of the new ring. Yeah, well I am I
am embarrassed by both things. And the new ring is
cool too. I was like talking to the guy about
it from He was like, yeah, once you find the
old ring, you can just bring this one back and
(03:40):
we'll turn into like a necklace or something. So I've
decided if I find the new the old ring, then
I'll get the new ring made into a necklace for me. Obviously,
would you wear it as that'd be kind of cute
if you wore it as a necklace. Yeah. And then
I was thinking too, instead of getting her an engagement ring,
I wanted to get her an engagement necklace. That way
we didn't have to trans any diamond at all. But
(04:01):
then I was like, no, that's a little too abstract.
I'm gonna stick with the ring. I'm gonna keep it
a little traditional. I guess what you could do is
you could turn the ring that you actually proposed with
into a necklace, like you said, and have it be
like a family heirloom. So if you guys decided to
have kids, you could pass that down and say this
is the actual diamond that I proposed to your mother with,
(04:22):
and then this is the one that I lost, and
this is the one that I lost the big gass
one is the one that I lost. So she wears
the mom wears that one. Yeah, Mom, because she's not
gonna lose that one. Um. Yeah. So that was how
that all went. I um uh, it was a fun hike.
I want to get Kalin on here at something. Yeah,
I want Kalin on here too. My question is, do
(04:42):
you for you did an eleven mile hike? Did you
do that on purpose because you really wanted her just
to be It's the most deean thing to have her
be completely exhausted, sweaty, tired, annoyed at you, And then
that's when you just turned it all around and propose.
I figured I've tested her so much, there had to
have been one final test for her. So she survives,
(05:03):
she gets the ring, and she passed. She passed the
test barely, though there were times. There were time I
don't want to have her on this podcast episode, but
I do want to have her on at some point
in the future and have her like recount her experience
because my experience and her experience are gonna be very different.
We So it's eleven miles and the weather was perfect,
(05:24):
it was beautiful, sunny, well, it was twenty two miles.
I guess she's because it's eleven miles in and eleven
miles out, and so there's like a halfway point that
you can hike too, so it's six miles in in camp,
and then you finished the next five miles the next day.
And so the first day we get it, we kind
of start late because we had a couple of things
(05:45):
to do in the morning, and then we start hiking
and then we get to the halfway point and we're like, wow,
that was a tough day, but we're here. Let's cook
some food. I cooked us up some sausages and some vegetables.
It was delicious. And then we woke up the next
day and started the next part of the trek. And
that part is like the infamous part of the trek.
It's called Crawler's Ledge. It's like a mile long track
(06:08):
of like sheer cliff on one side. And I I
personally thought it was fine. I didn't have an issue
with it. I want to I can't stress that enough.
I didn't have an issue with it. Um Kalin, on
the other hand, the other party did have an issue
with it. Yes. Kalin on the other hand, was very
(06:30):
angry at me for taking her there. She asked if
we could turn around fifty five times, and eventually I
just started saying, yeah, let's turn around. If you want
to turn around, let's turn around. And but she didn't.
I mean credit to her, because she was crying, she
was angry, she was cursing at me, but she stuck
(06:51):
with it and she eventually finished it. Um, so yeah,
it was. It was a it was a trying experience.
It's I was thinking, too, it's pretty funny, um to
make the person that you're gonna ask to marry you
cry on the day that you're going to propose to them.
Cried for like a like an hour that day. You
want to make them cry, but you don't want to
(07:11):
make them cry out of pain and sheer sadness. You know,
it's supposed to be happy tears that day, right. And
I did everything too. I like, I moved all of
her stuff into my backpack so she didn't need to
wear a backpack. I walked ahead a mile, put my
backpack down, came back with no backpack. That way I
could like like spot her as she moved along the cliffs.
(07:32):
I was doing everything. I was working over time. I
was trying to encourage her as best I can. But
it wasn't I mean, it was scary. They were scary
points I could see, like I could see someone getting
scared in those points, in those moments when you would
say it was scary, Do you think it was scary
because they she could have died. Yeah, she could have died.
Oh my god, you're an insane man. People die on
(07:55):
this hike like semi regularly. Um, this is the hike
you chose. As far as it was beautiful, it was beautiful,
the pictures look great. We got lucky. So we did
the crawler's ledge section. It was perfect weather. If you
crossed it like the rain and it's all slippery and muddy,
that's when it's really really dangerous. But it's still like
it's just it's a body wide, single dirt path and
(08:19):
it's like, as long as you just stay on that path,
you're not gonna fall off the path. But I could
see why, like if you're if you get a wandering
eye and your eye wanders off to the side a
little bit and you can see, oh, there's a two
ft cliff over here. If I make one bad step,
then I could see how that gets in your head anyways.
So we were doing that and I kept encouraging her.
(08:40):
If she wanted to stop, we could stop, We could
turn around, we could go back to the trailhead, we
could find a hotel. And I was like, I was
kind of it was kind of like a reverse psychology thing.
I was thinking. I was like, if I tell her
we can return around, there's no way in how she's
gonna want to turn around. And there was like three
moments where I was like, Damn, she's really she's she
is really pushing herself here to the like to the utmost,
(09:03):
like to the full brink of what she can do.
And I swear to God, I was like, she's gonna
ask to turn around, and I would have had no
choice but to like turn around with her, and we
would have gone back and figured something else out. But um,
I do I like I did. I want to give
her as much credit as possible because it's easy for
me to do stuff like that because I'm not scared
of it. But it's much more challenging for someone that
is scared of it to still push through evan and
(09:26):
then do it. And she had no idea that I
was gonna engage too, So getting proposed, I guess, so, um,
like she's just thinking, what was going on a random hike?
And like I'd be pretty piste too if I was
doing something that I didn't really want to do for
some reason that I didn't really know, you know, did
you have a plan B? What if she was like, Dean,
(09:46):
I'm done, I'm turning around, we have to leave right now. Yeah,
I didn't have a plan B. But once she started
saying that she want to turn around, I started thinking
of what a plan B would have been. And I
don't think I really thought of anything good. So thankfully
there was no need for it. But so okay, So
on date. So we did through three nights. On the
first day we hiked halfway and slept. On the second
(10:09):
day was the day that I planned the proposing, and
so we finished the hike to the beach. We started
kind of early that day, at like seven am, and
then we got to the beach around like noon, and
so I was like, great, I've got six hours to
figure out where I want to propose, set up the camera,
do the whole spiel, the whole proposal spiel, and Caitlin,
(10:31):
fortunately for me, unfortunately for her, she was struggling, so
she laid down in the tent for like an hour
and took a nap and took some medicine. She had
a headache and her legs retired and all that stuff.
And I was like, great, this gives me time to
go out and explore figure out where I want to
do it because I've never been there before. I didn't
really know anything about it, and walked around scouted at
the location. I was like, Okay, cool, this is where
(10:53):
I want to do it. So I go back to
the campsite and um, she's like still struggling a little bit.
I was like, let me cook you some food. So
we cook her some food, and then an hour later,
it's like three pm, and I was like, let's just
take a nice walk on the beach. I found this
really cool spot. I want to get cute pictures of us,
and so she like walks down to the beach and
(11:13):
I was like, go stand over there near that rock
or like near those that rock wall, and she was like,
you want to walk all the way over there. I
was like, walk all the way over there. You've walked
eleven miles so far, what's another hundred feet? Anyways, so
she goes and stands out there and um start taking pictures.
And then I was like, okay, hang on one second,
I'm gonna set up the self timer. I'm gonna run
(11:33):
out there next to you. And then I like, go
out there next to her, give her the good side
because we both have the same good side, which is
pretty unfortunate for me. And uh, you've got a good side,
I imagine, right. Yeah, I like to be on my
I like to have my left showing, so do I
and so does Kalin. Yeah. I think that's everybody's good side.
Nobody likes to have their right Why is nobody like
(11:56):
this profile on there right? But everybody likes to have
their left profile. You wanna what's funny? Even you just
showing me those two profiles. I agree, your left side
is your good side. Yeah, my left side and my
good side. I don't know why. What is Ashley's a
good side? Uh? Her left, damn it? Yeah, her left?
Because every picture I was just thinking about pictures of
her and everything, she's on my left. So, no wonder
(12:18):
I don't like myself in pictures. I'm showing my poor side. Yeah,
and you probably didn't even realize that she's always snaking
the good side from me, and she just comes right up.
We'll swop off. So like if she's had the good
side for a couple of times, and I'll take the
good side, got it. But obviously an engagement, she gets
the good side. For this, I knew that I had
to give her the good side. So I ran out
(12:47):
there and I was like, oh, I saw this TikTok
trend where you stand facing away from each other and
then you count to three and you turn around. It's
like a fun candid shot and I have like there's
just a self time or like just taking a bunch
of a bunch of pictures every every second from are
far away. And so she's like three to one and
we turned around and jump and then I was like,
oh no, no, no, wait, we can do better than that.
(13:07):
And so then I turned back around and I grabbed
the ring out of my pocket and she's like three
to one and we jump around and I was on
one knee and I said, that's so sweet, man, it
was pretty cute. I guess I, um, yeah, I did
you know. Never thought this day would come. I never
thought I would uh propose to Miss North Carolina on
(13:30):
a beach in Hawaii, but here, we are here, we
are here, you are So what made you want to
choose that beach because you've never been there before? You
just maybe saw them pictures and said that's where I
want to propose. They kind of worked out in a
weird way. So we were we were in Oahu like
three or four months ago for a wedding and we
went to Kauai afterwards. And in Kauai we did like
(13:52):
a helicopter tour of the Neapoli coast. And I've always
my brother had done that hike like seven years ago,
and he's always raved about it. So I got on
the website and I looked at permits because you need
you need a reserve permits for the hike, and there
was a date window from October three to October and
I was like, wow, that's really cool because October is
(14:15):
a special date for me because that's like the anniversary
of my mom passing away. And so I saw those
dates on we were like booking the reservation on the
airplane as we were leaving Kauai that time for you know,
for three months in the future, and I was like,
you know what, that'd probably be a pretty pretty cool
time to propose, And so that's just kind of how
that sprung into action. Did you propose? Actually pretty cool
(14:39):
story too. So so is the anniversary of my mom
passing away. It's been sixteen years. And every time I
see a feather, I'm reminded that my mom is with
me in some way. Every time I go and do something, uh,
and there are feathers all over the place, so sure,
like whatever, I can find a feather wherever. Um. Every
time I'm doing something dangerous like rock climbing or skydiving
(15:01):
or something like, if I'm rock climbing, I'll come I'll
be like scared in a moment, and I'll like climb
up a little bit and I'll see a feather to
my right and I'm like, wow, cool, my mom is
watching me. I'm safe or or or she's with me.
So like I feel comfortable because I know she's here
with me. So I proposed to calin and I was like, oh,
this is cool cave over here. I want us to
go just explore that and cook around it for a
(15:22):
little bit. And I like go into the cave to
set up a picture real quick, and she's climbing up
this little sand dune and this perfect, full fluffy feather
just rolls right on by Caylin's feet and we and
there was never a feather on this beach or on
the hike up until this moment. The very first feather
we saw was ten minutes after I proposed, and so
I was like, oh my gosh, that's awesome. That's my
mom saying that she is with us and that she
(15:45):
approves of of what we're doing. So I was like,
that's really cool. So I kept a feather Calin's got
up for my birthday last year or something. She got
me a little display case for a special feather, which
is so random, like who gets a special display case
for a feather? And I was like, well, I don't
have just a random feather. That's so meaningful to me.
I want to put it in this case, But now
(16:06):
I do. Isn't that awesome that she just got it
out and she just showed it out? Uh so yeah,
so my mom approves. She is stoked. I'm stoked, and
Cayln is stoked. Um, but that's beautiful, man, that really is. Yeah,
it's it's pretty. It's pretty cool. I guess. Yeah, it's okay,
admitting that, you know, I mean it's to have your
(16:27):
subject and like to do it on you know, that day.
I don't know, it feels like almost uh certainly not
I mean it's not my place to say, but ah,
certainly not like turning the page. That's not what I
mean at all, But just like a really yeah, um,
great moment for you, uh right with your mom and Caitlyn. Yeah, sure,
(16:52):
I I appreciate you choosing your words carefully. They're not
that you can say anything that would make me like
offendit or anything like that. But but yeah, it was
a nice moment. You know. It's it's always a hard
time of year for me, this time of year because
I was get really depressed because I just be reminded
about how I lost her a long time ago, and
so I wanted to turn the memory of this day.
(17:16):
I wanted to be more positive and I want to
start associating that date with more positive things, and this
was my way of doing that. And I kind of
was thinking too as I was like going down there,
like there is a little bit of selfishness in that,
Like Cayle, probably, I don't know though, Like Caleen, I'm
sure it is very happy and would have taken it
(17:37):
on any day, and she loves being part of this.
But I do kind of feel like slightly selfish that
I'm like using her to cheer me up because my
mom's dad, you know, that's what she wants. I can't imagine,
Kalen would ever want you to not propose on your
mother's anniversary because you feel selfish. You know, Listen, when
(18:01):
you go into a relationship, you're in the relationship because
you love the other person. You want them to be happy,
and you want to be a part of the reason
why they're happy. And I think you proposing on that
specific day, I bet makes Kalin feel even more special. Yeah,
she did just wave her finger and she said, no,
it doesn't make me feel weird at all. Uh. And
(18:23):
then I told her, I was like, I want to
get married on until next year because I don't want
to be I don't want to have an engagement anniversary,
a wedding anniversary, of first day anniversary, the too many
do you celebrate all of those? Actually, just acknowledge them, dude. Actually,
Like throughout the year, she be She'll be like, oh,
today's the anniversary where we first met. I'm like, oh,
(18:44):
she's like, you don't remember. I'm like, no, I just
there's a lot, there's a lot to remember these days.
And then it's like, this is the day that we
got engaged, and I'm like, oh, yeah, yeah, it's that
time of June, isn't it. Okay, that's great. You know,
it's like how many anniverse suasan birthdays and holidays could
there possibly be? And she I told her, I said,
we have one anniversary now, that is it. It is
(19:06):
our wedding anniversary anniversary. That's the day. That's the day
we celebrate when you know, a nice little kiss, being like,
oh we got engaged five years ago. Great, love you, Okay,
moving on with my life. And what is the wedding anniversary?
August twelve, eleventh? Oh so close. So that was good, bro,
it was good August eleven. So not to talk about wedding,
(19:29):
but you're thinking October, h yeah. But then I told
Kyleen Matt and she was like, well, we can't do that.
We can't do that because next year October is a Tuesday,
and no one wants to go to a wedding on
a Tuesday. I mean, there would be nothing more dean
than to get married and get married on a Tuesday.
I would I love that so much. You make a
(19:51):
good point, um, so maybe we just do it like
the weekend before. I don't know exactly what we would do,
but we have a nervous venues will be cheap. East
And said, were you ever nervous that Calin was gonna say? No,
You're like, oh god, I'm really just taking her to
the brink of sanity with this hike. She might just
turn around and be like, I can't do this anymore. Dan.
(20:12):
She like, no, I can't marry you. I didn't do
a good enough job of putting into words how angry
she was at me that day. She I have never
seen her so angry in my entire life, and she like,
(20:32):
I don't even know. I don't even know how to
put it in the words now. She was so angry
at me. She for literally an hour an hour and
a half through this sketchy area. I was just sitting
there like, you've got this, nothing can stop you. You're
a beast, You're you're fearless, eceter like, just consistently like
trying to motivate her to like either distract her from
(20:54):
the scariness of the thing that was going on annoy
her to where she's more angry at me than she
is afraid of the high that's going on. And like,
I don't have direct quotes because I think I have
mentally pushed it out of my head because I don't
want to remember her that way at all. But she
she was she was just like why the like just
(21:15):
she was just losing. And so when she was losing
it during that difficult part of the hike, I was like, okay, um,
Like in my in my head, I'm like, well, I'm
gonna I'm gonna ask you to marry me in like
four hours, So you need to turn this attitude around. Yeah,
I need some more positivity from you. Okay. I was like,
I can't have my my fiancee just being miserable like
(21:38):
this and great, like obviously she's not gonna be miserable
like that forever for everything. But I was like, you gotta,
you gotta get together, sister, like you need to figure
this out. And then sure enough, Like it was funny
to see her her growth throughout the entire trip to
because like the hiking parts always suck and she's always
she was asking me, She's like, so you just do
(21:58):
this and you have fun when you hike. And like
I'm like, no, I hate hiking. Hiking sucks. But the
fun part is camping after the hike, or looking back
on the whole experience as a whole after the hike,
because then you have a lot of like a big
sense of accomplishment. But the hiking part really sucks. And
so she was complaining, I don't want to say complaining.
She she was voicing her concerns um throughout the entire
(22:21):
hiking portion. But every time we got to camp she
was smiling and laughing and you know, eating her mashed
potatoes and just relaxing and having a good time. It
was it was just during the hiking that that really
uh kind of threw off. The first two days and
then the last two days she did really great. But
then we got to camp and I made her some
food and she settled down, and I was like, okay, cool, now, um,
(22:42):
now we could do this. But but no, there was
never there was never a moment where I thought she
would say no. Although, like I said, when I when
I got to a knee and I proposed, she took
a long time to say yes. She took a real
long time to say yes. And I don't know, I
don't know what was going on in her head, but
it took a lot longer than I imagined. It takes
(23:03):
you to think about it for a second. Yeah she did.
And so we were up in like Tahoe for my
brother's proposal and we photographed it and my brother's wife
tackled him on the beach because she's so happy. And
after the proposed, after proposed to Kal and I was like, Hey,
why didn't you tackle me? Ross's wife tackled him on
(23:24):
the beach. You didn't even tackle me? What the heck?
Do you not want to marry me? Do you not
love me as much as Ross's wife loves him? Um,
but she made some good points. She's a tiny little
baby and she wouldn't even be able to tackle me
even if she tried a million times. Um. So yeah,
so that's that's basically that's basically that. And then oh
and then we popped a bottle of champagne on the beach,
(23:44):
which was really lovely, so bachelor of you. It was
pretty bachelor. I was thinking about bringing like one rose
or something, but uh, we had to do all all
aggresser shopping in Hawaii the day before and my backpack.
I'm like a pretty strong guy, and I think I'm
stronger now in terms of like my hiking ability than
I ever have been before. Like I can go further,
(24:07):
I can go longer, I can carry more. And my
intention this trip was to carry everything for both of
us for the entire four days and three nights. And
I feel as much as I could in my bag.
And then she had like a little overflow in hers
that weighed maybe like ten pounds my bag, I kid
you not wait a hundred pounds. And it was like
(24:29):
buying far the heaviest I've ever had a backpack away
in my entire life. Uh. And we got to the
campsite and I started pulling things out of it, and
I like pulled this big bottle of champagne out, uh,
this big bottle of spaghetti sauce, this bottle of hot sauce,
this salt and pepper shaker, this bottle of olive oil.
And I was like, no, wonder, my bag way so much.
(24:50):
I have all of this, like these glass bottles because
I wanted to like rather than use like dehydrated backpacking
meals for this trip. I wanted to because meals every
every time we ate, and the food was good. I I,
you know, I don't want to pet myself on the
back too much. But I did a pretty good job.
But it was so difficult because like the trails a
(25:12):
lot up and down through the like the coastline, and
it was, um, it was just really challenging, I guess
in that regard, But yeah, I don't know. I forget.
I forget where I was going with that one too.
I just keep going off on these tangents and I
forget what I'm talking about. Now. Your bag was so heavy.
Was the heaviest you ever had, heaviest I've ever had.
And then I told Kaylin to I was like, Kyllen,
I could drop this bag ahead and a mile come back.
(25:35):
I could literally throw you over my shoulder like a
fireman and carry you along this trail if you like.
There was a moment where I was like, per like
seriously considering doing that because she was too scared to move.
I was getting so impatient, and I was doing our
best to stay patient, but I was getting so impatient.
I was like, you have done this a million times.
Just imagine like there's not a big steep clip cliff
(25:55):
over here and you can walk on past it. And
she she understanding. He took her time, and I was like,
I'm gonna go drop my bag. Yeah, just pretend the
edge of death isn't right there. I was gonna put
her on like like I was gonna give her a
piggyback ride and wear her as a backpack because she
weighed as much as my backpack did and I knew
that I could do it. But anyways, point is, it
was the heaviest backpack I've ever won in my entire life. Um.
(26:19):
But at the end of the day, everything worked out
exactly as it should have, which is pretty fortunate because
you know, obviously a lot can go wrong in those
types of situations. So do you remember what you said
at all? Yeah? You know, I went back and forth
on whether I should have delivered like a nice romantic
speech as I proposed, because you did. Yeah. I just wanted,
(26:41):
you know, listen, I'm I'm a film junkie, so I
really wanted to make a moment out of it. So
I made sure that, you know, I pulled it to
the middle of the beach and the like gave this
speel of how I felt, but most of it I
didn't rehearse. It was more, honestly, just from the heart.
Can you give us a quick recap on what you
said to actually, because I will remember it. I just
want to remember, honestly, don't remember. I don't know. It
(27:02):
was just more of like I said, it was just
stuff from the heart about how much he meant to me,
and and uh, you know how far we've come, and um,
you know our hopes for the future. And that was
really it. Uh. And then I remember afterwards only from
watching it back. I don't remember saying it in in
(27:22):
real time, but apparently when I put the ring on,
it fit her and I said, just like Cinderella's slipper,
which is so stupid. I'll never forget. Watching that back,
I'm like, I can't believe I just said that. That's
pretty funny, smooth. I don't saying it, do you? So?
(27:45):
Do you? You did you give a spiel at all? Um? No,
I did it. I wasn't nervous at all. But the
reason I was able to not be nervous at all
was because I had already pre planned and to give
a speech, hm, like if I know, if I know,
she's gonna say, yes, I know what I'm supposed to do.
(28:07):
I know what I'm gonna do. Then there's nothing to
be nervous about. But if I were to give a
speech and say things that I would have like probably
end up regretting like Cinderella Slipper, then I knew that
I then I would have been nervous. And so I
was like, well, why don't I just not Why don't
I just cut the nerves out of it and I
just don't say anything and I'll just let this sick
(28:29):
second plan b Ring do the talking. Um. So, so no,
I didn't have a speech. Okay, Then you said, but
did you ask her? Did you say will you marry me?
I said, will you let me be your husband? I
did say will you marry me? But I wanted to
say will you let me be? I wanted to say
will you let me be your husband? But I was like,
(28:50):
she's old school. She wants me to say will you
marry me? And you've done so many non traditional things.
Just give her this one thing, will you marry me?
I'm glad you said that, very cool, so cute, and
like I said, she hesitated. She took her time to respond.
I was sitting there on one knee looking up at
her she was doing she like she was jumping around
a little bit, and I was like, are these happy jumps?
(29:11):
Are they sad jumps? What's going on? You trying to
jump away? Tell me what's going on? Yeah, what's going
on here? And then I guess what she was doing
when she was taking off her ring so that way
she could I could put the ring on her finger. Um.
And then yeah, and then we went over then to
the I can found that feather, which is great, and
then we went back to the campsite, popped the bottle
(29:33):
of champagne. She was steadfast and trying to hire like
a boat or a helicopter to come pick her up
because it's another eleven miles to get out. Yeah, I
got it. There's a couple other people on the beach,
like like locals that live on the beach, and I
was like, hey, guys, my girlfriend or my fiance is
having some health issues. She might need like an evac
(29:55):
via boat or helicopter. And they're like, well, we can
do that, but just so you know, like a helicopter
a thousand dollars a boat probably can't come. And so oh,
and if you take a helicopter, you have to go
to the hospital because it's like an emergency service kind
of thing. And I told her all this stuff, and
she was like, I'm not going to go to the hospital.
That's so embarrassing. And I was like, okay, well, your
only other option then is to hike out with me
(30:16):
eleven miles, and so she was like, okay, fine, and
so we hiked the eleven miles and I'll be honest,
I don't know if it was like the fresh fiance,
like pepping her step, but the next two days she
was an absolute beast. She she was hiking like I
was struggling to keep up with her. She was so fast.
We got to the scary section again and we can
(30:39):
blew through it, like she she took an hour and
a half to go half a mile the first time,
it took her ten minutes the second time, Like she
was a completely different person. That half cut diamond ring
gave her special powers. Bro No, well yeah, that too, obviously.
But I was like, listen, you're scared going in on
this way. I guarantee you when you come back this way,
(30:59):
you're gonna of like you're gonna have a lot less
fear about everything because you've already done it, and you've
already you're gonna be excited about finishing. And she literally
just plowed right through it. It It was so impressive. Um.
And and then we camped at the same camp site.
We camped the first night again, and I made us
a delicious meal of spaghetti and then we can't We
hiked out the next day. And that last day really sucked,
actually because it rained a lot the last day, which
(31:22):
was in hindsight a good thing because if it had
rained the day before when we were doing the dangerous part,
then that would have been like pretty sketchy. But it
rained pretty hard on the last day, so we hid
like for five hours in the pouring rain, in the
slippery mud. Um. But yeah, we made it out, and
then we went to a nice, uh five star hotel
and took showers and now we're here. Very cool. Man. Well, congratulations,
(31:59):
that's very exciting. Now your fiance, I am a fiance,
but I still have a wedding ring on, so yeah,
you're pretty much a husband. You've been pretty much a
husband for quite some time now. I feel like a
fiance by title lonely, you know what, I mean like,
nothing feels different. No, it's the same thing, just still dating.
And let me ask you this. Do I when I
(32:20):
go out places and like, let's say I'm sitting, I'm
I'm uh, let's say Caitlin's parking the car and I'm
getting us a table at dinner. Do I say my
fiance and I are gonna eat? Or do I say
my girlfriend and I fiance? You guys are fiances? Is
that what you did? Yeah, there's only so much time
(32:40):
that your fiance you might as well take advantage of it. Yeah,
it just it just kind of seems pompous to me.
You know, yeah, a little bit, but you might get
like some free drinks out of it. Sometimes you're like, oh,
that your fiance's You guys are engaged. Congratulations first rounds
on us. When we checked into the hotel. Um. I
can't remember what the guy was saying, but he was like, uh,
(33:01):
he's like he didn't even ask if we were celebrating
a special occasion. But I made sure to let him
know that we just got engaged like two days before,
like praying he would upgrade us to like the honeymoon
suite or something like that didn't work. And he didn't
give it. He didn't give a single funck bastard. He
gave us a free He did give us a free
bottle of house champagne, which was very nice. Hey, there
we go. He probably does that to everybody. Um, but
(33:22):
that doesn't matter. You keep using that fiance. I guarantee
one of these days will pay off. Yeah. Um, wait
till you guys are married and you say your new
luwits you're gonna get everything free, And then what do
you do after that? Then you just say we allays
had a kid and then you get everything for free.
Um yeah, but then you start like not sleeping and
(33:44):
then in constant state of anxiety and stress. So you're like, oh,
it's cool that we got things for free, but now
it's not cool. Now it's not cool. Yeah, but you've
got a cute little baby to show for us. I
know he's the best, and uh he's dressing up for
Halloween right now, so he Um, it's pretty cool. He's awesome.
But Dean, congratulations, man, So exciting for you and Klin.
(34:06):
You and Klin definitely has to come on this podcast
talk about her side of the story, because I have
a feeling it's going to be wildly different. Yeah, I mean,
it'll probably be a lot more realistic. Yeah, you know,
I know, but I'm I'm excited to hear that tale. Yeah, she'll, she'll,
she'll do it. Um, I didn't want to have her
to come on this episode. I wanted it. Uh, maybe
(34:29):
we'll have her in on like the next couple of
weeks or something like that. But but yeah, she well,
so she's supposed to propose to me now too. Oh yeah,
I forgot about that. That was the deal that we
would propose to each other. Is that still planned? I
think so. She she said, my ring isn't ready yet,
but she was so certain that she was going to
propose to me before I proposed to her. Obviously that
(34:51):
didn't happen because I've already proposed to her. But she's
said before the end of the year, so she's only
got two months, two months and a week left. Um,
but we'll see how that goes. I guess that's yeah,
I forgot about that. Yes, you guys have another proposal coming.
I wonder where she's gonna do it. I don't necessarily
need one at this point. She's it was just basically
(35:11):
steal my thunder from me for proposing to her. Yeah,
that would be a selfish move. That would be a
selfish move. I didn't realize how much power is bestowed
upon you by being the one to propose. Yeah, you
know what I mean? Like you like like now, Kalin
(35:31):
can't get angry at me, or actually couldn't get angry
at you because you're like, well, I just asked you
to marry me and you said yes, So like what
is there to be upset about? Like not like and
I'm talking like just like an everyday things like oh
I didn't clean my dishes, Well, too bad, because I've
already asked you to marry me and you're marrying me. Yeah,
you signed up for this, You signed on for this. Yeah,
so who knows. But we go to Galapagos tomorrow, oh
(35:54):
today actually, and maybe she'll do it there. You guys
don't stop. Well, we'll be on the lookout for another
agement for Dean and Kaylin. Also a quick shout out
to grocery store Joe and Serena, who officially got married
the same day, which was crazy the same day you
guys announced at least um so crazy. It just shows
that paradise rules them. All, um, so quick, congratulations to
(36:16):
two wonderful people, Joe and Serena. Wish you nothing, but
what about what about the confirmed news today? It's just
so frustrating and so maddening, and like people it's people
wonder like what's going on with Tom? What's going on
with Tom? It's like, really, you have to ask why Tom.
Maybe he isn't playing to the highest level he's used to,
(36:38):
Like the dude didn't play. He played okay last night,
but it's like he knew he was signing the papers
this morning. How could you even think about football last night?
So it sucks. I'm I have a lot of strong
feelings about this. Uh that will dive into on a
separate episode because we're leaving off on a happy note here,
not an angry note. Um, but uh, you know, as always,
(37:03):
I'm team Tom. I just don't understand if one one
last parting piece of wisdom here, if the two most
beautiful people in the world, the two most successful people
in the world, can't make it work, how is there
supposed to be any help for the rest of us. Yeah,
love is dead. Love is dead. There's no hope for
any of us. But you know, hey, whatever congratulations on
getting engaged. You know that's cool. Whatever, Thanks anytime. We'll
(37:30):
make sure you guys tune in next week with this
episode is coming out Sunday. Sunday everyone, Happy football Day. Uh.
And then Tuesday we also have our episode with Olivia
Creedy which is coming out. And then Thursday, of course
we have our Caller episode as well, so tune in
for those and make sure you tune in next week.
We're hopefully we all suck a little less. Dean sucks
a little less now for now, follow help by Suck
(37:51):
at Dating on I Heart Radio or wherever you listen
to podcast
Hell I Suck At Dating with Dean Anglert and Dared
Haven and I heard radio podcast. Hey, welcome to a
very very very special episode of Help I Suck At Dating.
(00:23):
We've been doing this podcast for quite some time now,
and throughout that time, uh, you have seen both Dean
and myself be single. You have seen us both being
committed relationships from paradise. You have seen me get engaged
married and have our wonderful little boy, Dawson. And now
(00:47):
on this episode today, October two thousand and twenty two,
whatever episode it is of Help I Second Dating, we
can say that Dean Angler Deanie Babies is engaged to
Kaylin Miller. Keys. Have a round of applause, ladies and gentlemen. Yeah, Dean,
(01:08):
how you doing, buddy? Congratulations? Well, first off, Jared, you
look twenty years younger right now because I shaved. I
don't think i've seen your cheek or your jaw bones
in five years. I mean it's been at least that long.
So we did Batman for Halloween, so I had to
shave down really show off the jaw. You know, I
gotta gotta get myself into that Robert Pattinson mode. But
(01:30):
this is not about me. It's not about me shaving
or looking young or tired or dead on the inside.
This is about you. Uh, dean, dude. Congratulations, man, it's awesome.
You're engaged. Dude, you're engaged your fiance. Yeah, I know,
we're engaged. It doesn't feel any different though, to be
(01:51):
honest with you, because I've already worn the wedding ring
for three years, we have already owned a house together
for two years. But don't get me wrong, it is beautiful.
I am very happy be engaged. Um. I know there's
always been a lot of like questions about whether we
just secretly eloped and got married to each other, And
so that's kind of why it's like, while I do
(02:12):
feel different and happy and excited, it doesn't I don't know,
it doesn't. It doesn't if it doesn't feel like there
was like it wasn't as big of a step as
like a normal relationship would have taken. Because we've already
taken that big step. I feel like, you know, So
my first question to you is did you actually lose
the ring or was that a whole lie that you had.
(02:34):
I saw people like commenting that I I have lost it.
If I have lost the ring. I am going to
find it. Uh. It's funny because I asked Kalin with
I got like a cute little half carrot diamond and
like like not in an emerald cut because I don't
think you can make an emerald cut ring that's small.
And ask Kalin and it's like holding the ring up
(02:58):
and she like leaned over and put her hands on
her knees and like looking at it. And I wasn't
sure if she was looking at it because she wanted
to see if it was like the ring that I
claimed to have lost, or if she was just sizing
it up or whatever. And I like felt kind of insecure,
like she was like staring at it um and then
sure enough it was just she was like taking off
her ring that she was wearing so I could put
that ring on her. But then she was like, let's
(03:19):
take pictures of it, like we were like the beach
at sunset, and I was like, I don't want to
take pictures of this ring because I'm embarrassed by how
small it is. It don't be embarrassing. I mean you
should be embarrassed you lost the ring, not by the
size of the new ring. Yeah, well I am I
am embarrassed by both things. And the new ring is
cool too. I was like talking to the guy about
it from He was like, yeah, once you find the
old ring, you can just bring this one back and
(03:40):
we'll turn into like a necklace or something. So I've
decided if I find the new the old ring, then
I'll get the new ring made into a necklace for me. Obviously,
would you wear it as that'd be kind of cute
if you wore it as a necklace. Yeah. And then
I was thinking too, instead of getting her an engagement ring,
I wanted to get her an engagement necklace. That way
we didn't have to trans any diamond at all. But
(04:01):
then I was like, no, that's a little too abstract.
I'm gonna stick with the ring. I'm gonna keep it
a little traditional. I guess what you could do is
you could turn the ring that you actually proposed with
into a necklace, like you said, and have it be
like a family heirloom. So if you guys decided to
have kids, you could pass that down and say this
is the actual diamond that I proposed to your mother with,
(04:22):
and then this is the one that I lost, and
this is the one that I lost the big gass
one is the one that I lost. So she wears
the mom wears that one. Yeah, Mom, because she's not
gonna lose that one. Um. Yeah. So that was how
that all went. I um uh, it was a fun hike.
I want to get Kalin on here at something. Yeah,
I want Kalin on here too. My question is, do
(04:42):
you for you did an eleven mile hike? Did you
do that on purpose because you really wanted her just
to be It's the most deean thing to have her
be completely exhausted, sweaty, tired, annoyed at you, And then
that's when you just turned it all around and propose.
I figured I've tested her so much, there had to
have been one final test for her. So she survives,
(05:03):
she gets the ring, and she passed. She passed the
test barely, though there were times. There were time I
don't want to have her on this podcast episode, but
I do want to have her on at some point
in the future and have her like recount her experience
because my experience and her experience are gonna be very different.
We So it's eleven miles and the weather was perfect,
(05:24):
it was beautiful, sunny, well, it was twenty two miles.
I guess she's because it's eleven miles in and eleven
miles out, and so there's like a halfway point that
you can hike too, so it's six miles in in camp,
and then you finished the next five miles the next day.
And so the first day we get it, we kind
of start late because we had a couple of things
(05:45):
to do in the morning, and then we start hiking
and then we get to the halfway point and we're like, wow,
that was a tough day, but we're here. Let's cook
some food. I cooked us up some sausages and some vegetables.
It was delicious. And then we woke up the next
day and started the next part of the trek. And
that part is like the infamous part of the trek.
It's called Crawler's Ledge. It's like a mile long track
(06:08):
of like sheer cliff on one side. And I I
personally thought it was fine. I didn't have an issue
with it. I want to I can't stress that enough.
I didn't have an issue with it. Um Kalin, on
the other hand, the other party did have an issue
with it. Yes. Kalin on the other hand, was very
(06:30):
angry at me for taking her there. She asked if
we could turn around fifty five times, and eventually I
just started saying, yeah, let's turn around. If you want
to turn around, let's turn around. And but she didn't.
I mean credit to her, because she was crying, she
was angry, she was cursing at me, but she stuck
(06:51):
with it and she eventually finished it. Um, so yeah,
it was. It was a it was a trying experience.
It's I was thinking, too, it's pretty funny, um to
make the person that you're gonna ask to marry you
cry on the day that you're going to propose to them.
Cried for like a like an hour that day. You
want to make them cry, but you don't want to
(07:11):
make them cry out of pain and sheer sadness. You know,
it's supposed to be happy tears that day, right. And
I did everything too. I like, I moved all of
her stuff into my backpack so she didn't need to
wear a backpack. I walked ahead a mile, put my
backpack down, came back with no backpack. That way I
could like like spot her as she moved along the cliffs.
(07:32):
I was doing everything. I was working over time. I
was trying to encourage her as best I can. But
it wasn't I mean, it was scary. They were scary
points I could see, like I could see someone getting
scared in those points, in those moments when you would
say it was scary, Do you think it was scary
because they she could have died. Yeah, she could have died.
Oh my god, you're an insane man. People die on
(07:55):
this hike like semi regularly. Um, this is the hike
you chose. As far as it was beautiful, it was beautiful,
the pictures look great. We got lucky. So we did
the crawler's ledge section. It was perfect weather. If you
crossed it like the rain and it's all slippery and muddy,
that's when it's really really dangerous. But it's still like
it's just it's a body wide, single dirt path and
(08:19):
it's like, as long as you just stay on that path,
you're not gonna fall off the path. But I could
see why, like if you're if you get a wandering
eye and your eye wanders off to the side a
little bit and you can see, oh, there's a two
ft cliff over here. If I make one bad step,
then I could see how that gets in your head anyways.
So we were doing that and I kept encouraging her.
(08:40):
If she wanted to stop, we could stop, We could
turn around, we could go back to the trailhead, we
could find a hotel. And I was like, I was
kind of it was kind of like a reverse psychology thing.
I was thinking. I was like, if I tell her
we can return around, there's no way in how she's
gonna want to turn around. And there was like three
moments where I was like, Damn, she's really she's she
is really pushing herself here to the like to the utmost,
(09:03):
like to the full brink of what she can do.
And I swear to God, I was like, she's gonna
ask to turn around, and I would have had no
choice but to like turn around with her, and we
would have gone back and figured something else out. But um,
I do I like I did. I want to give
her as much credit as possible because it's easy for
me to do stuff like that because I'm not scared
of it. But it's much more challenging for someone that
is scared of it to still push through evan and
(09:26):
then do it. And she had no idea that I
was gonna engage too, So getting proposed, I guess, so, um,
like she's just thinking, what was going on a random hike?
And like I'd be pretty piste too if I was
doing something that I didn't really want to do for
some reason that I didn't really know, you know, did
you have a plan B? What if she was like, Dean,
(09:46):
I'm done, I'm turning around, we have to leave right now. Yeah,
I didn't have a plan B. But once she started
saying that she want to turn around, I started thinking
of what a plan B would have been. And I
don't think I really thought of anything good. So thankfully
there was no need for it. But so okay, So
on date. So we did through three nights. On the
first day we hiked halfway and slept. On the second
(10:09):
day was the day that I planned the proposing, and
so we finished the hike to the beach. We started
kind of early that day, at like seven am, and
then we got to the beach around like noon, and
so I was like, great, I've got six hours to
figure out where I want to propose, set up the camera,
do the whole spiel, the whole proposal spiel, and Caitlin,
(10:31):
fortunately for me, unfortunately for her, she was struggling, so
she laid down in the tent for like an hour
and took a nap and took some medicine. She had
a headache and her legs retired and all that stuff.
And I was like, great, this gives me time to
go out and explore figure out where I want to
do it because I've never been there before. I didn't
really know anything about it, and walked around scouted at
the location. I was like, Okay, cool, this is where
(10:53):
I want to do it. So I go back to
the campsite and um, she's like still struggling a little bit.
I was like, let me cook you some food. So
we cook her some food, and then an hour later,
it's like three pm, and I was like, let's just
take a nice walk on the beach. I found this
really cool spot. I want to get cute pictures of us,
and so she like walks down to the beach and
(11:13):
I was like, go stand over there near that rock
or like near those that rock wall, and she was like,
you want to walk all the way over there. I
was like, walk all the way over there. You've walked
eleven miles so far, what's another hundred feet? Anyways, so
she goes and stands out there and um start taking pictures.
And then I was like, okay, hang on one second,
I'm gonna set up the self timer. I'm gonna run
(11:33):
out there next to you. And then I like, go
out there next to her, give her the good side
because we both have the same good side, which is
pretty unfortunate for me. And uh, you've got a good side,
I imagine, right. Yeah, I like to be on my
I like to have my left showing, so do I
and so does Kalin. Yeah. I think that's everybody's good side.
Nobody likes to have their right Why is nobody like
(11:56):
this profile on there right? But everybody likes to have
their left profile. You wanna what's funny? Even you just
showing me those two profiles. I agree, your left side
is your good side. Yeah, my left side and my
good side. I don't know why. What is Ashley's a
good side? Uh? Her left, damn it? Yeah, her left?
Because every picture I was just thinking about pictures of
her and everything, she's on my left. So, no wonder
(12:18):
I don't like myself in pictures. I'm showing my poor side. Yeah,
and you probably didn't even realize that she's always snaking
the good side from me, and she just comes right up.
We'll swop off. So like if she's had the good
side for a couple of times, and I'll take the
good side, got it. But obviously an engagement, she gets
the good side. For this, I knew that I had
to give her the good side. So I ran out
(12:47):
there and I was like, oh, I saw this TikTok
trend where you stand facing away from each other and
then you count to three and you turn around. It's
like a fun candid shot and I have like there's
just a self time or like just taking a bunch
of a bunch of pictures every every second from are
far away. And so she's like three to one and
we turned around and jump and then I was like,
oh no, no, no, wait, we can do better than that.
(13:07):
And so then I turned back around and I grabbed
the ring out of my pocket and she's like three
to one and we jump around and I was on
one knee and I said, that's so sweet, man, it
was pretty cute. I guess I, um, yeah, I did
you know. Never thought this day would come. I never
thought I would uh propose to Miss North Carolina on
(13:30):
a beach in Hawaii, but here, we are here, we
are here, you are So what made you want to
choose that beach because you've never been there before? You
just maybe saw them pictures and said that's where I
want to propose. They kind of worked out in a
weird way. So we were we were in Oahu like
three or four months ago for a wedding and we
went to Kauai afterwards. And in Kauai we did like
(13:52):
a helicopter tour of the Neapoli coast. And I've always
my brother had done that hike like seven years ago,
and he's always raved about it. So I got on
the website and I looked at permits because you need
you need a reserve permits for the hike, and there
was a date window from October three to October and
I was like, wow, that's really cool because October is
(14:15):
a special date for me because that's like the anniversary
of my mom passing away. And so I saw those
dates on we were like booking the reservation on the
airplane as we were leaving Kauai that time for you know,
for three months in the future, and I was like,
you know what, that'd probably be a pretty pretty cool
time to propose, And so that's just kind of how
that sprung into action. Did you propose? Actually pretty cool
(14:39):
story too. So so is the anniversary of my mom
passing away. It's been sixteen years. And every time I
see a feather, I'm reminded that my mom is with
me in some way. Every time I go and do something, uh,
and there are feathers all over the place, so sure,
like whatever, I can find a feather wherever. Um. Every
time I'm doing something dangerous like rock climbing or skydiving
(15:01):
or something like, if I'm rock climbing, I'll come I'll
be like scared in a moment, and I'll like climb
up a little bit and I'll see a feather to
my right and I'm like, wow, cool, my mom is
watching me. I'm safe or or or she's with me.
So like I feel comfortable because I know she's here
with me. So I proposed to calin and I was like, oh,
this is cool cave over here. I want us to
go just explore that and cook around it for a
(15:22):
little bit. And I like go into the cave to
set up a picture real quick, and she's climbing up
this little sand dune and this perfect, full fluffy feather
just rolls right on by Caylin's feet and we and
there was never a feather on this beach or on
the hike up until this moment. The very first feather
we saw was ten minutes after I proposed, and so
I was like, oh my gosh, that's awesome. That's my
mom saying that she is with us and that she
(15:45):
approves of of what we're doing. So I was like,
that's really cool. So I kept a feather Calin's got
up for my birthday last year or something. She got
me a little display case for a special feather, which
is so random, like who gets a special display case
for a feather? And I was like, well, I don't
have just a random feather. That's so meaningful to me.
I want to put it in this case, But now
(16:06):
I do. Isn't that awesome that she just got it
out and she just showed it out? Uh so yeah,
so my mom approves. She is stoked. I'm stoked, and
Cayln is stoked. Um, but that's beautiful, man, that really is. Yeah,
it's it's pretty. It's pretty cool. I guess. Yeah, it's okay,
admitting that, you know, I mean it's to have your
(16:27):
subject and like to do it on you know, that day.
I don't know, it feels like almost uh certainly not
I mean it's not my place to say, but ah,
certainly not like turning the page. That's not what I
mean at all, But just like a really yeah, um,
great moment for you, uh right with your mom and Caitlyn. Yeah, sure,
(16:52):
I I appreciate you choosing your words carefully. They're not
that you can say anything that would make me like
offendit or anything like that. But but yeah, it was
a nice moment. You know. It's it's always a hard
time of year for me, this time of year because
I was get really depressed because I just be reminded
about how I lost her a long time ago, and
so I wanted to turn the memory of this day.
(17:16):
I wanted to be more positive and I want to
start associating that date with more positive things, and this
was my way of doing that. And I kind of
was thinking too as I was like going down there,
like there is a little bit of selfishness in that,
Like Cayle, probably, I don't know though, Like Caleen, I'm
sure it is very happy and would have taken it
(17:37):
on any day, and she loves being part of this.
But I do kind of feel like slightly selfish that
I'm like using her to cheer me up because my
mom's dad, you know, that's what she wants. I can't imagine,
Kalen would ever want you to not propose on your
mother's anniversary because you feel selfish. You know, Listen, when
(18:01):
you go into a relationship, you're in the relationship because
you love the other person. You want them to be happy,
and you want to be a part of the reason
why they're happy. And I think you proposing on that
specific day, I bet makes Kalin feel even more special. Yeah,
she did just wave her finger and she said, no,
it doesn't make me feel weird at all. Uh. And
(18:23):
then I told her, I was like, I want to
get married on until next year because I don't want
to be I don't want to have an engagement anniversary,
a wedding anniversary, of first day anniversary, the too many
do you celebrate all of those? Actually, just acknowledge them, dude. Actually,
Like throughout the year, she be She'll be like, oh,
today's the anniversary where we first met. I'm like, oh,
(18:44):
she's like, you don't remember. I'm like, no, I just
there's a lot, there's a lot to remember these days.
And then it's like, this is the day that we
got engaged, and I'm like, oh, yeah, yeah, it's that
time of June, isn't it. Okay, that's great. You know,
it's like how many anniverse suasan birthdays and holidays could
there possibly be? And she I told her, I said,
we have one anniversary now, that is it. It is
(19:06):
our wedding anniversary anniversary. That's the day. That's the day
we celebrate when you know, a nice little kiss, being like,
oh we got engaged five years ago. Great, love you, Okay,
moving on with my life. And what is the wedding anniversary?
August twelve, eleventh? Oh so close. So that was good, bro,
it was good August eleven. So not to talk about wedding,
(19:29):
but you're thinking October, h yeah. But then I told
Kyleen Matt and she was like, well, we can't do that.
We can't do that because next year October is a Tuesday,
and no one wants to go to a wedding on
a Tuesday. I mean, there would be nothing more dean
than to get married and get married on a Tuesday.
I would I love that so much. You make a
(19:51):
good point, um, so maybe we just do it like
the weekend before. I don't know exactly what we would do,
but we have a nervous venues will be cheap. East
And said, were you ever nervous that Calin was gonna say? No,
You're like, oh god, I'm really just taking her to
the brink of sanity with this hike. She might just
turn around and be like, I can't do this anymore. Dan.
(20:12):
She like, no, I can't marry you. I didn't do
a good enough job of putting into words how angry
she was at me that day. She I have never
seen her so angry in my entire life, and she like,
(20:32):
I don't even know. I don't even know how to
put it in the words now. She was so angry
at me. She for literally an hour an hour and
a half through this sketchy area. I was just sitting
there like, you've got this, nothing can stop you. You're
a beast, You're you're fearless, eceter like, just consistently like
trying to motivate her to like either distract her from
(20:54):
the scariness of the thing that was going on annoy
her to where she's more angry at me than she
is afraid of the high that's going on. And like,
I don't have direct quotes because I think I have
mentally pushed it out of my head because I don't
want to remember her that way at all. But she
she was she was just like why the like just
(21:15):
she was just losing. And so when she was losing
it during that difficult part of the hike, I was like, okay, um,
Like in my in my head, I'm like, well, I'm
gonna I'm gonna ask you to marry me in like
four hours, So you need to turn this attitude around. Yeah,
I need some more positivity from you. Okay. I was like,
I can't have my my fiancee just being miserable like
(21:38):
this and great, like obviously she's not gonna be miserable
like that forever for everything. But I was like, you gotta,
you gotta get together, sister, like you need to figure
this out. And then sure enough, Like it was funny
to see her her growth throughout the entire trip to
because like the hiking parts always suck and she's always
she was asking me, She's like, so you just do
(21:58):
this and you have fun when you hike. And like
I'm like, no, I hate hiking. Hiking sucks. But the
fun part is camping after the hike, or looking back
on the whole experience as a whole after the hike,
because then you have a lot of like a big
sense of accomplishment. But the hiking part really sucks. And
so she was complaining, I don't want to say complaining.
She she was voicing her concerns um throughout the entire
(22:21):
hiking portion. But every time we got to camp she
was smiling and laughing and you know, eating her mashed
potatoes and just relaxing and having a good time. It
was it was just during the hiking that that really
uh kind of threw off. The first two days and
then the last two days she did really great. But
then we got to camp and I made her some
food and she settled down, and I was like, okay, cool, now, um,
(22:42):
now we could do this. But but no, there was
never there was never a moment where I thought she
would say no. Although, like I said, when I when
I got to a knee and I proposed, she took
a long time to say yes. She took a real
long time to say yes. And I don't know, I
don't know what was going on in her head, but
it took a lot longer than I imagined. It takes
(23:03):
you to think about it for a second. Yeah she did.
And so we were up in like Tahoe for my
brother's proposal and we photographed it and my brother's wife
tackled him on the beach because she's so happy. And
after the proposed, after proposed to Kal and I was like, Hey,
why didn't you tackle me? Ross's wife tackled him on
(23:24):
the beach. You didn't even tackle me? What the heck?
Do you not want to marry me? Do you not
love me as much as Ross's wife loves him? Um,
but she made some good points. She's a tiny little
baby and she wouldn't even be able to tackle me
even if she tried a million times. Um. So yeah,
so that's that's basically that's basically that. And then oh
and then we popped a bottle of champagne on the beach,
(23:44):
which was really lovely, so bachelor of you. It was
pretty bachelor. I was thinking about bringing like one rose
or something, but uh, we had to do all all
aggresser shopping in Hawaii the day before and my backpack.
I'm like a pretty strong guy, and I think I'm
stronger now in terms of like my hiking ability than
I ever have been before. Like I can go further,
(24:07):
I can go longer, I can carry more. And my
intention this trip was to carry everything for both of
us for the entire four days and three nights. And
I feel as much as I could in my bag.
And then she had like a little overflow in hers
that weighed maybe like ten pounds my bag, I kid
you not wait a hundred pounds. And it was like
(24:29):
buying far the heaviest I've ever had a backpack away
in my entire life. Uh. And we got to the
campsite and I started pulling things out of it, and
I like pulled this big bottle of champagne out, uh,
this big bottle of spaghetti sauce, this bottle of hot sauce,
this salt and pepper shaker, this bottle of olive oil.
And I was like, no, wonder, my bag way so much.
(24:50):
I have all of this, like these glass bottles because
I wanted to like rather than use like dehydrated backpacking
meals for this trip. I wanted to because meals every
every time we ate, and the food was good. I I,
you know, I don't want to pet myself on the
back too much. But I did a pretty good job.
But it was so difficult because like the trails a
(25:12):
lot up and down through the like the coastline, and
it was, um, it was just really challenging, I guess
in that regard, But yeah, I don't know. I forget.
I forget where I was going with that one too.
I just keep going off on these tangents and I
forget what I'm talking about. Now. Your bag was so heavy.
Was the heaviest you ever had, heaviest I've ever had.
And then I told Kaylin to I was like, Kyllen,
I could drop this bag ahead and a mile come back.
(25:35):
I could literally throw you over my shoulder like a
fireman and carry you along this trail if you like.
There was a moment where I was like, per like
seriously considering doing that because she was too scared to move.
I was getting so impatient, and I was doing our
best to stay patient, but I was getting so impatient.
I was like, you have done this a million times.
Just imagine like there's not a big steep clip cliff
(25:55):
over here and you can walk on past it. And
she she understanding. He took her time, and I was like,
I'm gonna go drop my bag. Yeah, just pretend the
edge of death isn't right there. I was gonna put
her on like like I was gonna give her a
piggyback ride and wear her as a backpack because she
weighed as much as my backpack did and I knew
that I could do it. But anyways, point is, it
was the heaviest backpack I've ever won in my entire life. Um.
(26:19):
But at the end of the day, everything worked out
exactly as it should have, which is pretty fortunate because
you know, obviously a lot can go wrong in those
types of situations. So do you remember what you said
at all? Yeah? You know, I went back and forth
on whether I should have delivered like a nice romantic
speech as I proposed, because you did. Yeah. I just wanted,
(26:41):
you know, listen, I'm I'm a film junkie, so I
really wanted to make a moment out of it. So
I made sure that, you know, I pulled it to
the middle of the beach and the like gave this
speel of how I felt, but most of it I
didn't rehearse. It was more, honestly, just from the heart.
Can you give us a quick recap on what you
said to actually, because I will remember it. I just
want to remember, honestly, don't remember. I don't know. It
(27:02):
was just more of like I said, it was just
stuff from the heart about how much he meant to me,
and and uh, you know how far we've come, and um,
you know our hopes for the future. And that was
really it. Uh. And then I remember afterwards only from
watching it back. I don't remember saying it in in
(27:22):
real time, but apparently when I put the ring on,
it fit her and I said, just like Cinderella's slipper,
which is so stupid. I'll never forget. Watching that back,
I'm like, I can't believe I just said that. That's
pretty funny, smooth. I don't saying it, do you? So?
(27:45):
Do you? You did you give a spiel at all? Um? No,
I did it. I wasn't nervous at all. But the
reason I was able to not be nervous at all
was because I had already pre planned and to give
a speech, hm, like if I know, if I know,
she's gonna say, yes, I know what I'm supposed to do.
(28:07):
I know what I'm gonna do. Then there's nothing to
be nervous about. But if I were to give a
speech and say things that I would have like probably
end up regretting like Cinderella Slipper, then I knew that
I then I would have been nervous. And so I
was like, well, why don't I just not Why don't
I just cut the nerves out of it and I
just don't say anything and I'll just let this sick
(28:29):
second plan b Ring do the talking. Um. So, so no,
I didn't have a speech. Okay, Then you said, but
did you ask her? Did you say will you marry me?
I said, will you let me be your husband? I
did say will you marry me? But I wanted to
say will you let me be? I wanted to say
will you let me be your husband? But I was like,
(28:50):
she's old school. She wants me to say will you
marry me? And you've done so many non traditional things.
Just give her this one thing, will you marry me?
I'm glad you said that, very cool, so cute, and
like I said, she hesitated. She took her time to respond.
I was sitting there on one knee looking up at
her she was doing she like she was jumping around
a little bit, and I was like, are these happy jumps?
(29:11):
Are they sad jumps? What's going on? You trying to
jump away? Tell me what's going on? Yeah, what's going
on here? And then I guess what she was doing
when she was taking off her ring so that way
she could I could put the ring on her finger. Um.
And then yeah, and then we went over then to
the I can found that feather, which is great, and
then we went back to the campsite, popped the bottle
(29:33):
of champagne. She was steadfast and trying to hire like
a boat or a helicopter to come pick her up
because it's another eleven miles to get out. Yeah, I
got it. There's a couple other people on the beach,
like like locals that live on the beach, and I
was like, hey, guys, my girlfriend or my fiance is
having some health issues. She might need like an evac
(29:55):
via boat or helicopter. And they're like, well, we can
do that, but just so you know, like a helicopter
a thousand dollars a boat probably can't come. And so oh,
and if you take a helicopter, you have to go
to the hospital because it's like an emergency service kind
of thing. And I told her all this stuff, and
she was like, I'm not going to go to the hospital.
That's so embarrassing. And I was like, okay, well, your
only other option then is to hike out with me
(30:16):
eleven miles, and so she was like, okay, fine, and
so we hiked the eleven miles and I'll be honest,
I don't know if it was like the fresh fiance,
like pepping her step, but the next two days she
was an absolute beast. She she was hiking like I
was struggling to keep up with her. She was so fast.
We got to the scary section again and we can
(30:39):
blew through it, like she she took an hour and
a half to go half a mile the first time,
it took her ten minutes the second time, Like she
was a completely different person. That half cut diamond ring
gave her special powers. Bro No, well yeah, that too, obviously.
But I was like, listen, you're scared going in on
this way. I guarantee you when you come back this way,
(30:59):
you're gonna of like you're gonna have a lot less
fear about everything because you've already done it, and you've
already you're gonna be excited about finishing. And she literally
just plowed right through it. It It was so impressive. Um.
And and then we camped at the same camp site.
We camped the first night again, and I made us
a delicious meal of spaghetti and then we can't We
hiked out the next day. And that last day really sucked,
actually because it rained a lot the last day, which
(31:22):
was in hindsight a good thing because if it had
rained the day before when we were doing the dangerous part,
then that would have been like pretty sketchy. But it
rained pretty hard on the last day, so we hid
like for five hours in the pouring rain, in the
slippery mud. Um. But yeah, we made it out, and
then we went to a nice, uh five star hotel
and took showers and now we're here. Very cool. Man. Well, congratulations,
(31:59):
that's very exciting. Now your fiance, I am a fiance,
but I still have a wedding ring on, so yeah,
you're pretty much a husband. You've been pretty much a
husband for quite some time now. I feel like a
fiance by title lonely, you know what, I mean like,
nothing feels different. No, it's the same thing, just still dating.
And let me ask you this. Do I when I
(32:20):
go out places and like, let's say I'm sitting, I'm
I'm uh, let's say Caitlin's parking the car and I'm
getting us a table at dinner. Do I say my
fiance and I are gonna eat? Or do I say
my girlfriend and I fiance? You guys are fiances? Is
that what you did? Yeah, there's only so much time
(32:40):
that your fiance you might as well take advantage of it. Yeah,
it just it just kind of seems pompous to me.
You know, yeah, a little bit, but you might get
like some free drinks out of it. Sometimes you're like, oh,
that your fiance's You guys are engaged. Congratulations first rounds
on us. When we checked into the hotel. Um. I
can't remember what the guy was saying, but he was like, uh,
(33:01):
he's like he didn't even ask if we were celebrating
a special occasion. But I made sure to let him
know that we just got engaged like two days before,
like praying he would upgrade us to like the honeymoon
suite or something like that didn't work. And he didn't
give it. He didn't give a single funck bastard. He
gave us a free He did give us a free
bottle of house champagne, which was very nice. Hey, there
we go. He probably does that to everybody. Um, but
(33:22):
that doesn't matter. You keep using that fiance. I guarantee
one of these days will pay off. Yeah. Um, wait
till you guys are married and you say your new
luwits you're gonna get everything free, And then what do
you do after that? Then you just say we allays
had a kid and then you get everything for free.
Um yeah, but then you start like not sleeping and
(33:44):
then in constant state of anxiety and stress. So you're like, oh,
it's cool that we got things for free, but now
it's not cool. Now it's not cool. Yeah, but you've
got a cute little baby to show for us. I
know he's the best, and uh he's dressing up for
Halloween right now, so he Um, it's pretty cool. He's awesome.
But Dean, congratulations, man, So exciting for you and Klin.
(34:06):
You and Klin definitely has to come on this podcast
talk about her side of the story, because I have
a feeling it's going to be wildly different. Yeah, I mean,
it'll probably be a lot more realistic. Yeah, you know,
I know, but I'm I'm excited to hear that tale. Yeah, she'll, she'll,
she'll do it. Um, I didn't want to have her
to come on this episode. I wanted it. Uh, maybe
(34:29):
we'll have her in on like the next couple of
weeks or something like that. But but yeah, she well,
so she's supposed to propose to me now too. Oh yeah,
I forgot about that. That was the deal that we
would propose to each other. Is that still planned? I
think so. She she said, my ring isn't ready yet,
but she was so certain that she was going to
propose to me before I proposed to her. Obviously that
(34:51):
didn't happen because I've already proposed to her. But she's
said before the end of the year, so she's only
got two months, two months and a week left. Um,
but we'll see how that goes. I guess that's yeah,
I forgot about that. Yes, you guys have another proposal coming.
I wonder where she's gonna do it. I don't necessarily
need one at this point. She's it was just basically
(35:11):
steal my thunder from me for proposing to her. Yeah,
that would be a selfish move. That would be a
selfish move. I didn't realize how much power is bestowed
upon you by being the one to propose. Yeah, you
know what I mean? Like you like like now, Kalin
(35:31):
can't get angry at me, or actually couldn't get angry
at you because you're like, well, I just asked you
to marry me and you said yes, So like what
is there to be upset about? Like not like and
I'm talking like just like an everyday things like oh
I didn't clean my dishes, Well, too bad, because I've
already asked you to marry me and you're marrying me. Yeah,
you signed up for this, You signed on for this. Yeah,
so who knows. But we go to Galapagos tomorrow, oh
(35:54):
today actually, and maybe she'll do it there. You guys
don't stop. Well, we'll be on the lookout for another
agement for Dean and Kaylin. Also a quick shout out
to grocery store Joe and Serena, who officially got married
the same day, which was crazy the same day you
guys announced at least um so crazy. It just shows
that paradise rules them. All, um, so quick, congratulations to
(36:16):
two wonderful people, Joe and Serena. Wish you nothing, but
what about what about the confirmed news today? It's just
so frustrating and so maddening, and like people it's people
wonder like what's going on with Tom? What's going on
with Tom? It's like, really, you have to ask why Tom.
Maybe he isn't playing to the highest level he's used to,
(36:38):
Like the dude didn't play. He played okay last night,
but it's like he knew he was signing the papers
this morning. How could you even think about football last night?
So it sucks. I'm I have a lot of strong
feelings about this. Uh that will dive into on a
separate episode because we're leaving off on a happy note here,
not an angry note. Um, but uh, you know, as always,
(37:03):
I'm team Tom. I just don't understand if one one
last parting piece of wisdom here, if the two most
beautiful people in the world, the two most successful people
in the world, can't make it work, how is there
supposed to be any help for the rest of us. Yeah,
love is dead. Love is dead. There's no hope for
any of us. But you know, hey, whatever congratulations on
getting engaged. You know that's cool. Whatever, Thanks anytime. We'll
(37:30):
make sure you guys tune in next week with this
episode is coming out Sunday. Sunday everyone, Happy football Day. Uh.
And then Tuesday we also have our episode with Olivia
Creedy which is coming out. And then Thursday, of course
we have our Caller episode as well, so tune in
for those and make sure you tune in next week.
We're hopefully we all suck a little less. Dean sucks
a little less now for now, follow help by Suck
(37:51):
at Dating on I Heart Radio or wherever you listen
to podcast
Popular Podcasts
True Crime Tonight
If you eat, sleep, and breathe true crime, TRUE CRIME TONIGHT is serving up your nightly fix. Five nights a week, KT STUDIOS & iHEART RADIO invite listeners to pull up a seat for an unfiltered look at the biggest cases making headlines, celebrity scandals, and the trials everyone is watching. With a mix of expert analysis, hot takes, and listener call-ins, TRUE CRIME TONIGHT goes beyond the headlines to uncover the twists, turns, and unanswered questions that keep us all obsessed—because, at TRUE CRIME TONIGHT, there’s a seat for everyone. Whether breaking down crime scene forensics, scrutinizing serial killers, or debating the most binge-worthy true crime docs, True Crime Tonight is the fresh, fast-paced, and slightly addictive home for true crime lovers.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
24/7 News: The Latest
The latest news in 4 minutes updated every hour, every day.