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November 29, 2022 27 mins

Ashley sits down with a newly engaged Caelynn Miller-Keyes for an IN DEPTH conversation about her relationship with Dean, their future together, and how exactly he proposed when he lost the ring! 

Caelynn doesn't sugarcoat anything when she tells us about her miles-long engagement hike and why her interest in crime might become your new favorite podcast. 

See omnystudio.com/listener for privacy information.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
This is Ben and Ashley I Almost Famous in Depth.
Hello everyone, welcome to the Almost Famous podcast. It's Ashley
and I am the solo host today with my guests
Kaylin Miller Keys Welcome. Thanks for being here always. You're
such a good constant in our lives. Well, thanks for

(00:22):
having me. Well, we haven't talked to you since you
and Dean got engaged. I know that you've given specifics
of the engagement on Dean and Jared's podcast Help I
Suck a Dating just to ironic that the two of
them are now in very committed relationships, but they still
suck a dating. And let me tell you, Jared does
suck a dating because we barely go on dates and he's, Um,

(00:46):
I don't remember the last time he did anything romantic
for me. Now I'm gonna this is how I'm starting
it off. Um, he used to be so romantic and
that's how, like I guess, life goes. But how has
Dean been romantically since you guys got together to now?

(01:07):
Had there been any has has there been any shifts?
Has he been romantic? Yeah? I think he's more romantic
than me. Um, which I wasn't expecting. But I'm sorry
if you can hear that. That's his motorcycle he's taking off.
Uh he Yeah. The start of the relationship, I feel
like I was like more, not more into it, but

(01:29):
like more romantic. I guess it's just the best way
to put it. And then slowly he became more open
and more vulnerable with his feelings and everything, and now
he's suddenly the more romantic one. Oh that's so cute.
What was the last romantic thing he did besides proposed
to you, because we'll get into that very soon. The
last romantic thing, well, at Thanksgiving we did like what

(01:51):
are you thinkful for? And then you just said the
sweet thing about how he is excited to marry me
and spend the rest of my life, spend of the
rest of his life with me. So that was sweet.
I don't know, like romantic gesture wise, When he's done,
then yeah, see Jared says romantic thing. He says like
kind loving things like that all the time. He's really
good with words of affirmation. But like, I'm like, almost

(02:11):
the last time you just did something because you know,
just surprising with flowers, I don't know, I know Dean
does not understand flowers, and I think he's gotten me
flowers once in three and a half years. They're so nice.
What would you what would be your ideal like romantic
gesture gift from him? Um, Actually, he just bought me

(02:35):
this five ft tall gnome, which I'm like obsessed with
holiday gnomes, so I'm looking at it right now. He
like he does little things like that where he'll surprise
me with gifts. But I don't think he likes flowers,
like flowers will be nice to come home to every
once in a while. I get. I get how guys
think about flowers though, you know, they think they die,
and you know, what's the point. I think the gnome

(02:57):
is actually way more romantic because it's very personal five ft.
I just let if that's romantic, then my gesture was
romantic as well. We were at home depot looking for
fake Christmas trees and Jared saw a nine foot grinch,
a blow up one. And he has this thing where

(03:17):
he loves cheesy holiday decor for outside. It's like that's
what his dad was into, like plastic things and blow
up things. And I'm like, this is so embarrassing. No,
but this was so like I'm still like a reverence
that I was just like, okay, yeah you you, I
see you eye belong that get it, satisfy your little

(03:39):
your Christmas elf self and and do it. So I'm
sure it'll be blown up in the front yard later
this week. I'll get a good laugh out of it. Anyway,
we could talk more about this later when we're talking
about holiday traditions, because we're gonna do a little bonus
podcast about our holiday traditions and favorite things. So right now,

(04:02):
I wanted to dig a little bit deeper and of
course into the engagement. So my thought is that you guys,
it's like, wasn't a surprise to you at all? Am
I wrong? Um? It was. I always thought he was
proposing in quiet and then he lost the engagement ring,
so then I was like, I guess he's not proposing.

(04:24):
But I knew he was going to propose by the
end of the year, but losing the ring really threw
me off. So you thought he was gonna wait until
he found the ring or got a new one. Yeah,
I thought he would wait until he found it. But
like you guys, knew that you were going to get engaged,
and like you knew there were what there was going
to be a proposal because you even went and picked
out your ring. Yeah. Yeah, I mean it's been sitting

(04:48):
in our drawer for like four or five months and
you've known this Yeah yeah. Did you look at it
in the dour Yeah? I have like photos of it
on my hand. I would try it on all the time,
and it's obviously not been lost. Now for those who
are wondering, what is this about a lost ring, well,

(05:09):
Dean actually lost the engagement ring that he was in
the first place resistant to get for Kaylin because he
didn't want to spend money on a ring. You know,
Dean a little a little hippie dippy kind of thought
that it was superficial and not worth not worth it,
you know, but you really wanted the ring that you wanted,

(05:30):
and he ended up I don't want to say caving,
but seeing your side, yes, seeing my guess, seeing my side.
We had so many conversations about it. He doesn't understand
and now, like in the wedding plan aspect, he just
doesn't understand how things can cost so much. So he's like,
how could a ring cost so much? And now that
we're wedding planning, he's like, how could a wedding cost
so much. So it just about like using him into

(05:52):
things and like starting small and then getting a little bigger.
Was there anything about you guys splitting the costs of
the ring? I just wanted to buy it because I
knew he didn't want to buy it, And I was like,
there's a ring that I want, and I and the
breadwinner in the relationships, so why shouldn't I And I'm
wearing the ring every day of my life. So I

(06:13):
was like, I don't think it's right that you should
pay for it. And then we came to the compromise
that I would buy him a track and he would
buy me engagement ring. That's sweet. Were they on par? Price? Was? Yeah,
well I put down a down payment and then yeah,
he's paying off theirs. That's so nice. So the ring
you had been eyeing for a while, when did you

(06:36):
actually say like, okay, let's get it. Um he came
home one day, Yeah, he I found the ring and
then it was purchased by a jeweler and they were like,
all right, you just sent to pay for it. So
I sent him the link to pay for it, and
then he's like, no, I want to buy it from
somewhere else. I still to this day have no idea
where he got it from. So then the jeweler had

(06:58):
to return it back to where they purchase a step from,
and he bought it, and then we were on a trip.
I think his friend took him to the airport and
his friend was like holding onto it for like three
weeks or something. Did he have it when he climbed
Mount Everest? No, okay, no, because it was here because
because you're like, I tried it on during that trip. Yeah. Yeah,

(07:19):
I actually flew it to New York because I was
going to have my jeweler make it into a ring.
And I'm standing in front of the door and Dean's like, no,
it's my meetings at nine am. It's eight fifty nine.
And I was like, all right, I'm about to drop
it off and he's like, no, take it back, like
I want to make it. So like it was literally
about to be it's still just a loose stone wherever
it is. It was about to be made into a ring.
And then oh wait, how how did you put a

(07:41):
loose stone on your finger? I was just like rest it, okay,
so you found the stone that you really liked, and
then the jeweler was going to put the stone on
the setting, but he was insisted on one particular or Julia.
Was he going to get a little bargain. No, I

(08:03):
don't know who it was. I don't think he was
going to get any sort of discount. Also, like we
had been talking about this for months. I was like,
I'm going to New York. I'm going to drop the
ring off. We have been talking about this so much.
And then once I'm there, I like flew it safely
to New York with me. I was stressed about it
the whole time. He's like, never mind, I want to
make it, Like, how do you just We've been talking

(08:24):
about this for so long, But that's kind of on
part for him. So he wanted to have something to
do with the design. Did you have the design laid
out exactly how you wanted it? Very particular? Okay, yeah,
But then I was excited about that. I was like,
it's super sweet that you want to do it, and
I think it's more romantic now, right, Surprised when I

(08:44):
see it for the first year, Right, So I get that,
Like that seems like a like I like that that
there's some sort of surprise component to the proposal. But
then but then he goes and he loses the ring.
Why wasn't in a drunk drawer in the kitchen just
a loose stone, I'm told I'm told via my husband
that it was a loose stone wrapped in a napkin

(09:08):
in the kitchen drunk drawer. Why wasn't this one at
least in a little jewelry case, let alone like in
a safe and some something. Well, that's why I'm confused
where he bought it from, because that's how he purchased it.
It was just wrapped in blue tissue paper and still
as long as it's not in the garbage somewhere, it's
still wrapped in loose tissue paper somewhere. But I guess

(09:31):
he came home and it was just sitting on the counter.
So I just put it in the drawer and it
sat there for months, and then I was checking in
on it periodically. I would like go to try it on,
and then I kept hinting like, if you're going to
propose by the end of the year, this takes a while,
you should probably go get it made into a ring.
And he asked me to stop pressure him to get

(09:51):
it made into a ring. So I stopped asking, and
I would still check in on it periodically. I checked
one day and it was gone, so I was like, okay,
he took it to the jeweler. Um turns out that
that is when it went missing, because the next day
he was going to go take it and he was
then confused where it was. Kaylin, I can't get over this.

(10:12):
And now I'm even more mind boggled as to how
this is all happened, because my theory was that you
didn't know it was in that drawer, and you saw
like paper or something in the drawer and you're trying
to like clean up, and then you just toss it out.
How did it actually just disappear? It's so weird, and

(10:34):
we spent hours and hours. We have a camera at
that points directly like in their kitchen, has a perfect
view of it. We spent hours going through the footage
and trying to figure out when he took it, because
I wouldn't take it. It's not I have nowhere to
put it and nothing to do with it. If I did,
I would put it right back. And we cannot find
when he moved it, So I don't know. I'm not

(10:54):
even sure that ring I guess like ring insurance is
not even a thing because it wasn't a real ring
yet you wouldn't have had it ensured, so you just
like thousands of dollars down the toilet. Yeah, and he's
been spending all day today working on his motorcycle and like,
why aren't you searching for the spring? He is so
nonchalant about it. I'm like, I don't think he cares

(11:15):
that it's gone. This is because he doesn't value money. Yes, seriously,
this would frustrate me to no end if I lose, like,
let's just say a set of like hundred dollar headphones,
I'll go crazy, you know, like I will always scour
my brain, like right now, there's one thing in this

(11:36):
house that oh, yes, okay, so there's a camera, baby camera.
And when we moved, I thought that the baby camera
was in a like you know, one of the storage
bins in the basement. So I was like, oh, no problem,
when I need that when his crib goes upstairs, I'll
just go scour those bins. And now I can't find
them at all. And I think about it almost daily.
And it's like a two camera, let alone a gem stone. Yeah, yeah,

(12:04):
that's how I am too, and that's how most people are.
But so how I like, did you guys get angry
and did you get a fight about this? Because I
would have gotten Yeah, it would have been raging. I'm
trying to be very cool about this. I tend to
really stress and like, I, yeah, we can get in
fights over my stress. And I've really tried to just

(12:25):
be very calm throughout this whole situation. So far, I
have been. But I'm losing patients just because it's not
even like I'm happy with the ring that he got
his replacement ring, but I'm like, how do you lose
that much money? I'm just confused. All right, Well, let's

(12:51):
get let's try to get past the fact that the
ring is the stone is missing and get to the engagement.
So you you would initially that if the ring were
a thing, that the engagement, like the actual getting down
on one knee, would be in Kauai, a part of Hawaii. Um,
did you expect it to be when it was after

(13:14):
a hike of the century, The hike of the century,
like literally one of hike that people have died on
that experienced hikers have died on. Um, there's apparently a
very narrow pathway between like the edge of the mountain
and like the ocean. Right, yeah, so explain that whole

(13:38):
day to me. Um, yeah, I gosh it was. It
ended up being a great day, but like leading up
to it, it was miserable. I was miserable, and a
week before I started googling like what should I pack,
what should I bring? What should I know? And that
is when I started to freak out because people are like,
this is not for office hikers. And I have hiped,

(14:02):
but I don't enjoy hiking. I'm not in hiking shape. Um.
It's just like a specific type of shape that you
need to be in that I am not in. And
I'm very clumsy, Like i feel like my center of
gravity is off, so I'm always like tripping, Oh my gosh.
And there's like no railing nothing, there's nothing. It's just
like a drop off and if you fall, you die.

(14:25):
Did you hug like the mountain the entire time? Just
hand palms on the mountain during that section, That's exactly
how it was. I was like hugging the wall and
bring across. Um. Yeah, it was terrible, And I was
really mean to Dean right before he proposed, and I
told him I would never hike with him again for

(14:45):
the rest of our lives. Um. I just kept asking,
and I was like, how could you do this to me?
I'm looking back on it, I'm like, I was so dramatic,
but I really thought I couldn't do it and I
could potentially die. How Like, Okay, so you were mad
because once you got to that spot, the spot that
he actually got down on one knee, is like the

(15:05):
end of the hike, right, and it's like the final
destination that everybody loves to go and see. So you
had finished half the hike because you got there, and
then you still had to go back where you mad
at him because you really thought that you were in
danger on it. Um, yeah, we were. We were still
lit about two miles from the beach, I think two

(15:26):
or three miles, and so the whole time, I was thinking,
if I can't even do this now, like I then
have to hike out tomorrow, how am I going to
do this again? And so that's when I started to panic.
I was like, maybe I can do this once, but
I can't do it twice. That's where a lot of
the anchor came from. Okay, so it's twenty two mile
hike right, eleven miles to the beach and eleven miles
back and it's the same trail. Yeah, you do have

(15:50):
to do it exactly all over again. Yes, How it's
interesting that you say that you're not a hiker, you're
not a fan of hiking, because I feel like that's
all Dean has you do on vacation, I know, And
all I want to do is like tan or shop
or just like lounge around. And he everywhere we go

(16:12):
we either have to be rock climbing or hiking. Do
you guys compromise on that? Yeah? I feel like we
hike maybe once every trip, and then we do everything
and I want to do for the rest of the tether.
All right, well that's good. Okay. So he gets down
on one knee by doing something really cool. Can you
explain how he got it all on camera? Yes? So

(16:33):
he set up his tripod and we always take That's
the only way we get photos together is if we
set it up on our tripod and just have an
auto shoot. So that wasn't like I wasn't suspecting anything. Um,
and then he walks over and we're like taking photos
and kissing and doing like how we normally take photos,
very romantic, and then he was like I saw this
TikTok because he was filming on his phone too, and

(16:54):
he was like, let's stand back to back and then
we'll spin and face each other. So we did that
two or three times, and then he pulled out the
ring and got down a winning He pulled out the ring.
Oh yeah, he gotta he got it's not. The day
before we left, he went to a jeweler and then

(17:14):
picked this one up. Oh that's so cute. So you
do have something. Oh I love that. Oh yeah that's
so cool. Like this is fine, Like I don't care,
but I just can't believe that much money is lost.
You'll get it, You'll you'll find a way. I'm surprised
that are there are there jewelers that have reached out

(17:36):
and said that they'd like to do an exchange for
you on social media for a new ring. No, none, really,
after all these stories, I think that somebody would have
dollar signs in their eyes. Someone please, But I think so.
I'm just I'm gonna get a moisten that ring. And
is that the lab grown? Yeah? Yeah, yeah, yeah, yeah,

(17:59):
that just seems like a great option these days, I know.
And I wish I knew that before him, because I
never would have Boughtenden that truck because seriously, the Moist
Night ring I think is in the same carrot that
he got is about two or three grand. Really, yeah,
and it looks the same. There's gonna be I'm going

(18:20):
to say that, like engagements going forward, they're gonna have
to be like at least those. I know that, like
it's on a totally new thing, but I've been hearing
about it so much lately. And these rings are They're
gorgeous there. They are diamonds, They're just not mind diamonds,
which is great for you know the fact that a

(18:41):
lot of diamonds we don't know how they got on
our fenkers, you know what I mean? Right right for sure?
And I wish I would have known this before too,
because everyone talks about how expensive wedding planning is and
like weddings aren't general And now I spent that much
money on a truck, which I could have put towards
a wedding. But it's okay. Yeah, Well I'm sure he
loves his truck. He does. You guys are going to

(19:03):
change your last name when you do get married to Bell,
which is Dean's mom's last name. How did you come
up with that idea? Dean came up with it I
think a year a year or two ago. We were
with his family, and I think he mentioned it to
me first, and then he brought it up to his
brother he was about to get married. His brother loved

(19:23):
the idea. Send out their bells. His other brother got
married this past summer and they're also bills. So we're
the last ones. No way, that's so cool. That's really sweet.
That's a really sweet dedication to his mom um. So
you have obviously started wedding planning because you've been talking
about how expensive it is, and it is. It's very

(19:44):
very expensive. It's crazy, and it's the little things that
little details that will get you. Like audio, if you like,
choose a wedding venue that's not an act like your
traditional wedding venue, you'll need to pay for audio, You'll
need to pay for lighting, all these things that you
don't really think and those are like in the thousands.
It's so crazy. So what are you guys planning? Like

(20:06):
what kind of wedding? I can only imagine Dean getting
married outside. Yeah, yeah, it'll be outside in aspen Um,
which is he decided he wanted to get married and
asked when we were going to Elope in Italy. But
then he decided, we want our I guess we came
to the decision together. We want all our friends there.
But askedmen, it's like one of the most expensive places

(20:28):
to have a wedding. I've heard. Yeah, I don't know.
It's so stressful. And there's one point. I started getting
quotes because everyone talks about it, but there's no real
transparency with it. They just say it's expensive and that's it.
And so then I started getting getting hit with numbers
and I got really overwhelmed, and then I decided I
didn't want to get married anymore. But so wait, why

(20:53):
not a little like you just said when you got
hit with numbers, you didn't want to Elope, Why can't
you do something like with a small amount of friends Antelope, Like,
I feel like an elopement can also be like a
mini wedding. Yeah. The problem is we're planning our engagement
party right now. In that I booked the venue. The

(21:15):
max is forty people, and already I'm like, we're going
to hurt so many people's sayings yes for the engagement party,
and that's because Dean has eighty friends that he needs
to invite, So I don't know, it's stressful. He is
a social butterfly. It is really hard and somebody's feelings
always get hurt when it comes to weddings, whether it's
bridesmaid selection or just the invites. Right, you guys had

(21:50):
like these rumors surrounding you that you had a wedding
in Europe years ago, or like some form of commitment ceremony.
Is that true, because now that the engagement has just
been such a big thing, it feels like you guys
really weren't married. No, we never were. He just likes

(22:12):
to say things and stir the pot. He got you
along with it too. You were all coy, I know,
because I never wanted to ruin his little thing. So
I was always like, yeah, maybe you guys are really
good actors. I was convinced. I was like, yeah, I
think they're married. It's just not legal. It's like a

(22:32):
committed thing, you know, like they're together for life. And
there was like some shaman situation in would never do that.
It's going to be hard to get him to show
up to the wedding. He would never do like a
commitment ceremony, He wouldn't. I don't think so. I could
never see him doing that. But I can't see him
signing legal documents, you know. But what's great is that

(22:53):
he has two older brothers and an older sister. Everyone's
married except for him. So like once he sees his
older siblings is doing things, then he's like, okay, I
could do it too. All right, Well, before we let
you go, we have got to talk about your new podcast.
So you love crime, So you have a new podcast
with my Heart Radio. It's called True Crime Reality, in

(23:17):
which you interview reality stars about crimes that they've gone through.
I was able to listen to the first episode, like
in person, when Ben Higgins discussed his hilarious encounter with
cocaine um in Miami as a teenager, and it's all
caught on like the show Cops or is it Cops

(23:38):
and something like that, and he has the most like
non Ben Higgins sign off. You have to listen just
for the quote that you can somehow find on the
internet out there of Ben Higgens Ben Higgins saying something
that is so not Ben Higgins. But anyway, Kalen, it's
your podcast, explain how handled and some of your special

(24:02):
guests so far. Yeah. So Ben Higgins was the very
first guest, and it couldn't have been better because, like
Ashley said, it was just such a non Ben's story. Um.
And so there are like some funny crime stories, but
then there are also serious stories. Um, we covered a murder,
and we this week we covered Graham Bund came on

(24:24):
and we talked about the Vegas shooting. So yeah, it's
like lighthearted sometimes and heavier other times. And I think
this week was amazing. This is the first time Graham
has ever talked about being in the Vegas shooting. He
was on stage when it happened and on stage, Yeah,
he was like side stage, so he was on stage

(24:44):
but standing just to the side when it all started,
and he just like really went into detail, talked about
how he escaped and then he came back to try
and find his friend and really really really heartbreaking. Um.
And It's it's been interesting to just talk to so
many different people. I also talked to um Tara Newell

(25:04):
from Dirty John, who spoiler murdered Dirty John. So they're
just some crazy story podcasts. Oh he didn't. Yeah, And
I had just watched you know the you know, the
docuseries Dirty John. I was like a little stars back Brier.
I was like, oh my god, this is the same
girl with the same the voice. You know, it's crazy. Well,

(25:27):
speaking of wedding planning, I have a great place to
suggest for you, Kalin, or anyone planning a wedding. It's
tarrant Aa. We love Tarrania. Jared and I have stayed
there before. It's um a luxurious ocean front destination located
on a hundred and two acres of Palos Verdes Peninsula,

(25:49):
just south of Los Angeles. There is panoramic views of
the Pacific Ocean and Catalina Island. You can actually see
It's it's pretty amazing. Um. They have spacious, comfortable accommodations,
including over three guest rooms, thirty one sweets UM ocean
view rooms, twenty bungalows sorry two villas UM. And they

(26:11):
also have an award winning golf course, a full service spa,
and UM an amazing wedding and event space. So hey,
when it comes to wedding planning, put Tarana on your list.
Calin Alright, Well, Caitlin, you are rocking that as host,
and I want everybody to go check it out. It's

(26:31):
true crime reality and you can get it wherever you
get your podcasts. Calin, thank you so much for joining
us and giving us all those details. Yes, thank you.
All right, we'll see you soon. I guess we'll sign
off the way that I were supposed to sign off.
Are you ready? Remember how we do it? Until next time.
I've been Ashley. I've been follow the Benn and Ashley

(26:56):
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