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September 13, 2021 48 mins

Dean sets the record straight on his marriage and reveals a shocking discovery about Caelynn since they’ve been overseas. 


Jared and Dean answer all your questions in a raw unfiltered Q&A! And because it’s late at night where Dean is… his answers are spicy!


Plus, Jared shares what scares him most about becoming a father.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hell I Suck at Dating with Dengler and Dared Haben
I heart radio podcast. Hey, welcome to help I Suck
at Dating. I am Jared, have been and I'm actually
currently in a hotel in New Jersey right now. I'm
visiting Ashley's year old grandmother, God bless her. Uh. Dean

(00:23):
is going to join us in a few minutes. I
think he's having internet troubles right now. He's still in
Europe traveling the world with his beautiful girlfriend. And if
you follow Diana and Caitlin, they've actually been posting some
pretty awesome stuff. I'm pretty jealous. I have some serious fomo,
so I'm glad you're enjoying it over there. Hopefully his
internet connection will be okay and he'll join here in

(00:44):
just a few minutes. But we do have some hot
topics to talk about, specifically about a topic that Hannah,
our producer, is very invested in, and I want her
to join me on this conversation. Hannah, first of all,
how are you? And I was gonna attempt to pronounce
your name, I'm going to butcher it, but Hannah, Nuke
and Bomber, Okay, you were close? Are you saying naer

(01:08):
nuke a bauer Okay, and that's and that's German. Yep,
it's German. No one ever gets it right, so don't
even worry about it. So when you go on dates,
is this like a hot topic when people like, how
do you say your last name? Oh? What is it?
You know? Are you German? Is it a conversation starter
for you sometimes? But fun fact, I've never actually been
on a date because I've only been dating my first boyfriend. Like,

(01:32):
I've never dated in my life. You've never dated in
your life? How long have you guys been together? Over
four years? Wait? How old are you? Hannah? I just
turned twenty two. Okay, so you've been together since you
were eighteen? Yes, so it wasn't a high school romance.
It was after high school. Yeah, I met him on
my first day of college. Actually, usually that's the complete opposite.

(01:54):
Usually you have a high school romance and then you
go to college and then you guys break up totally.
I know it's backwards. Wait, so did you go to
college thinking like, Oh, I'm gonna go I'm gonna date guys,
I'm gonna meet people, it's gonna be a lot of fun.
And then day one you meet your potential future husband. No,
I didn't actually want a relationship at all. I was
very anti and it just happened. Well, that's amazing. Well,

(02:16):
it looks like Dean's in the waiting room too, so
he's going to join us right now. That's pretty awesome.
So you've never so you've been on a first date
obviously because you went on a first date with your
new boyfriend. Yeah. I think it's just different because we
started dating in college, so when we were hanging out,
it was at like parties and it wasn't a super

(02:37):
official first state, but we definitely had like a first dinner.
I wish you was on because I'm curious what he
thinks your first date was compared to what you think
your first date was. But that's a good question. I'll
have to ask him that later. What do you think
your first date was? Like? Is it the first time
that you guys kind of hung out or is it

(02:57):
like an official Hey, let's get dinner and that's the
first day. Well, the first time we hung out actually
was on my birthday four years ago, September four, and
I went over to his apartment. We just talked forever,
but then we The first time we got dinner was
at just this on campus food place, so technically maybe
that's our first date. He took me to dinner, but

(03:19):
it was so cute. It was just super casual. Sometimes
the casual makes the best first date totally. First of all,
happy belated birthday. By the way, Stem four just past.
Thank you. Did you do anything fun or you, guys,
because you're in l A so it's still a little
bit quarantinely over there. Yeah, we just hung out and
went to the beach, got dinner. Oh nice. So now

(03:43):
you guys can say you went on your first date.
You finally got dinner together, totally, And so I wanted
to bring you in because this is a topic that
you said you are very invested in, and it's about
Scott Disick and listen, I love Lord Dissack. I've become
a fan of keeping up with the Kardashians through my
wife Ashley, who obviously is a huge Kardashian fan. I've

(04:05):
seen episodes. I never really sat down and watched it,
but I have a certain level of respect for all
the Kardashians, their business savvy nous uh and I also
have always loved Scott dis sick, but apparently he's calling
out his ex Courtney Kardashian uh in a private d
M that got exposed to the public. So Unice apparently

(04:25):
leaked a d M from Scott Disac calling out Courtney
Karadashian and Travis Scott kissing having full on p d
A in Italy. So Unice shared this d M that
says from Scott Discac supposedly, yo is this chick okay?
Explanation point question mark question mark qush mark bro Like,

(04:46):
what is this in the middle of Italy, to which
Unite apparently responded, doesn't matter to me as long as
she happy. Ps, I ain't your bro. So apparently Scott
Discac is mad that Courty Kardashian in is having full
on p d A with her now boyfriend Travis Scott
in Italy. So what do you think about this, Hannah?

(05:07):
Why are you so invested in this story? Well? I
just think it's interesting because Courtney's two ex boyfriends are
talking about her in a d M and it gets leaked.
Like if I had two ex boyfriends in the Scott
leaked I would feel so strange about it. Yeah, it's weird.
Why would Scott disn't care so much, right, and it's
you jealous? Kind of seems like it. I think he's

(05:30):
definitely jealous. Dean. Hello, Hey, guys, can you hear me? Yeah,
you're joining in the middle of podcast. I'm sorry, buddy,
what do you mean the middle of the podcast? I'm
three minutes late. You guys started without me that early.
You're fifteen minutes late. Oh my gosh. But yeah, I
thought the first I thought the first fifteen minutes were
like recording ad and everyone knew that I was already
gonna be a little late, so they really wanted me

(05:50):
to like join it like fifty five after the hour. Obviously,
lesson learned on my part. I apologize. We were at
a nice dinner and then I got to log on
my computer and I realized I left my microphone in
the car. No, how was your dinner? Oh my gosh,
it was a beautiful, wonderful dinner. How many more nights
you guys have there? Oh my gosh. Okay, So we
got into the Dolomites yesterday afternoon around like eight pm.

(06:13):
Dolomites in Italy are incredibly beautiful. Were in South Tyrol
right now, Sorry, I'm a little out of breath. I
literally was just sprinting to and from the car and
then parking lot because I forgot my freaking cord for
this microphone and I wanted to you know, if I'm
gonna be late, at least I can give the listeners
good audio quality out of this. So that's that's really
kind of where my head is at. I think you
sound great. Um, yes, it's because I sprinted it freaking

(06:35):
three miles to get the court. Anyways. Yeah, so we're
here for two nights. Wed we drive to another place
tomorrow night for two nights, and then we drive down
to Tuscany. And let me tell you this. We're driving
a lot around the Italian countryside and it is freaking
beautiful here. But one thing we like didn't overlook, but

(06:56):
we would may be like under emphasized, was that renting
a manual car, like a stick shift automobile. It's kind
of kind of bit us in the butt a little bit.
Kaitlin gets like the best part of the deal. She
doesn't know how to drive a stick so I'm stuck
driving us six hours a day. She's just sitting in
the passenger seat freaking playing a little crossroad puzzles damn

(07:18):
it out on Spotify, yelling at you anytime you get
too close to the curb. Yeah, oh my gosh. That
is one of the most stressing things. The front seat
driver where she's like, oh my gosh, watch out for
that car over there, and I'm like, yeah, hello, I'm
driving this car. Of course I see that car over
there as she shakes her finger. Ashley does the exact
same thing anytime a car comes into our lane anywhere nearest,

(07:40):
like literally within fifty feet. She's like, and I'm like, Ashley,
I got it, thank you, I appreciate it. And like
the thing is I kind of like get angry at
myself for like being upset about it, but at the
same time too, like I don't want to say it's
a manly thing, but it's like, hello, Like I'm obviously
driving this car. I I see everything that's going on,

(08:01):
not just in the hun eighty degrees in front of me,
but they also the hunter a reason behind me. I
know everything that's going on right now. And you're gonna
look up from your phone for two seconds and give
a little shriek because you think I'm doing something that's
a little dangerous. When in reality, it's not dangerous at all.
It's just it's there's no place. I mean again, it's
coming from a good place, but it's just like, just
let me do my thing. You're gonna get to where

(08:21):
you gotta get too safely. Don't worry about it. Yeah,
you have precious card now you're taking care of. So
I did want to go back to this article that
we were talking about. I don't want to bring Hanna
back in here too, because she's very invested in this topic.
So pretty much uh notes on this Dean is Scott
Disick who used to be married to Courtney kardashi and
they were not married, not married okay, sorry, thank you,

(08:44):
Hannah to feel free to correct me. And my wife
is yelling at me from the other room telling me
they weren't married Scott Disick and Courtney Kardashian. Hey, Caitlin
also yelled at you from across the room here that
they're not okay. So I just want to let you
know everyone's yelling at you that they're not marring. Okay, now,
I got it. Not married, not married. Everybody canna hear me?
They were not married, but they do have kids together.
Am I right on? That one okay, three kids together,
telling me okay, So Scott and Courtney have three kids together,

(09:06):
and she used to apparently date this other guy, Unice.
I don't know who he is, but apparently Scott d
m Unice with a picture of Courtney and Travis Scott,
her new boyfriend, making out in public and Italy and
their d m read yo is this chick? Okay? Bro? Like?
What is this in the middle of Italy, to which

(09:27):
Unice responded to Scott distick saying, doesn't matter to me
as long as she's happy. Ps I ain't your bro.
So Hannah is very invest into this because it's weird
that like two ex boyfriends of Courtney Kardashian are talking
about her, which is kind of weird. I don't know
why Scott disc would like d m Unice this, okay,

(09:47):
I um, I just gotta interjected. Hunter probably knows the
answer to this question. It's it's weird that they're d
ming each other. But how do we know that they
were demming each other? So Unice is the one who
screenshot at this because apparently Scott d m Unice another
ex boyfriend of Courtney, and said the message like, yo, bro,
what is this trying to make fun of Courtney and

(10:08):
Travis Scott making out in public and then Unite screenshot
at it and released it to the public. Supposedly this
is a allegedly Yeah, well, they're all right, they're all
looking for attention, which you fully understand. You gotta attention
pays the bills when you're when you're in their realm.
But it's still whenever someone um screenshots like a message,

(10:28):
like a like a string of messages and post them
all over Instagram, especially someone like that, you know, like
someone with a platform or whatever. I said, I pretty hard,
but I would love to hear Haunta's take on all this.
I mean, I just think Scots jobs. First of all,
I think it's Scott's definitely jealous Scott super geals. I
think it's a red flag that Unite posted it to

(10:50):
Instagram trying to come off as the nice guy because
I think he wanted to show off his response. We've
seen that before, haven't we did? Yeah? I mean, guilty,
guilty you Oh do you just assumes you know the whole,
the whole blake thing when he released the d M
s of Klin and I was messed up, right, right,

(11:12):
right right. Anyways, Hana, back to your back to your
side of everything. I mean, I just think it's so
interesting because then I think this caused some issues in
Scott Discac and Amelia Hamlin's relationship. So it's just such
a snowball effect and there's so much to uncover here.
And just to just to clarify, Amelia Hamlin is the
nineteen year old girl that he's dating, right, correct, but

(11:34):
they are no longer dating. They just recently, which we're
going to get to our next article, which all like
intertwines everything. Now, this is from e Amelia Hamlin sends
cryptic message amid Scott Disick turmoil with a quote never settled.
So Amelia Hamlin is twenty years old. She was dating
Scott Discac, who is thirty eight years old. She's the daughter.

(11:56):
What I know, they just broke up. So this is
what happens. See, this is exactly what was happening to
you in the car, Dean, where like Ashley barely hears
anything that we're talking about and immediately interjects with news
that I've already covered. It's the same thing. Klin, looking
at her phone, looks out for two seconds and tells
you something that you already know because you see the
car in the other lane. I digress. Uh. So Amelia

(12:18):
Hamlin and Scott disac have broken up. She was twenty,
he's thirty eight. There's a big age difference. Obviously. She
is the daughter of Lisa Renna, who is the you
know who this person is. She's an actress, she's on
Real Housewife, she's very famous. Uh. And so Amelia throughout
this entire drama posted a cryptic message on her Instagram

(12:39):
story that read, never settle for less, not with your job,
your friends, and especially not with your heart. Continue to
seek what you are looking for, and do not shrink
yourself for the sake of other people. You deserve the best.
So my question is, Hannah, you probably know best. Is
she talking about Scott Disac here? I mean, that's what
everybody thinks. That's I think it's just too much of

(13:02):
a coincidence for it not to be. And then they
break up. It's Scott. It's totally like, wasn't this whole
whole storyline? I'm keeping with the Kardashians that Chloe and
Kendall wanted to try to reignite things between Courtney and
Scott before the whole Travis thing happened. So, like, it's
clear that Scott is still wanting to be with Courtney.

(13:25):
Am I right? Totally? I think if he had it
his way, he would be back with Courtney two thousand percent,
and he's just jealous and wishes he was. So can
we get a little bit more context with their whole uh,
with Scott ian Courtney's breakup, and then also Scott and
Amelia's breakup? Like why was this most recent? I'm getting

(13:46):
I'm getting to the stink eye from Kitlin as if
I should know this totally, dude, My wife is yelling
at me in the other room. I know that Scott
and Corney be broken up for a long time, but
what's Scott's most recent breakup? What's the story behind that?
His most recent breakup before Elia? Like? Why are why
are him and Amelia broken up? I mean, I just well,
and then I do think their breakup may have something

(14:06):
to do with Lisa, her mom. I don't think she
really approved of the relationship, which I don't really think
my mom would approve if I was dating someone that
much older than me. But I think there were so
many different factors that went into this breakup, and the
whole Unice and Courtney Instagram situation was just one of
the factors. Yeah, Lisa called their relationship between her daughter

(14:29):
Amelia and Scott toxic, and she actually gave an awesome quote.
She said, quote, why can't it be Harry Styles? Why
the f is it's Scott Dissick, which I thought was
pretty good because obviously every mother wants their daughter to
date Harry Styles, right, but unfortunately Harry Styles is dating
Olivia Wildish also just sent out the other day, which

(14:49):
I also just find out Olivia munt and John Mulaney
are having a child together. A lot going on in
the whole celebrity world just does not stop and not
stop up in you know, that's what keeps our podcast going. Really,
I guess I don't understand why the whole I don't
under like Lisa Renna just now decides that it's inappropriate
for her young daughter to be dating this thirty year

(15:10):
old man. It's like, well, they've always had this huge
age gap, while all of a sudden thinks she's always
been against Scott Distick dating for her daughter. I mean,
what daughter would want to date? Like, what mom would
want her daughter to date Scott Disick with his background
probably not a lot. Yeah, I guess, I don't know. Yeah,
you're absolutely right. I just feel like Lisa Renna, I

(15:30):
know it is Kaylin's like favorite personality on Real Housewives
of Beverly Hills. I think it really and so so
she speaks highly over to the point where she like
is entertained by her thoroughly. Um, It's just yeah, I
don't know. I guess I don't want to overstep my
boundaries by saying anything wrong, but I feel like a
family like that kind of like is totally cool with

(15:54):
dating someone for the sake of like being in the
spotlight more or less, you know, and her daughter dating
Scott Disick death only like kind of gets people talking
about them a lot more. Which for someone like Lisa Renna,
who has been you know, famous for a long time,
is kind of like privy to and likes it and
wants it for herself, which I imagine she probably wants
for her kid too. It's just it's a little surprising

(16:15):
for her to say, like, I don't want you to
be dating this s guy, but you know, those people
even more interested than just her daughter dating Scott Distac
if she disapproves of it. Yeah, it's all a plan,
Like I think it's all. There's all a business side
to everything that these people do. I kind of respect it.
I'm not gonna lie. So I guess the question, Hannah,
this is what it really comes down to. And I

(16:35):
want to ask you, because you know the most about
this subject. Do we want Scott Disac and Courtney Kardashian
to get back together? I think so? They have three
kids together. I just don't know if they ever would
there's too much that has happened. But so you're not
you're not shipping Travis Scott in Courtney, Travis Barker, Travis Parker.

(16:55):
Who's Travis Scott? And why do I keep calling him?
Travis Scott? Is who Kylie Jenner just had a baby
with and they just announced that they're pregnant their second kid?
Got it? Yes? Okay makes sense now, So just to clarify, Hannah,
you don't want Courtney Kardashian to date machine Gun Kelly
because you think she could do way better machine Gun Kelly.

(17:16):
Was that a joke? Oh wait, Oh my gosh, I'm
so sorry. Okay, yes, these are all these answer blending
to making Fox bro I knew that I was just
that was that was deployed to take a little bit
of the stress off of Jared because he messed up
so royally, and that's it's It's definitely yeah. I want
to hear Han his final thoughts. What are they? I mean,

(17:36):
my final thoughts. I think why I'm so interested in
this topic is because Lisa Rennet obviously didn't approve of
a Melian Scott dating. And I don't know if I
could ever date someone that someone in my family didn't
approve of. That would just be a deal breaker for me.
But I guess Lisa got her way in the end
they broke up. I just would never be able to
be with someone that my mom disapproved of. No, I agree,

(17:58):
And that's why Scott just a ont to fit so
well into the Kardashians, because he gets well, he gets
along with with them so well. I hope Scott, Disick
and Courtney get back together too. I've always liked Scott.
I think he's crazy and over the top and obnoxious,
but there's something very endearing about that human being that
I appreciate, So I hope him and Courtney get back together.
Because he's definitely not over it. He wants to be

(18:20):
back with Courtney. That I believe. I will say too.
I feel like, because I think that both of you,
Bothna and Jared, you're very much like you would love
your family's approval for the person you're dating. Um, you know,
of course, you guys are very honored because they already
do approve of the person that you're with. I have
always said that, like, I don't need my family's approval,

(18:40):
but I will say my brother, like a year ago,
was like, hey, Dean, just by the way, Like it
was just me and him talking. He's like, just by
the way, Like I'm so proud of you finally like
knocking it out of the park with Kaylin or something
like that. And I was like, for someone that's never
claimed to need his family's approval to get his family's
approval meant a lot more to me than I thought
it would. And so I fully agree like if your

(19:02):
your family knows best in a lot of ways, like
if they don't think this person is right for you,
they're probably more right than you are because you've got
blinders on for whatever reason. So those are my final
thoughts on this topic. I wouldn't be surprised if we
see some more headlines regarding Scott and Amelia, and I
can't wait to discuss them with you guys, especially Hannah,
because you are so invested in this ongoing process with them.

(19:23):
But I guess we just kind of have to wait
and see. I know I would like to the podcast.
I apologize, guys. I'm just gonna go ahead and take
the initiative here and say we're gonna take a quick
break because I'm a little overworked and I think we
need to take a little bit of time off, so uh,
take a quick break. We'll jump right back into it
after this quick word from our sponsors. Oh my gosh,
I started. That was pretty good. Hey guys, it's Janna Kramer.

(19:54):
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(20:16):
your tickets today at on location live dot com. Let's
get lucky. Everybody, welcome back to help I suck at dating.
Jared is on Cloud nine, not just because he's recording
his favorite podcast ever, but also because his Tampa Bay Buccaneers,
which just sounds weird for me to even say one

(20:38):
the season open against Dallas Cowboys a few days ago,
and I just I think I can speak for everyone
when I say football is back and we are stoked.
There's no there's no reason for me to say these things.
I just wanted to say those things. So let's jump
into a Q and A segment. Let me just say,
it feels great to have Tom Brady back on my
television screen. God, I love that man. The thing is,
I just I couldn't go the whole episode without mentioning

(21:00):
something because I know you're excited, and I'm I'm excited.
To people who say you can't root for both the
Patriots and the Buccaneers, watch me. I've been doing it
for I say here already. You you're you're slowly bleeding
into not just being a Ton Brady fan, but to
being a full Tampa Bay Buccaneers fan. When you have
you have two Bucks jerseys. Now you've got a Brady jersey,

(21:22):
and you've got a ground jersey. Well, the Gronk jersey.
I was at a charity event for a silent auction,
and I always when it was for a golfing event,
so you can relate where you go to these golfing
tournaments and everything is free, and you're like, well, I'm
going to donate obviously because it goes to a good cause,
and they have these silent auctions. So I'm like, well,
I'm gonna donate. It's nice to do it for the
silent auction because then I get something really cool. And
they had this Cronk jersey and it was signed by

(21:45):
Gronk because they invited him there and you couldn't go,
and I was like, holy crap, that is so cool.
Like I've always said, I've only wanted to Tom Brady
Tampa Bay Buccaneers jersey because that's what I really ultimately
care about. But I was like, I do love Gronk.
This jersey is badass. So I ended up getting it,
and then I was like, all right, whatever, I mean,
I love Gronk too, And honestly, I was watching the game.
Long story short, I fully realized that I'm not a

(22:06):
Tampa Bay Buccaneers fan because like even like the stadium,
the flag, the emblem, I'm like, this is just it's
so like Tom Brady is so much better than this.
He deserves so much better. I'll give it one more
super Bowl until you're wearing the Rande Barber Jersey, Awark
Done Jersey and John Lynch Johnson Jersey. I talked about
how we wanted Super Bowl two to John Gruden, my hero.

(22:30):
You're gonna have a freaking James Winston Jersey while he's
still playing for the Sands, because that's how much of
a bucks. Anyways, all that aside, I'm sorry for the
tangent everyone. I know you guys don't care about our
football fandom. Let's get to the Q and A because, um,
I'm gonna be honest with you guys. It's currently ten
pm here in Italy. I've had a lot of glasses
of wine. I tend to put my foot in my

(22:50):
mouth when I drink some wine, especially, so let's ask
you some questions. Baby. The sooner we get to the
Q and A, the more likely Jared and I are
just say something. So I don't want to give d
any time to sober up, So let's do the first question.
So these were all asked on Instagram again, follow us
please on help I suck at dating. Uh. And then
we always post these type of things where we love
you guys engaging with us, asking us questions that really, uh, well,

(23:14):
you're just doing our work for us. Dean. First question,
what is the best place you have traveled to? Well, dude,
you so you've been to Positano before. I bet you.
Positano and Lake Como are pretty similar. Lake Como was
like pretty special, Like that's very, very beautiful out there.
And it's funny because a lot of the people that
ran into like we're just you know, Caitlin and I
are just a couple on vacation. They're like, oh, are
you guys like here for your wedding, for your honeymoon?

(23:37):
Like no, like we're just here because we've always wanted
to visit. And they're like, oh, you you got to
come back, like for your wedding. It's like what definitely
is like a place where a wedding would be spectacular.
It just is like one of the most beautiful places.
We were visited a little bias just because that was
like three days ago. So that's probably like front of Mines,
but the best place I've ever visited. Um, I mean,

(24:00):
I've always said Japan, and I probably will stick with
that for now until I go somewhere now. But what's
your favorite, Because you've been to quite a few places too.
I would say Capri, uh was stunning, But yeah, we've
been to Positano. I mean our honeymoon man was just spectacular.
One of the most breasthtaking places I've ever been doing
my entire life, and one of those times that you
just experienced if if you're lucky once and I feel

(24:22):
so lucky to been able to see it and go
on there for our honeymoon. So I'm curious, now that
you're in Italy and you're, you know, immersed in all
this romantic environment and culture, would you do you feel
more inclined to get married? Like, are you more open
to the idea of possibly getting married now that you
guys are kind of doing this extravagant adventure together. I Mean,

(24:45):
it's funny because it's definitely a comba. This trip is
a comba of like the things that she likes and
things that like I've never been to these places before,
minus the Dolomites, which I was with her originally, so
it's like we're experiencing a lot of this for the
first time together. Also, she is like in her comfort zone,
you great food, great wine, like beautiful little towns with
like cute little boutique stores. So it's like fun for

(25:07):
her in that sense, but also really fun for me
for experiencing it for the first time. And there's definitely
like a romantic aspect to be behind it a thousand percent.
You can't help but feel it, you know. Yeah, I
mean even in like we were so we started in
Santorini too, and even in Santorini, it's like you're in
these beautiful restaurants, like overlooking the coast, drinking wine, like
eating delicious food, and like you can't help but be like,

(25:29):
oh my gosh, this is amazing. I want this to
be the rest of my life. And since I'm here,
like I want you to be there in my life
for the rest of my life, which I had always
I'd always thought those things. Obviously, Caitlin is like fiss
pumping on the bed. Yeah, she's like, I freaking knew it.
I handcuffed him. Badda bang bada, boom, my job is done. Yeah, yeah, yeah,
she's trapped on the bed um. But the marriage thing,

(25:52):
I don't know, Like, yeah, I guess, I guess, but
I guess you guys are totally getting married. She's gonna win.
I mean, you'll be winning by marrying her, obviously, but
right she would be losing that one tenfold. We talked
about it too, she because we were like, if we
got married in Lake Como, obviously super major hypothetical. She's like,
would you who would you invite? Like who would you bring?

(26:13):
Blah blah blah, And it's like, I probably wouldn't bring anyone,
you know, like my family. Maybe that's it. You guys
have already talked about it, dude. That's why I was asking,
because I was figuring, if you guys are in this
beautiful setting, in this beautiful place, you've been together for
what two years now? Over two years, like I can't
many seven months, I cannot imagine the conversation hasn't come up.
And so I was prying a little bit, and I'm

(26:34):
glad I got an answer. Yeah, I mean, you can't
help it when you're in these places, you know, when
we're back home in Los Angeles to Las Vegas. Oh yeah,
we don't talk about it at all, but when you're
on the most romantic vacation in your life, yeah, it's
gonna come up every once in a while. It was
one of the reasons why I traveled all the way
down to um Oh where did I confess my feelings
to Ashley? The place is called Sugar Beach St. Bars, No,

(26:56):
not St. Bars uh. St. Lucia, Holy crap. That's why
I went down to St. Lucia because I knew when
Ashley was dating this other guy. I was like, it's
not going to be the same if we talk about
it at a cafe in Los Angeles, Like, I gotta
go down there in this beautiful scenic place and express
my feelings to her because it'll be so much more
of a moment than me doing it, you know, in Glendale.

(27:20):
So I totally agree, Like, when you guys talk about
it in like como, it has a certain more it's
more impactful than if you're talking about it at home. Yeah.
And in addition to that too, So I think we've
talked about in the podcast before. Kaitlin and I have
this pipe dream where we want to live abroad for
maybe like a year or two, and we've always known
Japan was an option. South America like six months in
each spot, and I think we've had Italy to the

(27:41):
list as well. And I'm not a big fan of
vacationing places and then deciding to live there because I
think you kind of like get the wrong perception of
those places. But man, Italy is just so freaking cool.
Italy is like one of the coolest countries ever. You
can get like a delicious spaghetti dinner, the best glass
of one you've ever had for like twelve buck like
every single day for the rest of your life, and

(28:02):
just like walk around these like beautiful cobblestone streets and
be perfectly happy with how everything is going. It just
is like one of those I don't know. Italy is
definitely one of those places where you can get like
like time just seeps away, you get sucked into it,
and then all of a sudden, it's like ten years
later and you're like, oh my gosh, I guess I'm
an Italian person now. Totally. I think it is the
second most beautiful place I've ever been. The first is

(28:24):
Rhode Island, of course. Uh So, the next question I
wanted to ask you before we ask me A question
is did Kalin love traveling as much as you did
when you first started dating or is this something that
has grown over time from being with you. Well, I
still don't think she enjoys as much as I do.
She claims too, and I think she does think that

(28:44):
she does. But she as much of a traveler as
she is. She's definitely a bit of a homebody. You know.
She loves her space, she loves her pride like privacy
and seclusion. She's an introvert, which is great. Um, and
she does love traveling, but uh, I mean I like
to think that I like it more and she probably
would beg the different too. She's actually shaking her head

(29:06):
on the bed right now, um, which is understandable. I
I think that I had the opportunity to travel a
lot more before we met. You know, you go on
the show, you start having the opportunity to make money
through like social media, and you don't have to work
your nine to five jobs. You have more time, you
have more money, Like, what are you gonna do with that?
You're gonna travel? Um? If you're if? You know, some

(29:27):
people don't, but like obviously like in my case, I
was like, I gotta travel, so I I had like
maybe like a year or two under my belt before
we even started dating, and she didn't have quite the
same amount of time. So she um loves it, no
questions asked. But I would always say that I like
it more. And like I said, I'm sure she would disagree.
I mean, you did live in a van and you
still do at times, so I'd argue you like traveling more.

(29:52):
I'm gonna, hey, I'm gonna find this Q and A
section real quick on my rundown and ask you some
questions here because I feel a little not blindsided, but
I feel like I'm an pplies in the conversation right now.
So Jared, I gotta ask, when it comes to being
a dad, what are you most terrified about? Um, I'm
most terrified. I think I'm most terrified of not living

(30:14):
up to expectations. Uh. My my dad is uh the greatest.
You know what he's done for me, for my sister,
from my mom. He's not perfect, but I mean the
level of sacrifice that he's given for us is I

(30:36):
mean no words for me, honestly, because the amount of
love that I feel from him and my mom too.
But if we're just speaking as like a dad to
dad type of thing. Now that I'm becoming a dad,
I think that's what I'm most nervous about, is that
will I be willing to make those type of sacrifices
that He's made for us for my future son. And
I think that makes me most nervous because now it's different.

(30:58):
You know, I care for Ashley a lot. I do
so much for her, but she does so much for
me as well, and she's a full grown adults, so
there's only so much that I do for her, you
know when you talking about a kid, you know, waking
up every hour on the hour, to make sure that
they're okay, make sure they're not crying in the early stages,
to see them grow, and make sure they're feeding. Like,
am I gonna, Like I'm nervous about you know what

(31:18):
if I get angry one day, you know, not that
anything would happen, but like, I don't ever want to
raise my voice or get frustrated with my son, and
I'm nervous about those moments. I think most of all.
Have you talked to your father about being a dad? Yeah,
a little bit. We had a really very special moment
when I first told him that Ashley was pregnant and

(31:40):
we had to go in the house for something, and
then he was walking out with me, and like I
could tell that he was kind of choked up a
little bit. He's such a softie, and he said, uh,
he's like, you know, I just know that the man
you are and who you've grown up to be and
me and he said, I know you're going to be
a great dad. And I said, thanks, Dad, So it
was really nice that you've given you any advice. Yeah,
I mean, I'm sure it'll happen obvious you like once

(32:00):
a little baby Dean pops out, but like anything you know,
broad Strokes purposes, Uh, Deanie Baby's Haven pops out in February. Um,
I'm sure he's going to give me a lot more
advice right now. It's more of he you know, he
just tries to help out. He always tells me, you know, hey,
if Ashley needs anything, you need anything, you just let

(32:21):
me know. I'll be there. But uh, no, like real
advice just yet. And I'm sure the thing is too
It's like, uh, I mean, I can't speak for your
own father, but I'm sure most parents would say, like
when they have their kids and they're in the same
boat as you, Like, they have no idea what the
heck they're doing, what's going on, what they're gonna be
like with what And then at the end of the
day too, it's like when you're when you're growing up,

(32:43):
like you think your father and your mom are like
the best people in the whole world. So it's like,
I think everyone kind of goes into it with the
mindset that they have no idea what they're doing, and
then they end up doing a great job because they
as long as they love them, you know, to the
best of their ability, that's the most important thing. I think.
So I agree, that's my advice to you, Jared. You know,
thanks and I appreciate. Alright, next question for you, Jared.
So you asked me tun or out, I'm gonna ask

(33:03):
you tune or out. So, yeah, they're like we said
at the top of this segment, there's no no question
that you're a big football fan. You lose to me
in fantasy football every single year. First of all, I
won the fantasy football league last year, which I was
so excited about. Hell yeah, dude, I had I played
Tanner and in the championship, and uh, I had Stefan
Daggs go on Monday Night Football and he went all

(33:24):
for three touchdowns on end up winning, and it was
that's gotta be so sad, especially being you, being Tanner
of all people, has to be the most satisfying. So
being as big with a fan of football specifically as
you are, are you gonna let a little baby Dean
play football when he's older than that if he wants to,
I'm in. I know a lot of people are nervous
about having their kids playing contact sports, specifically football and

(33:46):
all the CT and concussion uh information that has come
out over the past you know, however many years. But
the game is also safer now than it's ever been.
It's only gonna get safer because they want kids to
continue playing football, which means that they're gonna uh, they
want to reduce injury, reduce any type of brain injuries,
which has you know, plagued the game a little bit.

(34:08):
But I I would absolutely let him play. My goal
is for him to be a place kicker, because here's
the thing, dude. First of all, one of my favorite
Newing Patriots of all time is Adam veninary because as
a kicker, you have the opportunity to have the game
rest on your foot and that is so cool. So, like,
you are such a valuable part of the team. Don't

(34:29):
get me wrong, punters are a great part of the
team as well, But like there's no like huge pressure punt,
but there are pressure kicks, and I want my son
to have those pressure kicks. Plus, as a kicker, you know,
you have a long career, you don't get hit. It's
a really good gig. So that's my goal. I want
my kid to be a kicker in the NFL. I
gotta say that. On the flip side of that, you

(34:50):
look at someone like Cody Parky, you know you have
a couple of misses, your career can tail has been
real quickly. I mean, if he double donks like Cody Parker,
I'm gonna this own the kid right right right. I mean, hey,
I I'm kind of in the same boat as you.
If I ever had a kid, um, I don't know
if I would like ever push him away from playing football,
but I don't think I'd have an issue with it.

(35:12):
So I mean I agree with where you're coming from.
It's like, if he wants to absolutely let him try
it out, get knocked around a little bit, and then
realized it's not for him. I don't think so I played.
I played football all through high school. I don't think
if I was then only child, I don't think I
would have played football in high school. I was like scrawny.
I didn't really like it all that much. The only
reason I really played it was because both my older
brothers were like all state, like superhuman athletes in high school,

(35:36):
and so I felt like I had to like carry
on the lineage did you did you go through a
lake girls spurt? Because I mean, you're six too, aren't you.
So yeah, but I've always been like pretty scrawny, just
kind of like wormy and wiry, especially in high school
like that. And I just my biggest uh and you're
not going to be shocked to hear this at all,
My biggest vice in life is just like I just

(35:58):
don't really ever try super hard, Like I don't. I
just don't care not to put on I don't put
a hundred percent effort into like anything I do. And
I hate that. I hate that I even have to
say that, because it's like that's the most embarrassing trade.
I think that I possess is I just don't care
enough about anything to really try hard. Well, I would
disagree with you in one aspect because I feel like

(36:19):
you try very hard. With Kalen. Oh well, I'm sure
she would probably say something different. No, the thing that
the great thing about Kalin is I don't have to
try hard. It just comes naturally. Um. I think, yeah, thanks. Um.
So when it came to football, football is like you know,
you try shoot, you try a percent effort for ten seconds,
and then you take a thirty second break, and you

(36:40):
try a d ten percent for ten seconds, take a
thirty second break, and over those ten second try hard periods.
I was just like, man, like I don't care, Like
I don't need to block you. You can just kind
of go ahead if you want to. Or like I
was like I was like running around like wide receivers.
I was like I would like runn Aro out and
I'd be like I just like jogging down the side quarterback.
Must I hated you, oh absolutely. And we were the
best friends too in high school, which is a funny

(37:01):
thing too. And I would often be like Dylan, why
don't you ever throw me the ball? Do you like
we're boys, and he goes, Dude, you gotta try. I
was like, yeah, it's probably not gonna have a fair point.
Never mind, don't throw me the ball. Yeah. Well, we're
gonna take a quick break before we get into our emails. Um,
so stay tuned. We'll be right back. Hey, I'm Bethany

(37:26):
Joey Lens, I'm Hillary Burton Morgan, and I'm Sophia Bush.
And we are doing a virtual event in September in
honor of One Tree Hill Day September twenty three, O
th H Day for the O T H Fam And
this podcast family is going to be benefiting Kind campaign
with this event. They worked to end bullying in schools
and we just love them. That's right. The Drama Queens

(37:47):
are so excited to hang out with you guys on
our very special days. So all the information is going
to go up on looped live dot com. There is
more information coming soon. That's l O O p E
d live dot com. The Drama Queens are coming to
you live from the iconic Beverly Hilton Hotel. That's looped
live dot com For tickets. Welcome back to help I

(38:12):
suck at dating, We do have course an email. Ready
to go, Hannah, if you're still out there, do you
want to read this email for us? Of course? Yeah,
I'm going to read an email from a nonymous, oh
anonymous our friend Nick Vile. Thank you very much. This
reads I'm twenty two years old and need advice somehow
to handle my best friend and her boyfriend, who are

(38:34):
both twenty two as well. They have been off again
and on again, and every time they break up, she
comes to me and always ends up saying that she
never loved him and that he means nothing to her.
Regardless of what she keeps telling me, after they break up,
they always get back together. I'm frustrated that she keeps
choosing her relationship with her piece of crap boyfriend over me,
but then once they break up, I'm enough again. Why

(38:55):
would you go back to him after he cheats multiple times?
How do I go about the situation? Please help? This
might be Amelia's best friend undercover like uh falsely giving
ages to make it seem more you know, throw us
off the set totally. She already knows that her and
uh dissick are going to get back together exactly exactly,

(39:18):
on again, off again. You know we're not accusing this
sack of cheating obviously. I mean, I don't know, I
personally don't know, but possible. Um, how do I go
about this situation? Is what Anonymous would like to know. So, Jared,
I feel like you probably have the best advice rations.
I don't know, but I have had friends actually lose
friendships over stuff like this. Because we had a friend
that was dating this guy that we all knew was

(39:39):
a fine guy, but someone who was not ready to
settle down. We used to see him all the time
at bars by himself, and not just like dive bars,
but like bars where guys go to pick up chicks,
you know, and he'd always be dressed nicely and and
look good, and it's like, bro, you're obviously here to
pick up a girl. And then sometimes we catch him
in a lie. We'd see him out and our friend.

(40:02):
We text our friend and we'd be like, hey, your
boys out, and she'd be like, oh, you know, we'd
find out later that he said he was, you know,
at his grandmother's or whatever. So anyway, so they kept
going back and forth, and then one time, you know,
even though we were like, you know, trying to be
supportive but also say that we think he's bad news.
One time, our friend like laid it on the line.

(40:22):
It was like, this guy sucks and you shouldn't be
with him, and they got into a huge fight over
it and they ended up not being friends anymore, which
is so sad. And then fast forward like a couple
of years later, you know, our friend was no longer
with this guy because of course he cheated and of
course he was bad news. But it kind of ruined
a friendship a little bit, a friendship that really was

(40:44):
never rekindled. And so it's hard. This is delicate ground
you're walking on. I don't know what the right thing
is to do. I think the only thing you can
do is to continue trying to toy that line between
letting your friend know that you think he's bad news
and there's red flags while also not you know, like

(41:10):
being as blunt as my friend was. I don't know.
It's tough. Yeah, that's uh, I mean, that's great advice.
I totally agree with everything you're saying. I'm trying to
put myself in the shoes of the boyfriend in this case,
because I've definitely cheated in the past when I was
much younger than I am now because I'm an ancient
human being at this point. But I kind of think

(41:31):
back to like when I was nineteen and I she
did with my girlfriend, and how none of my friends
ever really like nothing they needed to step up, But
none of them ever like stepped up and was like, Dean,
what you did was like messed up. You know, no
one ever like kind of no one help me accountable,
aside from my girlfriend of course, like she dumped me,
blah blah blah blah. I was pissed, not pissed, but
like sad, you know, despondent whatever. But none of my

(41:53):
friends ever were like, hey, that wasn't cool of you
to do, which I in my kindset, I kind of
wish my friends like stepped up and they're like teing,
like get your crap together, you know, stop getting wasted
and going to parties and trying to make out with girls,
Like that's kind of messed up. And I mean if
they I think if that happened, I think that my
relationship life would have turned around a little earlier. And

(42:15):
I it's funny to say, but I don't think this
podcast ever would have sprung up if that were the case.
Not to say that, Like, you know, I stuck at
dating because none of my friends ever stepped up and
said anything to me. But I do think that they're
especially at the age of twenty two, like you are
super impressionable. You have a lot to learn. Nobody likes
you when you're twenty two, right, listen to listen to Swift.

(42:35):
I think that's blank one A two, Right, Nobody likes
you when you're twenty three. Yeah, what's the song that
tell our Swiss things about age? I think it's like fifteen. Anyways,
that's that's beyond the point. My point is twenty two
is a young enough age to where you're allowed to
make mistakes, but you're not. You shouldn't be villainized for
calling your friends out for making those mistakes, especially like

(42:55):
if you have the maturity to call them out for them.
Like I think one of the reasons that of my
friends called me out and nor what I call my
friends out for it was because we all lacked the maturity.
So like if we had maybe like a mature friend
or two would be like, hey, like this isn't right.
We just got word from rally that it was t
Swift sings fifteen, so I was only seven years off.
I was just about to say, Dean, is this going

(43:16):
to sound from there? Oh? I don't know about you,
but I'm feeling in twenty two that was terrible. That's
what it is. Yes, Okay, thank you, thank you, Jared.
I knew I wasn't that far off. Okay, I appreciate that. Two.
And hey, I'm a blink. I'm a big blank win
a too fan, So I am a little bumped. I
missed that reference. But anyways, Um, there's no shame in

(43:38):
calling your friends out for that. I I personally like
wouldn't be mad at you for separating yourself from your
friends that are making those bad decisions, because at the
end of the day, it's like they're probably gonna make
those bad decisions towards your friendship at some point earlier.
So you have every right to say something. And then
if the need to separate yourselves as friends comes about,
I think that's totally fine. Here's a question I have

(43:59):
for you. So Anonymous is emailing us about her friend.
Do you think Anonymous should go to the boyfriend and say, listen,
I love my friend. You can't keep doing this to her. Yeah,
that's a really good question. I think she should go
to their friend first, and I mean, gosh, okay. So
so my story with that same situation is when I

(44:20):
was nineteen, already shared it cheated on my girlfriend. I
regret it obviously deeply to this day. Um. I remember
I was at a house party in college as a
sophomore and my ex girlfriend at the times friend came
up to me and she was like, Dean, like you
you and I can't be friends. I know what you did,
Like this is kind of messed up and in my

(44:41):
in my head, and I said it out loud to her.
I was like, yeah, it's totally understandable, Like I don't
want to put you in an awkward position, like you
have to back your friend more than anything. I don't
think that that conversation had any effect on me because
I already knew I was in the wrong in that case.
But I think that what this anonymous person should do,
let's go to her friend first, and then like maybe
I guess that she sees the boyfriend out happens stantley

(45:01):
say something, But I don't think she needs to go
out her out of her way to say anything like
a glass of water in this dude's face. No, don't
do that. Not even that. Just be like you're you're
a dude, you suck like, get out of our lives.
We don't need you here. I don't what do you think.
I don't think she should do that because then I
think it will alienate the friend. I agree. I think
he's just talked to the friend and be like, listen,

(45:22):
I just you can date him. Of course, it's your choice.
I will always support you and always be your friend,
but as your friend, I also have to tell you
I see these red flags. You know, I've seen relationships
like this before. They always fail. Um, he's addict to you.
You deserve so much better. Um. But then also let
her know that you're her friend and you're going to
support her. Don't give her like an ultimate him, you

(45:44):
know where it's like, hey, it's either him or us,
because then of course she's going to choose him. But
if you show support and you're there for her, and
you try to let her know that I think this
guy is bad news for you. But if you need
to figure this out, then I'll still be there for you.
I think that's the best way to go about it. Yeah,
I agree, but also don't be too slow to pull
yourself away from the friendship, you know, like, yeah, definitely,
don't give the ultimatum. But if things continue to escalate

(46:07):
and stay the same or get worse, like, definitely just
pull out of the friendship. Oh that's so tough one,
and you're losing a friend over this, Like then this
guy won you know, the jerk one. Yeah, you know,
you actually make a really good point. I guess. Yeah,
if they if they're really your friends, stick with them,
be there for him. I don't know, you make a
lot of good points. It's a lot of stuff that

(46:28):
I've really thought of. I think you should be there
for them, but you should also be honest with them.
I think those two things are not mutually exclusive, Like
you can do both. You can say, hey, I don't
like this guy, but if you are in love with him,
then I'll go with the program. But I just hope
that he doesn't, you know, you know, screw you over.
It's hard because a lot of the stuff that I
ever can talk about are like things that I can
draw from experience. I've never had a good friend have

(46:52):
a crappy partner, So it's like I can't I can't
put myself in those shoes. So I think that your
advice is probably better in this case is because you
can empathize with people better and be it sounds like
you had an experience similar to kind of what they're
going what they're going on. So, Anonymous, if you're listening
to this, which we hope you are, thank you for
emailing us, take Jared's advice, but also sprinkle a little

(47:14):
bit of my advice on to it as well, because
I might be an idiot, but sometimes you throw enough
crap at the wall, eventually something's bound to steak. So
Dean's advice is like the grated cheese that the surfer
brings over and he's like, would you like more cheese?
And you're like, of course, just a little sprinkle on
top because I need it right, And then you take
the handful of cheese that was just sprinkled on and
throw it on the floor because you got way too
much cheese, way too much. Dean advice can lead to

(47:34):
a stomach ache. We all know that. Um that's gonna
do it. I think for this week's episode, right, Jared,
you want to answer any more emails or do you
want to talk about anything else before you get added
I think we're good. I think that means we're just
gonna have to come back next week and hopefully suck
a little bit less. That's not our exit, though. I
just wanted to say it back to you, Dean. That
was a little premature. That's what I love. I was
gonna say, I'm shocked. I'm shocked. Um yeah, I do
want to say before we leave, I would like to

(47:55):
apologize for my tardiness. Again. I tried my hardest dinner.
It was a romantic time and that's what all this
that's what this podcast is all about. You know, you're
trying not to suck at dating anymore, and if you
left the dinner early, you would continue sucking. We're working
on not sucking anymore. You did the right thing. Caitlin
has really leaned into this whole help I suck thing.
She goes yesterday, for instance, when I you know, when

(48:17):
she looked up from her phone and it was like
upset that I was getting too close to the car,
she goes help by suck at driving. And today, right
before we had dinner, she goes help by suck at
podcasting and I go, hey, that's my thing, Okay, back
off seal it. But what she doesn't know is maybe
next week we're gonna suck just a little bit less.
Follow help by suck at Dating on I Heart Radio

(48:40):
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2. In The Village

In The Village will take you into the most exclusive areas of the 2024 Paris Olympic Games to explore the daily life of athletes, complete with all the funny, mundane and unexpected things you learn off the field of play. Join Elizabeth Beisel as she sits down with Olympians each day in Paris.

3. iHeartOlympics: The Latest

3. iHeartOlympics: The Latest

Listen to the latest news from the 2024 Olympics.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

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