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Episode description

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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See omnystudio.com/listener for privacy information.

Transcript

Speaker 1

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 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 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 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,

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. 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, 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 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 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

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 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

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 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, 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?

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 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 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. 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 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 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 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, 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, 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 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,

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, 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 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, 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 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, 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 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, 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 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. 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 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 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 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.

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 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 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 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 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 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 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 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 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 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. 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.

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, 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, 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 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, 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 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. 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. The I Heart Radio Music Festival is back. Join us for the official I Heart Radio Music Festival Preach Show

podcast hosted by me Janna Kramer. It's going to be a blast, and we will have all your favorite celebrities and artists joining, such as Christie Mets, Debbie Gibson, Joey McIntyre, Donny Osmond, Degrees, Teddy Mellencamp, and so many more. Get 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 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 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, 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 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 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. 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 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, 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? 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, 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 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, 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 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, 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, 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? 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 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, 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. 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 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 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

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 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 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 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. 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 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 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.

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 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 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 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 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, 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

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 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 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.

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 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 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. 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, 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 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 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 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 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 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 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 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 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 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, 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 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.

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.

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 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 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 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 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 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.

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 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 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

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

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 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 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 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, 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 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 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 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 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 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 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

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 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 or wherever you listen to podcast

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