Off The Vine with Kaitlyn Bristowe - Jared Freid | How a Walking Red Flag Became Boyfriend Material!

Episode Date: June 30, 2026

#958. Somehow the guy who built a career talking about being single... has a girlfriend.Jared Freid joins Kaitlyn to share how he ended up getting back together with the woman he once broke up with, why writing his new book Walking Red Flag forced him to relive every dating mistake he's ever made, and what finally changed for him when it came to commitment.From dating apps and first-date hot takes to the "icks" that are actually valid, Jared shares the dating advice women actually want to hear. He also opens up about taking a year off alcohol, why it unexpectedly changed his life, the surprising reason he decided to try Ozempic, and how he's navigating a healthy relationship after years of talking about dating for a living.If you've ever overanalyzed a text, questioned someone's mixed signals, or wondered if modern dating is just... broken, this episode is for you.If you’re LOVING this podcast, please follow and leave a rating and review below! PLUS, FOLLOW OUR PODCAST INSTAGRAM HERE!Thank you to our Sponsors! Check out these AMAZING deals!Boll & Branch: For a limited time, get 20% off sitewide at BOLLANDBRANCH.com/vine20, code vine20.Zenni Optical: Go to ZENNI.COM/PODCAST and use code PODCAST15 for 15% off your first order.Alloy Health: Get your menopause treatment plan today. Visit my alloy.com and use code VINE for $20 off your first order! #AgeGracefullySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This episode of Off the Vine is brought to you by Boland Branch. For a limited time, get 20% off site wide at B-O-L-L-L-A-N-D branch.com slash Vine 20, code Vine 20. Zeni Optical, go to Z-E-N-N-I dot com slash podcast and use code Podcast and use Code Podcast 15 for 15% off off your first order. Alloy Health, get your menopause treatment plan today. Visit MyAloid.com and use code Vine for $20 off your first order. Hashtag age gracefully. You're listening to Off the Vine.

with Caitlin Bristow. Okay, you guys, I feel like this is just one of those episodes where you're either going to feel very seen or very called out. Today we have back on the podcast, comedian podcaster, honestly, one of the most honest voices in the dating space, Jared Freed. He's back on tour right now, Table 4 One Tour. He's also about to release his debut book, Walking Red Flag, which is exactly what it sounds like.

Just a brutally honest, but actually helpful guide to modern dating. So we talk about red flags, who he's dating, why people are so bad at communicating, how to meet people in real life again, but also why being single might actually be the best thing you can be right now, even though he's not liar. I'm just going to ask him everything you guys want to know,

so let's get into it with Jared Fried. Like, I have this book coming out, and all I can think about is like, I kind of had this moment just now before I came here. I'm pushing it. I want people to read it. I think it's a laugh every page. Yeah, I love that.

So, like, would someone like to laugh every page of a book? I would. I made the attempt to make it. you laugh every page of a book. So that's good. Yes. I'm proud of you. Thank you.

Writing a book was not something I saw for myself. I've never even read a book. I've never even read a book. You've written a book? No, I haven't. You didn't do a book? No. I felt like you would have done a book.

I know I seem like I'm in that world where that would be the natural next progression for me to do as a book, but I have not. Don't do it. It's a horrific process. I've heard it's tough. It's tough. And you know what was tough about it is. it's a dating book. It's a dating advice book.

Yeah. I'm giving perspective of my, my opinions on dating and the premise is that my opinions on dating on every step of the process from getting dumped to being dumped again. Yeah. That's all the book is about. Because that's all I know. Getting dumped to being dumped again. I only know. Have you always been a dumpy? I'm a dumper. Oh, you're a dumper. I end things before the next step. Is that like I quit before I get fired? Yeah. Well, no. I'm sorry to interrupt. I got ahead of you. I'm sorry to the commenters. I got ahead of Caitlin. No, it's a, it's a I quit before I have to find out what happens next. And I think a lot of men do this where they end things before the next step. And this is what the book's about. I, I, I use the word I. Not, I tried to say I. Yes.

But I am like, I'm within 10% of any guy you've ever dated. Okay. So if you read this book, you're going to get answers from me that will answer questions to get you inside the mind of any red flag you've ever dated. If you want closure from a relation from five years ago, why did he end it five minutes before we were supposed to be? You got an answer for that. I got an answer for that because I have an answer for myself and my own feelings. So that was like the whole point of the book is like let's let me talk about dating in a vulnerable, honest way. And not in an accusatory way, not in a mean way. and that's something I've done forever.

Like, when we talk about dating on you up, it's very rational. It's very, we try to have fun with the subject. We try to make fun of it and make, and make you laugh. But at the same time, there's no hot take. Like, I would never tell someone coffee dates are stupid. Like, coffee dates are good for some, better for others, worse for some, worse for others.

Coffee dates can feel like a step down. I can understand why that would feel like that. Do people think this? Yeah, I think if... I love a coffee date. I love a coffee date. I think a wine bar with a coffee option is the ultimate first date spot. Yeah.

There's a place down in the West Village that I love, I think is the best date spot. I bet you I have it written down. Every woman has a list of places. I mean, I can't believe I'm forgetting the name because I just haven't been there in a minute. Well, I'm going to look up my list. Look up your list. I will tell you mine if you tell me yours. St. Jardine.

Oh. St. Jardine to me is a perfect. date spot and there's even a place down the street that's as good and not as busy called let me do St. Jardine this is great radio St. Jardine and then I would also say

down the street it's next to Fadora. Is it called Bouvette? Not Bavette. I like Bavette. Bavette is also a great spot for a date. Okay. What about Dantes? Dantes is is a good spot, tough to sit. They never have seating and they don't have a bar scene. There's no real walk-in and they're a coffee place.

I know Dante opened a coffee place. That might be better. Okay. But the one on Hudson and the West Village is not a place. A tough place for a date because it's just tough to like keep it casual. But I'm saying like, yeah, any other place? Well, have you ever had the elk for coffee? I love the elk.

I love the people with the elk. Do you know that my girlfriend from Vancouver opened it? Really? Yes. I've met her. I used to hang out the elk all the time. Really? When I first moved to the West Village.

Claire, sweet little Asian. Yeah. Yeah. Her dog's name is tofu, but RIPB. I've met Claire. She's very nice. I love what the elk does. The elk is like a picture perfect.

That's what Sarah Jessica Parker promised young women would get when they moved to New York City. That is the sex in the city dream. And Christina works there is wonderful. I've been going in there since I moved to the West Village. That's a great place because it's like you can pick up a coffee and then take a walk. There's nothing wrong with that date. And there's so much talk about,

there's so much negativity in dating and like what to do and that's wrong and that's right. It's like, I can plan a $7 date that both people really enjoy. Yeah. Anyone can. Do you find that dating now Florida's different from New York?

The problem with Florida, when I moved down there, I was single. I'm now in a relationship. You are? I am. Thank you. Look at you. It's right. Sorry, ladies. I'm off the market. It's over. For everybody.

Sad day for the women of America. It really is. Sorry. I know you guys were a little moist when I was talking about date spots. As soon as you said you could figure out a $7 date, I was really slipping off my chair. I know. That's what does it to the ladies. Oh, a cheap date?

Yeah, I'm very happy. But when I moved to Florida, the problem with Florida dating, everyone had a story. Everyone had a horrific story that you didn't know, or not horrific, but like the difference between New York and Florida, in New York, people were trying to do something. And in Florida, something had happened. So it's like, why'd you move here? Especially 41, I was dating women probably 27 to 42 around that age. And they would, you know, well, I moved here because here's what happened. and New York, and especially this is when people talk about like the disposability.

Well, if you're here in New York to meet, if your only reason for being in New York is to meet someone, you're spending a lot of money to meet someone. Yeah. So most people move to New York because they're looking for the career. They're trying to find what makes them sprint. Yeah. And if you're here just looking for a partner, that's why it can be exhausting. for someone living in New York

because you can find a partner in any other place without the cost and without being someone's second choice. Because I was in New York dating. I'm here to be a comedian. I'm here to, you know, I'm here to be, you know, grow my, my,

comedy and get better at stand-up and go on the road from here. And then once I was like getting that done, like, then... Yeah, you can go to Florida and then still continue to do it on the road. Right. That's kind of the. thinking. That's why I moved. Your parents live in Florida?

They live in Boca. Do you love being closer to them? Because I know you're close. I do love. I have fun. They are a sitcom episode. Like it is, they live in a country club. Yeah. They, it's sushi night every Friday. Ugh. I go there and get to hear about how

thinner fat I've gotten. And then I leave. And your girlfriend's met them? So she, yeah, so she lives in Philly and. She lives in Philly. Yeah. Wow. So we, so we, dated. Go birds. We dated two and a half years ago, almost three years ago, and I couldn't get to the next step and I ended it. And then we didn't speak. And she forgave you. You know what? When I ended it, she understood she was like very, I wrote about her in the book. Oh. That's the weirdest part is that. Before you even got back together with her, you wrote about her in the book. Yeah. So over the course of when we were broken up, I was writing this book. She knew about the book that was like, it was

being proposed at the time. And then when we, and then I was writing about, you know, one of the parts of the book at the end is like about, you know, I've been dumped and like, do I call them back or do I let it be?

And I talked about different women in my life, some that called me back and some that let me be. And she was the one that let me be. And I remember her saying like, listen, you know, you have my number. and then we kind of walked away from each other

I remember it was the West Village I can remember the street corner I remember and then I remember ending it and thinking like that was either what I needed to do or it's like a horrible mistake and then over the course of the next couple years I would see her looking at my Instagram story

and take more away from that than that meant you know or was it exactly what you thought it was right I don't know I just felt I was like, you know, I was like in Australia thinking about her. Like I was in the, and like having moments of like, and I didn't want to reach out because like, again, because I'm in this space. Yeah. Of dating and relationships.

I know. And I'm also 40, 41 at the 40 at the time. Do I want to mess with this person? My greatest fear with it was like go back and then feel the same way indifferent. Right. Or feel not sure. But that's not happening. So then when she, so I get.

So I'd always be like, well, if I get to this point, I'll text her. If I'm still thinking about it, text her. And I got to, I was going to have a show in Philadelphia and I, there was the week before and I got a text from her. Hey, do you want to get coffee? I know this is out of the blue. I keep getting your sponsored ads. Your promoted post.

The world will not let you out of my sight. No, right. Can you imagine that's like hell. Oh, I immediately didn't. You know this. I mean, you know this again. Right. there was a button for that.

See, she didn't press that button. No. So then we get, so I had my show and then I was like, let's meet after my, like the next morning. Yeah. And we got coffee and I remember just being like, she just seemed so happy. Like I, and I, she had like a brightness. And I was like, I was like, I, you know, there's a fear of like, I don't want to mess

that up. Yeah. I don't want to be the, this person's problem. Yeah. But I was also like, you know, you've thought about this. Yeah. You know, I wasn't bullshitting. So that's kind of how we...

Well, and you have a different lightness about you. What's going on? Well, I don't know. Girlfriend. Are you still not drinking? I haven't drank in like a year. I'm so proud of you. That's okay.

Thank you. It's okay. I took a month off and then... It turned into a year. It turned into it. It wasn't because I was like, yeah, and I'm happy with the way I did it. Yeah. And it's been, you know, I always say I'll drink again.

Yeah. Just because I like drinking. Me do. We love a martini. I love a martini. And I like, sometimes I'll see it. There's a bar near me in Florida where it's like a dive. And I'm like, I can feel like my body move towards it.

Yeah. That might be called alcoholism, but that might also be called. I kind of have this. I keep saying, I got to drink. drinking Del Rey. I got to see what it's like. And I just haven't done it. Well, and part of it was like, you know, when I was, I was with my dad, we're playing golf and this was a year ago. And he's like, what would make you happier? And I'm like, okay, what, what sitcom Danny Tanner thing are you trying to do right? Was he wearing a sweater?

He's in a sweater, ugly sweater. The music started playing golf. He's like, what would make Jared happier. And I was like, I think if I took a month off just to see, really to see I could do it. I do this, yeah. Right. You got to make sure. You got to check in with yourself. And then I went, I was like, well, but I have Rochester coming up. I, yeah. And I'm like, I got a drink in Rochester. It's a horrible place. Yeah. I love Rochester. I love the shows there. And then I'm like, and I got Nashville coming up. I got a drink in Nashville. It's the most fun place in the world. And then I'm like, well, if I'm saying that I got a drink when it's not fun and when it's fun, maybe I need a month. Right.

And I had this wedding that was like May 9th. And I was like, okay, once I get to the wedding and a little bit, you know, now thinking back, I'm like, I keep thinking of this other girl that I ended things with. And maybe it's the alcohol. Maybe it's that. Maybe it's all mixed together. Maybe the alcohol once I remove that. And then I got to the wedding and I was like, you know what? I can keep it going.

Yeah. And then I got to like the, or the, it was like the Friday night, everyone gets their thing. I was like, I'll keep it going to the wedding. And then I, then the wedding, I was like, I don't really need it. Yeah. I feel like that happens. I've gotten to that point too where I'm like, I'm going to take a month off. And I was like, I'm just going to keep going now.

I haven't taken a month off in quite a minute. But I have completely changed my relationship with alcohol. Yeah. And it's very hard to do in New York City. Oh, my God. Well, that's not living here helps. Totally. The one thing that made me stick with it

And this is just the sleep And that's like a No The sleep is really I like waking This is like the most 41 year old speech ever I like my mornings I like waking up

I like feeling you know the Do you wear an or ring? No Just a Rolex Just no not even a Rolex This watch It's nice I get more comments on this watch

It's beautiful Plug City I know they're not a sponsor I don't they I'd love a free watch If they'll give me one. Didn't we talk about these watches last time you're on my podcast? Maybe I did.

Mr. Eatwell? I don't know. I just remember. No, swatch. Swatch. I'm a big swatch guy because they were 100 bucks a piece. And you could get different ones and change you off. And then this Mr. Eatwell thing came up on my, like on my sponsor.

And it kept hitting me. And they're like pretty well. It's like a $350 watch. You would think it's like a thousand bucks. It looks really nice. It looks expensive. It is not. Which is even better.

And it's got some, I'm a car. colorful guy, like a little color. A little pop, right? But I hear what you say on the sleep thing because my aura ring like keeps me dialed. Because if I have a bad sleep, I'm like, well, I'm not doing what I did last night. But here's my problem is alcohol doesn't really affect me the next morning. It's bizarre. You don't get hung over?

That's like a magic power that can be like a curse. It is a curse because then when I go out in New York, which is apparently all the time now, I'm like, I don't get hung over. I don't like getting drunk I like having to drink Yeah I like feeling a wee No it's the full body That's why martini is so good Martini when you have a martini

And you get done with it Like I honestly if I could If I could if I drank again Give me one martini And then just keep filling Martini glasses with ice water and olives Totally And just keep them coming

Totally I can never have one yeah I'll pay I'll give you whatever the Give me half price Wow I would go half price. I think in this era of like, because bars are struggling right now. Right. That's my biggest thing with, I like being in a bar.

And I don't want to screw over the bartenders. I know a lot of people who do bartender and service industry people. And I'm like, just charge me half. Yeah. And fill it up with water. Fill it up with water. Like a non-alc beer, I really do enjoy. I've been enjoying that.

They taste so refreshing. They're good. Yeah, and then you don't feel like shit after. And I get it. And I get out of it. What do you mean? Like the hand to mouth, the... Oh, and like just the feeling of like the sparkly...

Yeah. Yeah, yeah, yeah. I get the ooze. Yeah, yeah. Oos. And yeah. And then I... So then I was not drinking and my dad goes...

He goes, I thought I'd kill two birds with one stone. It's nice that you stopped drinking, but I thought you'd lose some weight. He did not. I swear to God. When he said, I thought I thought... I killed two birds. That is not a Danny Tanner thing to say. No, no, he's now he's, you know, Danny Tanner's evil cousin.

That's so funny. It's crazy. So that's what I'm talking about in my stand-up is my dad offering me his Ozempic. Does he offer you his Ozemp? That's how it all started. We were at dinner and he goes, take my week. And did you? No.

Oh, okay. And now I'm on it. Oh, you are? I'm on it now. Vitamin O. Love it. I would have been on it a year before if my dad didn't offer it to me. Oh.

I was so insulted. Oh. You're like, I'll show him. Well, it's like not even I'll show him. It's like, I don't think that I'm like embarrassing myself leaving the house. Right. When you're offered it. Like, like, what do you, what do you think of?

Like, did you think it was crazy I would even leave this way? Like, do you know what I mean? Take mine for a week, son. Please. Please. Look at you. You need it. Right?

I don't want to be told I need it. And then I got on it. I am just such a fan. You know why I got on it? Tell me. Two people convince me. Your dad? No.

My dad, him. Ben Soffer, boy with no job. He talked about it in a way that I'd never heard someone talk about it. He was talking about it in a very, like, lifestyle way. Okay. Not an event. Everyone talks about it in a vanity way. Yeah.

And then my dad's friend Al Horowitz is an older man. Yeah. Older. Like, and he's like, it's the best drug I've ever taken. Really? And he's not like getting ready for spring break. This is like Al Horowitz, old man. But he used to run marathons and he's been a healthy guy his whole life.

I, you know, my dad's been friends with him a long time. We all played golf together. And he's like, it's the best drug I've. ever taken. And I'm like, why he's just, and I just couldn't believe that this guy were vanity. It's not like he's out trying to like, fuck. Well, Hollywood has really made it seem like it's like, ooh, skinny's back. Let's all get skinny and frail.

Seemingly. What I think is there's a lot of information on it now, a lot of research. And even my doctor was like, well, you could do it for inflammation because you get really bad Periods, sorry to tell you that. My ears! Can you imagine if I heard periods? Periods! I'd be like dump him.

A new girl, dump him. I am a person that when I get beef jerky. Okay. I get mad that the salt packet that comes in the beef jerky to keep it dry isn't more beef jerky. You're like, there's room for more and you add the salt packet. No, I'd be sitting there chewing on the salt pack I'd be like, can you please be? Like I just like had this like I couldn't.

You didn't have like a full cue like when you were full. No, I have none of that. And I would live in fear of the moment. I would break my eating. Like I went on Jeff Lewis Live. Oh. Which was fun. I liked that guy.

He was really nice to me. He did like a pre interview or pre. Pre-radio hang. Okay. He tells you to get there at 8.30, they start at 9. Okay. So I get there at 8.30 and there's this bake goods on the table. Oh, no.

If I had not any other time, I'd be like, don't touch it. It's 9 a.m. 8.30 a.m. You'll be done for the day. You'll see me naked in an alley with, you know, with dominoes all over my body. Like, if I start now, it will not end the whole day. And then this woman turns around, she goes, do you want to try my bread pudding with Biscoff cookies and Carmel? and I'm like, and it's Carney Wilson. Oh.

And I'm like, Carney Wilson, this is crazy. And I'm like, it was like the most LA moment. And Carney Wilson's like, I love to feed people. I saw your stuff. You seem so funny.

She was so sweet. Yeah. So nice. Do you want to try my Biskopf cookie, baked, you know, bread pudding? And I'm like, I'm like, I love Delta. I love Biscoff cookies. I also love Delta and Biscop cookies.

Right. And I go, and. I was like, yeah, I would love to try it. And I had one piece and I ate it. And then you didn't go back for more. And then I was done. And it wasn't this like monumental thing. And I had the thing that I would have, I had the happy moment.

I didn't act like a crazy person. Yeah. You know, I got to have, I got to like talk with Carney Wilson in a way that didn't have me going, I can't. Any other time it would have been like, Carney, I'm sorry, I can't. It'll ruin me for the rest of the day. And she'll be like, you don't want my. It would have turned. into like, but then there's a piece of me that's like, do I lose my funny?

You know, that's like, these are the things that would create a story in my life. Did you worry about that with alcohol? Alcohol, not as much. Because I never was a fun, I'm not a fun drunk. I was never a mean drunk, but I was a drunk till I get quiet and order DoorDash and then go home and have two different, the DoorDash guy and the seamless guy meet in the hallway and realize that they were going to the same apartment. That's the type of drunk I am.

That's like me if I smoke weed. Okay. Yeah. Right. So I never thought it was like losing me funny. I think with alcohol you, it is when you take away alcohol, you lose. It's tough to be social. Yeah.

It's tough to like have a reason to go out. But that's why I probably wasn't losing weight because I'd just order a bunch of food. And I'd be at a bar with like, like, who's that guy that ordered. seven orders of appetizers at the end. It's like, yeah, those used to be martinis. Well, you do when you walked in, I really will say, and I'm not saying it so you can not ever go back to drinking or that you need to stay skinny or whatever. You just have like a lighter energy.

I feel good. I feel happy. I mean, like, this is like a really good part of my life that I don't want to lose. Yeah. You know, like. Okay, something that I always realize is that we don't notice how worn out our bedding is, because it happens just so gradually, I guess. Maybe your fitted sheet won't stay on the corners anymore.

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I had a stand-up special that I was trying to sell that was really important to me. And then it got sold. So it's going to be on Netflix in the fall. Great. That's great. It's called The Family Plan. It's a one-hour story about going to the beach with my parents. You saw that show.

Okay. I was going to say, is it the same? It's hilarious. You saw it. Thank you. Yes. Okay. That's the one.

It's so good. So it was depressing me that I couldn't find a place for it. And I'm like, what am I doing all this for? Like I do this. I go on podcasts. I go and I say things about my life. I make the videos so that I can do stand up. And now I have this piece that I'm really proud of and no one wants it.

So that was kind of weighing me down. And I was going on dates with people that were very nice and I wasn't feeling the, you know, the feeling that I knew that I could feel. I do believe in romanticism and those things and being carried away. and then the book I had to write about it. You know, the book was the hard. So the food book about red flags.

It's about red flags. So I hired a ghostwriter. I wrote the first, I wrote the first, they go, you do the outline. So the first thing you do is this huge outline. And then they're like, okay, write page one. And I remember I was like in Denver and I'm like, okay, I'm at my computer writing it.

I'm hating it. I'm an idiot. What's this? This is so stupid. It's not funny. Stand-ups, we want an instant. feedback. Totally.

And this is the least instant feedback. This is two years ago. And I sent in the first page. I go, okay, I'm done. That was horrible. 20 minutes later, they're like, we need a ghostwriter. Side note, we will need a ghostwriter. Right.

So now I didn't talk to the editor for a month. I was so angry. I was like, in the beginning, I was like, well, where's the ghost writer? Right. You know, I'm like, we need one. I've never read a book. And they're like, oh, you don't need one. You can do it.

And then so then I didn't talk. talk to them because I was like, these people, I'm taking a minute. Yeah. And they're like, okay, a month later, like, Jared, hey, hey, hey, yeah, you there? We need to hire a ghostwriter. And I was like, I want them to be a woman comedian, female comedian, because I've always put my dating stuff through women. Yeah.

Because I do want the feedback. I do want to have the debate. I do want to tell you how I feel. You've got a female followers, too. It's not by, that wasn't my, I didn't get to comedy for that. But it just kind of worked out that way. It's great. Yeah, bar stool.

They're like, who the hell is this loser? You know? And why is he not? Timothy Shalley jumping up and down like a 12-year-old girl over Backstreet Boys. Why is he dressing like he's me in high school trying to look like the cool kids? Timothy Shalemay's outfits every week is a new 90s outfit I would have been embarrassed about. That's so funny. But I feel like the women are also.

the women, the girls, the Gen Z girls are also dressing like I dressed in the 90s. That's true. It's all coming back full circle. Yeah, I find myself relating to that group less and less every day. I know. It's hard for me. Because even his body type, I'm like, he's the sexual icon. I can't look at him like that because he looks like a little boy to me.

He does look young to me. He looks so young, especially when he's like jumping up and down. I will get there because we're going to talk about the ick And I have a new thing Please I love it We'll get there But anyways yes So you got the ghostwriter

So get the ghost writer Taylor Taylor K Phillips who writes for John Oliver Like again Like couldn't be the more Like hilarious comic who is like It's like right brain left brain Yes

Like she's like getting it done On their shit Great jokes so funny And we I told her I was like Email me questions every night and then in the morning I'll get back to you. Yeah.

So every morning I'd be on my phone writing back to Taylor. Yeah. Stories from dating. And I didn't remember the stories until she was like, do you ever bring, did you ever bring, get brought home or get brought to a wedding? Did you ever, when you downloaded the apps, do you ever have a time that someone was like annoyed you or like all these little kind of openers prompts that would get me to like, oh there was this one time and then I would call friends I'd be like remember that story I told you

and so now I'm having to review my life yeah and I'm like in a coffee shop crying while writing these like reviews and like again like to bring it back to my girl my now girlfriend like you know I have a story in there about bringing her to Chicago and how much and I I just really didn't do the trip right like I I felt so much regret from it and you know, if you've dated someone, you want to go back to them, just have them write a book. Because they'll get to review their life. But it was really hard. So I did to go back to like why I was like, so I'm like doing this book where I'm having to review every dating thing I've ever done and whether I want to be in this place of life.

You know, I was when I was turned 40, I was on a flight to New Zealand alone to go do shows. But like, this is the life you build, Jared. This is it. Right. You know? Did you ever get like, I think I could be single forever? This is fine. Yeah.

Yeah. I don't think there's anything wrong with single. No, no. I do think you have to start filling your life up with things. You have to make real, you have to really work at like filling your life with things that you want. Yeah. You know, you have to do a certain amount of work. Yes.

To be single. Because you don't have anyone. to answer to. Right. And that's... Then when you get into a relationship, are you having trouble with that? Because having to answer to somebody after being single, how long were you single? I mean, dating, of course, but like... I was single. I was in, I was, I was, I live with someone in 2020 till 2021. So 2021 is really when I was like... So then you get in like your habits and your routines and you have the structure in your life that makes you feel good. How hard is it to mesh with somebody else? Or is it fine because you guys are doing long day? We're doing long distance right now.

going to move to Florida. So like that's already happening. Oh, yeah, yeah, yeah. Yeah, this is happening. Has she read the book? Yeah, that was the first thing I said. I was like, you got to read the book because you're in it. Yeah.

And she loves it. Oh, that's amazing. She like, you know, she, no, I feel very lucky. And it's, you know, the book, you know, her coming into my life. You know, it is hard because you have to, you know, what happened with that meeting? You know, what happened with Caitlin Bristow? Yeah. I could leave here, go, in my mind, I'd go, that went well, we had some laughs.

I got personal. We promoted the book. Good. Done. And then I can go on my way. Now, how to go with Caitlin? Now I have to like. Elaborate?

Present this to her. And now I have to hear, well, what about you didn't bring up? and now you go, I guess I didn't bring, I could, I just said it to her better. You know, sometimes I'll say things are better afterwards. So it's like, it is, there's growth in that. There's, there's, there's accountability in that. There's. Yes.

But it's also, also owning that you're not bad, you're not as great as you think you are in your head. You know, I think like that's the problem with like men as they get older and single are people. like you go I'm the fucking best and I did that great and you have a like I think that too like I'm the most chill

awesome girlfriend there it could possibly be on this planet unless you fuck up something with my dogs you feed them wrong you look at them wrong

you do it but other than that I'm like go golf all day I'll see you tomorrow go out with the guy I don't care I don't feel like I but then you're in it

and your guy says something like, yeah, the dog, I don't know what you're doing with that dog. Like, why'd you do that with the dog? And then you have to answer to it. And you're like, I'm enraged by this person. Enraged. Yes. Relationships are hard, though.

It's hard. It's hard. I think that's been the hardest thing because her and I, like, also I'm 41. Yeah. And I've had a dating podcast. I've talked about dating every day. Right. For 20 something, almost 20 years.

So it's like, you're awesome. It's not that I think I'm awesome. just know where I know how I want to do it in this phase of life. Totally. You know, at 41. That's a joke, by the way. I know you. What's that?

I wasn't like, so you think you're awesome. I wasn't really serious. No, I just feel like I'm more like a guy who's off his first divorce than I am newly in a relationship. That's the dream. That's kind of how I feel. Yeah. Because like even like she's moving in, I'm like, money. What are we going to do?

Yeah. I said that, you know. Yeah, you just get out there. What are we going to do? Yeah. How are we going to do the rent? how much do you pay for your rent? Here's how much I'm paying here.

I just bought this place. How do you feel? I want you to feel like it's your place. Like, I want you to feel like you own this place with me. Yeah. And those are things at 20 I couldn't do. I wouldn't have the mechanics. And that's why when someone's talking, you know,

you got together with your high school boyfriend and now you guys are married forever, it's just different than what I'm in. Yeah. And the way a guy in his 20s fucks up, I have a lot of empathy for, and I'm here to speak for that guy because I've been that guy. I don't think I'm above that guy. Like I think right now there's a lot of hot take artists

where, and especially on the internet, you can crush men. Yes. You can go on there and be like, these men don't know how to talk to women these days. And it's like, we'll fuck off. Go talk to a woman. Go talk to a woman.

You want to see how good you do. Guy who's married already 10 years. It is crazy how everybody's experts online, though, whatever they decide to talk about. And just mean. Like no empathy because you have to come out with this like hot take opinion. Men don't know how to talk to women these days. That's really easy to say on the internet.

Where men are just hammered on the internet every day. And it's like you have taken no chances. Yeah. And they think, oh, this is what women want to hear. Of course. It is what a lot of women want to hear. It's a lot of single women want to hear. Yeah, because guys are coming up to them in bars.

Okay. Well, let's talk about that. Okay. Do you think that's where I remember you said someone. I haven't written down. Oh, you talk about meeting people in bars is actually still a thing and a good thing. It's better than an app. You've done better.

You are literally a human being who left the house. I'm not saying that people aren't talking to people less than bars. I'm just saying it's hard to do. I agree. And it's hard when you have a crutch. Such a crutch. And chat, GPT, copy, paste. What's a funny answer to come back with this?

What's something we can? I probably said this to you last time, but we're living in a reality created by low confidence nerds. So the dating apps were created by men who don't want to talk to women nerds.

And I say nerds in the I'm a guy who doesn't want to talk to women and can't talk to women. It wasn't made for the guy who goes to a bar with his friends and can talk to women. Yes. And has the ability. But that guy still uses the apps. So it's a crutch.

So you think the good guy are going to the bar to meet women because they have the ability to strike up conversation to actually like meet someone face to face. I don't know about that. I would say that I would say if I was to like give an advice as to like if you're like where are all the men, men are doing activities. Yeah. Men love activities.

Where are they? You know, it's top golf. It's axe throwing. It's bowling. It's shoulder to shoulder activities. If you are like a woman with your two friends who wants to go find men, go to a place. I hate, no, not Home Depot. That's like what a mom would say.

Home Depot. That's where they're hanging out. They're looking at two-by-fours. No, I just think men love activities. The Knicks are in the finals right now. Go to a Knicks game. Go to a bar where they're watching the Knicks game. Yeah, right.

Go on the Knicks. Hey, who you got? Commercial break. break. Oh my God. How long have you been a Knicks fan? Do you love them or are you just here because it's a party? Those are all great questions. Love your shoes. I always say love your shoes.

Oh, yeah? Your shoes are awesome. Thanks. They are awesome. I like them. They're pretty sweet. Your shoes are awesome. It's such a great opener. It's positive. It's friendly. It's not sexual. It's not about a shirt that's over, you know, it's not boobs and ass. Yeah, yeah, yeah. It's shoes.

See, I'm so inappropriate. I don't know how to flirt anymore. doesn't matter, but I would literally probably say to a guy like, can I see your ass? I need to see if I can rest a drink on it because if it's not big enough, I'm out and I need to know immediately. I mean, and most men will go, let me bend over so you can put this on my ass. But if a man did that to me, are you? Right. You kidding me.

Get him out. You turn out. You get out of him. You know, so this whole idea, like where do you meet a guy? I would also say, and this is my. This is a big part of the book. Okay. And this is my summer dating challenge.

Okay. My last summer dating challenge got stolen by that kooky old woman. Which one? You know who she is? She's on social media. She's like, go to the sit alone September. No. That was my thing.

Stop. That her intern listening to you up and stole it and then admitted to it. Oh, really? She was like, oh, I used to listen back in the day. Oh. Yeah, sure. Sure. Crazy old kook.

So that, my. new one and a big part of the book is like you got to hang out with your friends who are married. You go hang out with your friends that are married and hang out with their spouses. Yeah. Oh yeah. Hang out with both of them. And it's a big thing in the book and I know women avoid this because and it's something to get over. What?

The idea of bringing anyone into your dating life because then you have to answer to it. Just like we were talking about, how to go with Rick. Right. A lot of women don't want to answer that because it's now becomes this like, this test they didn't pass. Right. And I don't feel that as much. I don't think societally I'm put through that type of questionnaire on a daily basis. So I do understand that like letting your family fix you up and having a friend get involved in any way can feel like, but it can feel horrific and like,

a total thing you want to avoid. But I would say that people are tired of the dating apps because they're tired of just wasting their time. It's such a waste of time. It's such a waste. Do you want dates or do you want quality dates? Yeah. The quality dates are going to come with someone who has someone to answer to, especially men.

Yeah. You want a date on Main Street, not in the alley. Dating apps are for alley dates because no one knows about them. Do you think it's the worst place to meet somebody is on an app? No, I don't think anything is good or bad. Oh. Just is. Okay.

You know, it's a tool. It's a hammer. Is a hammer bad? Got it. You know? Hammer's bad if someone swings it like a crazy person. That's fair. So there's a lot of people on dating apps swinging them like a crazy person.

So there's a lot of people acting badly on dating apps. How do we protect ourselves? Right. You got to, I think, you know, the podcast, the book has always been about being a better buyer. Yeah. So why do I say go to your friends? Well, so my summer challenge is it's, it's. the summer of strut.

Okay. Go on a strut with 12 different friends this summer. Just like a hot girl strut? With a friend. Okay. Plan it with a friend and invite the spouse. Okay. So right on a list, 12 friends.

Okay. If they're single, just go with that person. Maybe you bring another single person along. If they're married, make sure the husband comes. Okay. The husband's not going to set you up. I'm just letting you know. No husband wants to set you up.

No husband has a friend to set you up with. That's why when people are like, all my friends are married. All my friends have kids. They're right in the excuse, but they're negative and they're not to be set up. Yeah. They're actually doing it wrong. Yeah.

If you say the words, my friends are all married, my friends all have kids. That's why I'm single. You are the problem. Okay. Just you have to look in the mirror. Yeah. If your friends are all married, that has just doubled the amount of people you might be able to meet. glass half full, glass half empty.

Now you go, well, my friend's husbands never have a single friend. You don't know that, first of all. Second of all, that's not what you're going to get from your friend's husband. You're not cool enough to set up by your friend's husband. Okay? You've got to start marketing yourself to be a better setup. No one wants to set up the person and goes, my friend's husband doesn't set me up. Yeah, I don't want to work for you.

I got my own life. And that's a big responsibility. Totally. So here's what you want out of your friend's husband. At a minimum, this is the best you'll get from friend's husband. Yeah, she's cool. Yeah, I know. Totally. Do you know what I mean? Every guy who's ever met their friend's friend who's single, all you want out of him, oh, she's cool. Because now your friend is going to go, what about your friend Rick? And he's going to go, oh, Rick's, yeah, I think he's single. And then your friend's going to, and then Rick is going to go, what's she like? And he's going, yeah, she's cool. Yeah. Yes. And that is like the biggest recommendation a guy could ever get. Yeah. Yeah, she's chill.

She's chill. Yeah, she's fun. She's actually fun. And cute. That's beyond. Okay. The cute part is way too much. Women kind of lean on the cute part way too much in my opinion.

To me, it's like everyone has different types. I can't. I've been given a picture of a person's friend many times. I've been like, it's not my type. I'm not going to be like. Yeah. It's not going to be my game. Yeah, that's true.

So pretty, they won't go on the date if you're not attracted to them. Yeah, right. But the recommendation, yeah, she's cool. Yeah. Is like huge. That is huge. If somebody, if one of my, like, a friend's husband said, oh, yeah, she's chill. Right.

Game over. Like, right, you would love it. Love it. It's like Coca-Cola. Like, Coca-Cola has ads on TV. Yeah. We all know Coca-Cola. Yeah.

Yeah. Why do they have ads? Because they want your, they want Coca-Cola be the first thing you think of when you're thirsty. Uh-huh. So we want your single friend to be the first thing you think of when you think of single woman that's cool. That's true. I saw something on, you know, those trends where they're like, I'm bored, tell me what you would call your ex as like a brand. Somebody was like, Pepsi, because Coke was a problem.

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Head to M-Y-A-L-L-O-Y.com and use code Vine to get $20 off your first order. What do you think is something women think is a red flag that you actually don't think is? From a man? Yes. What I don't think is, being single, not have her having. having been in a relationship. Yeah. I don't think that's a, I really, I think that gets played up too much.

I think people are embarrassed of it too much. I agree. Never having been married, never having. And I'm saying that as someone, you know, I'm trying to defend myself. I think that's like attractive to me. If somebody, first of all, I'm, I like both. If you're a divorcee, I think that's so hot. Right.

And if you have just waited and you haven't found the right person and you're 40 and you're like, oh, I'm ready. Everything has, all that matters is the story. Yeah. If you, you know, if you can, hey, I've never been married, you know, so, hey, I'm 40 and I live with my parents, people will go, oh, well, stay away. But if I was like, yeah, I'm 40, I was dating someone for a long time. And then, you know, my parents had this extra room in the house and I could save a bunch of money

because I'm really looking to, you know, buy a home soon. Yeah. My career is doing really well. It's actually I've just gotten a promotion. I'm a lawyer. And I just love my parents. And this is kind of this weird way to live where I can live in the next room. And we don't bother each other.

And it's really more of a friendship. Now, look at how I'm talking about it right now. Yeah. You would make that exception to go on one day with them to see what it's like. Absolutely. Of course, you don't want them living. If they're like, well, I'm going to live here forever and whoever I date is going to move in with me.

Because I don't have a job. Right. Totally. I agree. Okay, what's something women excuse that you're like, no, this is a problem? They excuse, I think women tend to excuse, I'm trying to think of what I've gotten away with. That is an actual problem. I think they tend to excuse being told that it's just social media. It's just social media.

I think that's like a really... I think when someone says it's just social media, you live your life on social media. It doesn't matter. Yeah. There's real life versus social media. That's them making something that is a real thing into a...

What, like if a guy likes an Instagram models... Liking Instagram, you're making too much of social media. I think a lot of times women will hold that against themselves because what they're doing is they're trying to say that they're morally better than you. they're saying anything with social media has lacks morality. Oh, yeah. And is small and simple and stupid.

But that's really not true. Everything matters, everything doesn't. We live in a world where social media is a part of the conversation. We live in a world where it's a part of your dating life. Now, if you're dating someone who never had social media and then you're saying, I want to take a picture with you and they're like, I don't like to be on social media. That's why I don't have an account. There's a reason for that.

But if they say, I don't, social media is stupid. You care what all your friends think. I think you're being demeaning. Yeah, I agree. To something that people do care about. Yeah. And I don't think that's like something small. I think that type of jiu-jitsu is a bad person at date.

Like, if their first move is to take something that matters to you and turn it into morally bankrupt, that's a bad person a date. Yeah, that's fair. That's fair. Okay. I got to talk about the ick. Yes. I give all my icks in the book. There's a whole thing of icks.

And just joke, joke, joke, joke. It's all jokes. I got one the other day. I was with a guy and he was blowing on his muffin because it was too hot. And I was like, totally warranted. Blowing in a bathroom. I go in the bathroom like a man.

I blow on the muffin in the bathroom. But it's also when I can eat something too hot. And they're going, how about blowing on something? in your mouth. When you have that piece of pizza, you have the pizza too soon? Yeah. No, that's a problem.

I would never be, if I ever did that in front of a woman, I'd have to disappear for the rest of the week. Remember, John C. Riley, I think. Did you do that? He did something where he was a character and he had glasses and he took a bite of pizza. That's two. And he's like, I don't know the character. I know I'm like looking at him. He had the big poofy hair and the glasses.

I know like the bifocals. Oh my God, that guy's so funny. He's great. But yes. So the other day I got the reverse ick and I'm really proud of it. So you got more attracted to the guy? No, I just reversed the ick. You got the ick and then you.

And then I had some shed at it. Yeah. And then I said, Caitlin, that's a you problem. they're really happy and then I changed it and I was like actually I'm not decked out that was really cute

What was it? Timothy Who I thought the last name was Shamley Shamillay Shalamay Shalamay Shalame

I can't say his name ever And Kylie They were at the next game And he was like Such a fan boy And they started Jumping up and down

together after he got to talk to one of his like idols growing up And they were jumping up and down And I was like Oh and then I was like

Wait they're really happy and she's being so supportive and he was being so cute. He's just like a little kid. So I got the reverse. I was really proud of that. I thought that was growth for me. It is tough to be a man and be just so vulnerably happy. I know. There's nothing. Because it's all we want and then you do it and I'm like, ooh, I can blow your arms like that. Yeah, until they're yours. Until they're your guy and you're like, look at how much happiness he gains from this. But do you think the ick is intuition or is it just immaturity?

The ick to me is a breaking point. I think women more than men are pushed on the dates that they don't want to go on. Yeah. And then they give them a few chances and they go, well, he's got this going for him and that going for him and he checks that box in this box. Fine. I'll go on the date. And you're having just enough fun while you're sitting there wondering what I f*** him. Yeah. And then he takes one bite of a pizza.

And you're like, this guy, this is who I'm out with? This is who I'm trying to. That's so funny to me. That's the ick. Because one man, again, you know, not all icks. To me, the only way the subject is fun and this is if there's retribution, if there's redeemability. Yeah. So my problem is I've been in two days.

different situations where I got the ick like two years into a relationship. I was like, oh, no. And then I've been an other one where it's like, I immediately get the ick and it's a no for me. That's what, I mean, thank goodness. Right. Get it right away. Get it early. Get it early.

Fail early. I would prefer that. Two years in, to me, if you're getting the ick two years in where it's actually affecting you and you don't want to be with your partner. Yeah. That's a turn off. Yeah. Like that's, that's you.

Should that just be acceptable? Because of course people are going to turn you off in a relationship two years. No? Or are they? Is that me? I would hope I would, you know, listen, there are things that my partner could do to turn me off. Yeah. But you go, I love them and I'll look past it. You think the ick is similar to a turnoff? I think a turnoff, an ick is, an ick could be mariable. Okay.

I think a turnoff is, like to me, an ick is like. When should you push past an egg, I guess? I can't tell someone to push past an egg. Oh. I think if some, like, I think it's okay to be to say, I got the ick and I'm out. Yeah. I think it turned off. Like when someone says like my, my ick is dirt under the fingernails, I'm like, that's a turnoff.

No one wants to be with someone who has dirt under their fingernails. Yeah. You know, like, oh, when they're mean to wait staff. That's a turn off. Yeah, that's a turn off. No one wants to be with the person. No one goes, oh, that's just what he does. mean to the wait staff. No, they would be embarrassed of that. Right.

You know, to make it fun, an ink has to be something you go, he wears sandals with jeans. It's kind of not that hot. But I, some women like it. One woman's it because another woman's husband. That's it. Okay, last question I have for you is what is the reveal versus DTR? Ooh. So the reveal is a big part of the book. Okay. So you know how like the define the relationship talk? Yeah. I'm going to have the talk. I'm going to have the talk. I'm going to have the talk. Okay.

The talk is the dumbest thing anyone could ever do. Oh, like the talk, like are we, what are we? What are we? Yeah. The what are we talk. Yeah. The what are we talk. Anytime someone's come to me with the what are we talk, I've been able to wiggle my way out of it.

Yeah. I can wiggle out of a what are we talk easily, which means any man can. Yeah. That's why it doesn't really get you where you want to go. Yeah. The what are we talk, what you want is to not have the what are we talk. we talk totally you want to go hey i've been thinking and the guy go we're together yeah i love you more than anyone on earth yes let's move to the next phase let's put it up on instagram that's that's the

dream yeah that generally doesn't happen if it's on your mind there's a problem right because you don't feel you if you want to have the what are we talk you feel underwhelmed by their care for you yes Just by, in general. I was trying to figure out what would work on me to give an answer to someone wanting to have the what are we talk. And I came up with the reveal. Okay. The reveal, and this is harder to do than it is for me to tell you to do. Okay.

This is easier advice to give than it is to take. Okay. The reveal is, let's say you and I are dating. We're three months in. Okay. Caitlin, I am having such a great time dating you. I'm going to delete the apps so that I can concentrate on whatever this is going to be. You're still on the three months in?

You're just kidding. Okay. Now I just shut up. Okay. And now I say, oh, me do. Whatever you want. You either say, I've already deleted the apps. You say, uh, cool.

Good for you. Good talk. The whole key is saying, I, I, I, and then shutting up. Yes. And then, because if I had someone come to me and say, I'm off the apps, I'm concentrating on what we're doing here. You know me? I don't feel the same way. Well, I would feel awkward.

I'd feel like, oh, God, I'm. It's the talk. I would have to tell you something. So is that the reveal? You've just done the reveal. If someone said that to me, they've revealed where they are. They're not asking for anything. They're not asking for me to give an answer.

And then I would either have to get myself to the same page as them or knowingly live below where they are at. And at that point, I would have to end it or catch up to you. And it's like, so the big thing is it doesn't happen right away. You're not going to get an answer. But you will either be dumped or in a relationship within that week. Yeah. And you'll get the answer that you want from the. What are we talked?

You always make a lot of sense when you talk about relationships. I hope you know that. Thank you. I try my best. You really do. Because I'm not trying to like make someone feel bad. I'm not trying to say like there's a good way or a bad way. I'm just saying this way works.

Yeah. And you know from experience. And now you're happy. And now you've got a book out. So tell everybody where they can find you and your book. I was always, I'm happy to be here. You have been the best. Thank you so much for having me.

I always love hanging with you. Walking Red Flag. That's the book. You can pre-order it. I don't know when this comes out. pre-order it that's very helpful you don't know this as a non-author a non-author i actually do know this because people in my life have written a book but i know how important this is the pre-order's huge you can get an audio book i did the audio book oh yeah i love your voice thank you so if you like

this beautiful voice of mine and your delivery is so funny thank you yeah i was told i just texted with the audiobook director i didn't even know there was a director she was like she was so helpful she was so great uh erica she was like you're funny doing it i was like I didn't think of it that way. So it's... I wouldn't listen to it if it wasn't you doing it. No, it's me. Okay, great.

It's me. I got the first... You can listen to the first seven minutes or something. Yeah. The first 16 minutes on... A little taste. A little taste. A little try.

Yeah. So you can order the audiobook, the Kindle or the hardcover. Amazon, anywhere you get books. I'm doing a book tour. Yay. I'm going to be in Boston, New York. Denver. Jaredfrey.com.

Jaredfree.com. Okay. Great. Philly, D.C. and then my stand-up is different. But the book tour is going to be interactive. You can ask all your dating questions. You can email in with screenshots of anything you're dealing with with dating, and I'll go over it and I'll be as helpful as I can be.

This is so fun. You're so aligned in your life right now, and I'm really feeling it. I love that. You can feel the zen. I feel the zen. I feel the alignment. And I'm really happy for you. And thank you.

Always a blast. Thank you. Welcome to Plutofo. If you know the name of the movie you'd like to see, just stream it for free on Pluto TV. where all your blockbuster favorites are landing all summer long. Catch Anchorman, the legend of Ron Burgundy. Fantastic. Men in black, one through three.

That's what I'm talking about. Mean girls. Side up. Titanic. I'm the key in the world. And so much more. For showtimes, press nothing. They're free 24-7.

That is so fetch. On Pluto TV. Stream now. Pay never. Hi, everyone. I'm hospice nurse Julie, and I have some bad news, but also some good news. Bad news. We're all going to die.

I know. But good news, that might be the best thing to ever happen to your priorities. I've spent years at the bedside and what I've learned is simple. People don't usually regret the big things. They regret the small things. They regret the things they didn't say. Mind you podcast, It's Okay, We're All Gonna Die is where we talk about the stuff everyone avoids. Death, dying, and all of those, we should probably talk about this someday conversations. So if you're looking for something that will help you, check out It's Okay, we're all going to die. gentle reminder that even the hardest topics can bring us closer together. Out now, wherever you get your podcasts. It's okay. We're all going to die. It's okay. We're all going to die. It's okay. We're all going to die.