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I'm so excited to see you tonight. First date, baby. First date. I can't wait. First date.
A
When can you brag as a man?
B
What's up, you guys? As you can hear, my guests won't shut the fuck up. He has a new book coming out. It's called Walking Red flag Advice. Dating advice from your favorite guy friend. Friend.
A
Guy friend.
B
Guy friend. It says favorite guy.
A
All right, I'll take. Yeah, you can be. I can be your favorite guy. Favorite guy friend.
B
Favorite guy friend.
A
Like a guy friend. Like an older brother figure. Younger brother figure who is truthful with you but has give. Will does it while giving you a hug.
B
Who you're hearing right now is Jared Free.
A
Sorry, I.
B
Let's welcome him back. This is your second time on my show.
A
Thank you for having me back. Thank you. It is a pleasure to be here. Some people. Listeners get annoyed if a guy. Like, if someone introduces. Interrupts the host. I feel like we've gotten along.
B
Oh, no, I don't.
A
You let them know that we've gotten along well.
B
Yeah.
A
Just let the listeners know that we like each other.
B
I think everybody knows that.
A
Okay, good. I'm just making sure. Sometimes I see comments and I'm always like, no, we. We had a great time together. I think sometimes the male. When I'm introduced to men, like, I'm usually their girlfriend's favorite comic or like, their girlfriend knows of me and has heard my stuff. And that really offends men who love comedy because they want to be the arbiters of funny.
B
But it's like, too bad, right?
A
I agree. I think that's like a real, like, small dude move to be angry that you're like, also, it's your girlfriend. Take some interest in her. Like, she says she likes this guy. Why don't you, like, have a little curiosity? Yeah, I just. I get. And then they come to the show and they're like, oh, dude. And I'm like, nice to meet you, man. We're a lot alike. There's a reason your girlfriend likes me. She likes you. I don't know, I always, I feel defensive about it. Probably that's okay.
B
But that's why you're everyone's favorite guy friend. Friend.
A
Favorite guy friend, Favorite guy to women. I, I, you know, I try to be truthful about dating and I think a lot of men hear like my dating advice stuff and they're like, yeah, that's exactly what I think.
B
What's like your number one piece of dating advice?
A
You're not confused, you're turned off. I think a lot of women like to say. I hear women, smart women, talk about how confused they are. College educated women are like, I just don't know what's going on here. And I'm like, you do know what's going on here. You have permission to be turned off. And I think women a lot of times need to, like, need 17 reasons to dump a guy who's a good guy. And because they're told, go out, go out with him, try, give him a shot. Men aren't really told that, you know, Like I, men go on dates with women they're attracted to or they don't go out at all. Women go out with guys that they have no attraction to because a friend was like, he's great. And then they go like, that's the most crazy thing that is kind of
B
insane to think about.
A
It's true, though.
B
Yeah, right?
A
How many times were you pushed on a dates when you were single? Like, go, he's great. You know that gets told you all the time and it's like, and then, then they go, and then they go. Well, they feel like it's almost like they have to build a case to this female tribunal to tell them why they don't want to go out with a guy anymore. And it's like, no, you're not confused. You're not, you're turned off, you don't like him, move on.
B
I feel like there's more drama in a breakup though, because in a breakup, a girl will have so much trouble breaking up with a guy and she'll need 17 reasons to break up.
A
How so? Explain that, please.
B
So usually a girl will stay in a relationship until a guy does something really bad, like cheat on her.
A
Right.
B
Or something like that.
A
Well, you know, because women will try and try and try again with someone who is a red flag is not treating them right.
B
Right.
A
Men will break up before the next step. Like when I broke up with women, it was always before it became more serious. Like, that's why I always say, beware of birthdays, vacations New Year's, Valentine's Day, global pandemics. Because all those are good reasons to end things. And when. That's when guys end things.
B
Yeah.
A
They get enough separation or space, or this big thing is going to come up that will inherently like Valentine's Day, whether you believe in it or not, in inherently makes you more of a couple than you were before Valentine's Day. So if you start dating someone on February 1st, you really only have 13 days before it gets more serious, because
B
then you've spent a holiday together, you've done something together.
A
Just acknowledgement of the day alone is making you closer than you were on the 13th of February. So a birthday, same thing. Hey, let's go out for your birthday. That's you two getting to know each other, getting a little closer. You can't be as casual as you were the day before. So men end things before those dates or right after them. They freak out. They go, oh, my God, I'm in something serious. I got to get out.
B
It was too much.
A
It's too much for me. Even without the woman asking for anything. So many women that write into me in the podcast, in the book, they'll always be like, I didn't. I didn't say I want to get married. They always say that. It wasn't like I wanted to get married. Well, you do at some point. So these guys are getting ahead. They're, you know, they're. They're making sure this is the one time they've ever been prepared. They're preparing themselves to dump you. And they're doing a little earlier than they would have. I'm just saying. So I think the biggest thing for women that I get questions on is, like, can I? They're looking for permission, and I don't think you need permission to be turned off.
B
I agree. Well, last time you were on my show, you were single.
A
I was.
B
Was. So you're. You're in a relationship now?
A
I am in a. I'm in love. I'm in love. I don't care who hears it. I'm in love.
B
Where did you meet her?
A
So, I mean, this is a story that nobody should take any lessons from.
B
Do not try this at home.
A
Don't try this at all.
B
Done by professionals only.
A
You're totally correct. That is a great way to put it. We met at a show. You know, Modi, the comedian. Modi was up at the Comedy Cellar. He's on stage. He was getting heckled. He's, like, trashing this heckler. And there's A woman in the front who's dying, laughing at him, making fun of the heckler. And then he says, the next comic is single and Jewish. You'll love him.
B
And everyone was like, jared.
A
And then, Jared, Jared. And then the horror started playing Hava Nagi la Ha. And then that's my entrance music at the Cellar. They start playing it. Chairs. Everyone's lifting a grandma on a chair.
B
I love this.
A
And then I come on stage and we have like this brief interaction. I do my set. I don't really remember the set. She doesn't either. And then we started interacting via. He posted the clip of trashing the heckler. See these, these crowd work clips. They're working the crowd.
B
I love crowd work clips.
A
So then it was like, that was like our beacon to be able. That was our. That was our lighthouse.
B
So you guys started talking in the comments on Instagram a little bit.
A
You know, in dm, we found each other through.
B
That was heckling. Was she laughing at your stuff when you were on stage? Do you remember?
A
Come on.
B
Okay, hold on.
A
Let me rewind that question. Laugh at my stuff. Did you notice you're talking to Jared Funny man freed, the wizard of Haas. Of course she's laughing. I'm the wizard casting my spells.
B
Do you remember her from your set? From being on stage?
A
I remember. So I remember her from being on stage. And then I. And then we ended up. Nothing happened because I think we were both being a little cool about it. We ended up matching on Hinge, like, a month later, restarting the conversation. So then we go on a date.
B
You know how wild that is to meet her on Hinge, like, randomly in the world full of people.
A
It's. This whole story's wild. Like, we. It is wild. I, I think we were. I, I really do have these moments where I'm like, and I don't mean to sound like woo, woo. I, I do have a crystal up my ass, but only for pleasure. And I, I, I really do feel like we were meant for one another. Like, the world kept pushing us together.
B
Yeah. And so you had the. So you noticed her while you were performing. You matched on hinge and you started kind of lightly talking.
A
So we go on a date. We had what I would consider one of my best first dates. Like, had this, like, really great first date. And I remember she was wearing a ribbed skirt. It was like a sweater skirt. Ribbed. I remember she's curvy and like, so my type, like, I'm sweating her. And then we walked her to oh
B
I haven't heard that term in forever.
A
I love that.
B
Yeah, I love that term.
A
Oh, my. Because I. What? That's the only way to describe it. And where'd you go? We went to this place. I think it's closed now. It's a wine bar. It's right. It's in the West Village. A wine bar in the West Village.
B
Okay.
A
They do, like, wine and cheese stuff. I think they've closed. And it's. And I wish I had the name, but. But I walked her to Rosemary's, which is in the West Village as well. That, like, Rosemary's has been there forever. And I remember it started raining. We had a kiss, and then we started to kind of talk from there. And I wasn't really in the place of dating, you know, Like, I was d. I was trying to date, but I could feel I just wasn't doing it. I was. I was. I. You know, I felt I was serious. I think a lot of men feel this way where they're like, in the moment. You're like. And then you look back, you go, I. I'm more serious now. You know, obviously, like, how I act now. This was two and a half years
B
ago that you met her?
A
Yeah. So this story is from two and a half years ago. We go on dates, we end up dating for a few months.
B
I haven't seen you in that long.
A
It's been a bit. That was when my last special came out. I. And I had a special coming out. I was distracted by that. I mean, there's a million excuses. The real answer, and I think the answer for a lot of men generally, but I'll speak for myself, and I think I'm 10% away from most men. I didn't have the confidence to push forward. Like, I've told her, I go, I wish I was more confident. I wish I had the ability then that I didn't have. And I ended it. I remember ending it.
B
You've broken up with her?
A
I broke up with her. She was like. She didn't say, you know, she was like, you got my number. She kind of played it that way. And we.
B
Why did you break up with her?
A
I. Again, I told you, I didn't have the. I think. I don't know. I didn't have the confidence. I really do believe it was a confidence thing. Like, I. I didn't believe in, you know. You know, there's a million things that anyone could call me out on and be like, you're bullshitting. But, like, I think this is very. You know when it comes to career and am I enough and do am I ready? And again, I don't think age even plays into that. I think where I was at the time, I just wasn't there. Welcome to the Mystery Boys. I'm Kermes Trez Whiteclawsmith Dunstan Trudeau. We're here to gape your fourth eye, Three Eye Atlas, JFK's Dr. Hamas, Hitler's Dr. MK Ultra, Adrena Crumb, Alistair Crowley. You ain't heard the Mystery Boys get the bottom of it. I didn't see one dick in those catacombs and I looked everywhere. Well, this is the show guys. I hope that your mom's house is happy.
B
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A
It was like three to four months of, like, not that long, but not that long. It wasn't like two years. We weren't, like, together. We were like. I knew I had to, like, either be together or end it right. You know, that's. To me, that's a version of respect. Is like, I'm ending this to let you go and to let me go into. Not with this. And I'm making a decision. A decision is respect.
B
Yeah, I agree. I totally agree.
A
So I ended it. And I remember her, like, seeing her for the last time, and that was. And I, you know, Instagram stories. I would see her watch my stories, and I would watch her. She didn't post a lot.
B
And I called orbiting.
A
Is that what it's called?
B
It's called orbiting. When you don't want to be with someone, you're unsure. Like, you're not together, but you have some level of interest enough to kind of want to know what they're up to. And then when you check to see who's looking at you, you're somewhere subconsciously looking to see if she's watched you.
A
Right. That's why when someone says social media is stupid, I think that that is an opinion. They're trying to take the. They're trying to. They're trying to, like, make. Disregard your feelings. Like, they're trying to, like, social media is important because everything's important. Everything's. Everything exists in this world could be important, you know, so when someone's like, oh, you're talking about social media. You're making too much of it. No, no, no. I'm making what I make of it. And that's my emotional choice. And you can't tell someone how to feel. But I remember seeing her watch my stories, and I'd be, like, affected by it.
B
Yeah.
A
And then. But then I would say, jared, no, I'm. I don't want to, like, go back and then not be excited about it and go through a. Another break. I was afraid of, like, what if I go back and now I'm not ready again.
B
Yeah.
A
And so this hap. There's two and a half years, and I kept making deals with myself. I'm like, I'll reach out if I'm still thinking about them. Then I'll reach out and I'll do it then and I'll do it here or I'll do it there. And if I'm still thinking of it, there's. And then she reached. And then I was going to Philly to do a show and I, she reached out to me. She was like, I keep getting your targeted ads. And I know this is crazy, like, thank goodness for social media at that point. And I was like, she was like, would you want to get coffee? And we got coffee.
B
What are your targeted. What are your ads?
A
My ads were targeted at curvy women with fun personalities who I.
B
To come to your shows.
A
Yeah, that's, that's what I put in under the. I'm like, hey, women who would look good in a rib skirt. That's who I want at my show. That's why I'm like meta curvy Jewish woman who like to blow men. Put that in. That's how I would target the ads.
B
It worked.
A
And now. So then we went and got, we didn't do other show. The next after my show, got coffee and I, I kind of confessed all this to her. And then I had this book that I was writing. In the two years that we were broken up, I had this book and there's stories in the book about her. And I was like, I had to be like, and by the way, you're in my book. You're in my book. And she's like, I gotta read it. And she read it and she was like, there's three stories about us. And I was like, yeah, wow. And it's been, you know, so now the book. And so now we started dating and we're together and now she's gonna move down to Florida where I live, and we're moving in together.
B
And so how long have you guys been together since then?
A
Six months almost.
B
Cool. Yeah, that's a good amount of time.
A
I, it, I, you know, it's, I was, I'm just excited, you know, and that's all I wanted when I was dating. I think, I think excitement is underrated in these times. I think especially as you get older, you start saying, and the book is all about this. The book is about like letting yourself. There has to be a mix, you know, relationships are a mix of a big frappuccino of delusion and logistics. Logic, Logic and delusion. You have to be a little delusional. You have to be a little woo woo. You got to be a little bit where I'm at right now. You also have to be logical, you know, like, you got to talk about finances. You got to talk about where do we see ourselves living, and do I like you and do you like me and what do you. You know, all those things. So you have to have difficult conversations, but it's a mix. So, like, you know, I always was. The one thing I've always said is, I want to be excited. And I was all, you know, you question whether you can get excited. You know, if you're single, you're like, I don't get excited about anybody. I used to always say that. I'm like, I've never wanted to make a friend ever. And. And now I believe at 41, I'm gonna make a best friend. Like, I avoid everyone, so. And it's been fun to get to know each other now. And it's. It's a little weird because, like, this gap of time, like, I did feel like she was with me.
B
That's so. That's so serendipitous, kind of.
A
Right. There's two ways to look at it. You know, I've had people be like, what? You know. You know, you get hard questions. You know that you can. If you. If you. If you come across a miserable person, they're going to ask miserable questions.
B
Is she Jewish?
A
Yeah.
B
I remember asking you that the last time you were here. I was like, is it important to you that the girl you date is Jewish? And you said, yes, it's.
A
It's important. Yeah, I. Because I. You know, her and I share a lot. Like, we're very much alike. We're very much. And. And a lot of this stuff. That's why, like, moving in quick. Like, I know her.
B
Yeah.
A
You know, I think that that stuff, to me, is important. I didn't want to have to, like, explain what summer camp was like. I, Like, I. I didn't want to have to, like, explain Rosh Hashanah. I don't. I don't even know what the fuck that is. I just know I have to go and I have to wear a suit that doesn't fit because over the summer, I ate like a pig. So, like, I. And, like, I like that she relates to that. Like, nothing worse than going to temple to Rosh Hashanah and having to go back into your temple clothes after a summer. Like, she relates to that, too. So, like, yeah, those are things that are small but do feel familial. I was looking for someone that would feel like family, and she's come down to Florida. My Parents live in Boca. I live near my parents in Delray beach. And like, she's in with the crew. Like, it's fun.
B
So you got together like six months ago, which means. Did you guys spend Christmas together?
A
What's Christmas? Oh, no, I'm kidding. Yeah, no, no, we did. I, we missed that. It was after New Year's. Oh, it was after New Year's. I was coming back from San Diego. I was doing New Year's week. Okay, San Diego. And I was like, you had Valentine's Day. Random text. We had Valentine's Day. We went, oh, come on. I do it all.
B
What'd you do for Valentine's Day?
A
Carbone, baby. Talking to the wizard.
B
Aha. Car bonus.
A
You're talking to the wizard of rigatoni here.
B
Legit Carbone.
A
I got it from a buddy, got me in and then I had a show in New York.
B
How fun.
A
So then she got to watch me perform for an hour.
B
Yeah, well, she thinks you're funny anyway.
A
I hope so. She better.
B
She's stuck with you now.
A
What if she cast my spell on her?
B
Wealth management so she can be anywhere
A
and do that anywhere. That was, that's another thing. Like again, logistics versus romantic. Like, we can our work kind of. And I also was like, listen, if, if, if I, I'm up. The one thing is, here's the thing about 41 and in a relationship now, this is like my second marriage. I, to say that someone who's 41 is in their first marriage or first relationship or first. It's not true. I have learned from if, if you're 41 and you're making the mistakes of a 27 year old, I, I, I don't think you should be dating that person. Like, I, I, I, I know too much about myself and I know too much. Maybe because I've had a dating podcast for all these years, but like, I just, you know, the idea of like, well, I don't know how I'm gonna talk about finances. I was like, how much do you pay in rent? Like, I, that's a question I couldn't ask my 20s or I didn't know how to ask, or should we have a joint account? Do you want to, how do you want to do money? Like, just even saying that, like, I, I don't know if I would have had the ability. So I can't Talk on a 27 year old because that's hard to do at a certain age. But then you get older. It's like my second marriage. I don't think I would be as bad at it. Like, so I've learned. So. Yeah, I, Yeah.
B
So now she's moving down to Florida with you.
A
That's right.
B
And you guys are going to live happily ever after.
A
We hope that's the, that's the goal. I mean, I, I don't like to say yes, we hope, we hope. You know, you never know what happens. But I, I'm optimistic. I'm, I'm excited.
B
I think it sounds like you have confidence.
A
I've, I've gained some confidence. I, you know, I don't drink anymore. That helps. I, you know, I was like trying to take away all these variables in my life.
B
What are your vices? Do you have any vices?
A
Coffee. I drink like 30 coffees a day.
B
It's a good thing you're not able to get pregnant.
A
You can only have one, one a day.
B
You can only have like 200 milligrams of caffeine.
A
I just don't know how to keep. I have like a hand to mouth thing that I like, you know, I just don't know how to like, like I have to have something going on. So a coffee is really just to like lift it and put it down.
B
Yeah.
A
You know, it's like I, So the vice stuff, like I like to eat, I do that. I go to a lot of restaurants and I like make videos from there. I like making videos from restaurants. They drive me crazy. But I, because all the comments are like, you should have gone here. And it's like, I didn't make a video to get a fucking recommendation. Like, what kind of crazy person, hey, this food's delicious. Well, you should have gone to this area. Isn't that a miserable fuck? Yeah, like that's how you talk to people.
B
Yeah. You're like, I'm trying to tell you what's good.
A
And keep scrolling. Leave shoe.
B
People can't do that.
A
No, they can't. And then they, you know, I don't know, we become faceless nothings. Like, I don't know, like go here. Like, I don't know, like I made a funny food video. How about you like have like, oh, this is fun. That's what I would. If I watched the whole video, I wouldn't go, like, I would just go, this is fun.
B
I see what you're saying.
A
Like, I just don't. So I feel like on Tik Tok, the, the, the quote creators, the comedians become faceless to the people watching and, and to me too. I watch them. I just keep going, you know, I'm like, who's this loser? You know?
B
Do you like to cook?
A
Yeah. Yes. But, like, I. I should take more. I. I would like to take more of an interest in cooking. But the problem is I'm in an apartment building. The grill is downstairs. So I have to, like, go downstairs and then bring all this stuff. Like, I. I'm so lazy.
B
I like the grill.
A
I. I would like to grill. That's what I would want to do if I cooked. Do you cook?
B
I do cook.
A
What do you make? What's your go to?
B
My favorite thing to make is pasta.
A
Give me the pasta.
B
Oh, I mean any kind of pasta. I have a pasta maker.
A
Oh, you make like, homemade pasta?
B
I make homemade pasta. I make pasta from scratch.
A
That's like real deal.
B
It's so easy.
A
So you're like a nona. You're like.
B
Yes. I lived in Italy, though, for like a year, and I lived with a family back when. In my early 20s. Early 20s. Like 22.
A
What made you do that?
B
A guy. I met a guy there.
A
For a guy.
B
I met a guy in Las Vegas when I was like, 22, and he was Italian, and he was from Italy, and he was spending three months in California and he was staying in San Diego and I was staying, like, closer up towards la.
A
Yeah.
B
And so he was there for three months, but we met in Las Vegas and we dated for the three months. He didn't speak any English.
A
So what did you connect on?
B
We translated on phones and I started to learn.
A
How year was this?
B
This was so long. This was like, how. Oh, my God. It's so embarrassing how old I am now.
A
You can get older.
B
It was like. It was like a long, long time ago. Okay, A long, long time ago.
A
How old are you?
B
I'm 38.
A
I'm 41. What does that say about me?
B
But I met him when I was like, 22.
A
22. So you were doing, like, Google Translate.
B
Yeah, we were translating how to speak to each other.
A
He been so hot. Like, I. That doesn't happen.
B
I thought he was.
A
You weren't like, well, he seems funny. You couldn't understand a word he said.
B
He was funny.
A
I'm sure he was hilarious.
B
It was great.
A
I'm sure. I'm sure when you did the read out loud on Google Translate, that's what she said. He's hilarious. Oh, Emilio. Oh, Luciano, you're hilarious. While he washes abs.
B
Oh, my God.
A
Oh, Luciano. Oh, Luigi. He's funny. You're saying that to the guy, like the comedian on stage. He's Funny. You should hear him Google Translate.
B
That'd be terrible. Yeah, I would never.
A
That would ruin me. I would literally go in the back and cry. Like this guy with this hot chick in Vegas couldn't even speak English. I'm in Vegas, like sweating outside of a club, hoping to get in the pool party and hoping that the whole group decides to keep their shirts.
B
I have to tell you that I make pasta.
A
Yeah. And then I made it about me at a pool party with my shirt on in the pool party.
B
He didn't even have a great body.
A
Stop it.
B
He didn't. I was also. He was also my height.
A
What is that? How old?
B
5 4.
A
So you went out with a 5 4? Chubby. He wasn't chubby.
B
He was not chubby.
A
But he didn't have wash borax. Chubby just took offense.
B
He just looked like me. He just like. He looked like me with brown hair.
A
He looked like you.
B
Hold on, I'm trying to say he
A
was like, we're finding out your kink. He looked just like me with brown hair.
B
I mean that. He was like my size. He was my size.
A
Was that your type?
B
No, but that's just like what I found in Vegas.
A
You're talking about him like, like he's a rare laboo boo. Just what I found in Vegas.
B
Just. He was there.
A
Find him anywhere.
B
He was at the. The Excess Encore. Excess. Wherever that was. I remember those parties and I was just like at a party and he was there and I can't say we
A
started talking and then he taught you how to make pasta in Italy. How was the year? How was the year living? Did he live with his parents?
B
He, he, well, he. Yes.
A
Yeah. Because the Italians, they're very. I mean, not just Jersey Italians, but
B
like, they're very family oriented.
A
Well, they're cheap.
B
But he had a big house, okay? And it had like apartments in this house.
A
Like I had a piazza and had a.
B
Like it was not quite a piazza, but they, they were well off.
A
Okay, and so now we're starting to understand.
B
He had his own.
A
How he got of this house, okay? Now he didn't have to be good looking or funny. He was rich.
B
He wasn't rich.
A
You just said he was well off.
B
He was well off, but he wasn't rich.
A
I think he do.
B
While he was here, he was a car mechanic for Ferrari.
A
That's like. Is he a cartoon of an Italian person?
B
But he was a car mechanic.
A
Yeah, no good for him. I mean, but high end cars.
B
For high end cars.
A
What's the richest guy you've ever dated.
B
The one I'm with now, right now. Yeah.
A
Billionaire or millionaire?
B
He is a strong millionaire.
A
So 500 million above or below.
B
I cannot talk to you about this. Be so mad, like.
A
Told you how real estate or finance?
B
He owns Terry Blacks and Black Family Hospitality. They have five locations. They've opened four new restaurants in the last, like, couple of months.
A
That's 500 million.
B
They're opening three hotels.
A
Hotels. I didn't even know he was going that way.
B
Terry Blacks, they're opening three bath houses.
A
Bath houses.
B
Have you ever been to ancient air baths?
A
I know that that's, like, a thing that's, like, happening right now. Yeah, bath houses are, like.
B
They're, like, making their way.
A
What's the one in New York?
B
Ancient air baths.
A
But there's another one.
B
There's one in, like.
A
I don't know if. I don't know if I want barbecue while I'm in the. In the bath house.
B
What a better time to detox.
A
I mean. Yeah, you go in there for your meat sweats. Is that, like, the plan?
B
That's what I think is funny about it, right?
A
That is funny. I don't know. I'd be farting everywhere.
B
It's okay. Just say it was the steam. Be like, man, this place stinks.
A
So, wow, Terry. I think I went last time I was here. I might have made a video.
B
Oh, yeah.
A
Maybe he commented. You should have gone to our other location. No, I like it. It's very good.
B
It's a good restaurant.
A
It's a good restaurant. So they have three here.
B
They have one in Waco, one in Lockhart, one in Austin.
A
Is he Terry?
B
No, his dad is.
A
His dad's Terry.
B
He opened the restaurant after his dad. What?
A
Nepo baby, you gotta.
B
What's that mean?
A
You don't know what a Nepo baby is?
B
I don't know.
A
You have no idea what.
B
I don't know what a nepo.
A
You live a nepotism baby.
B
What does that mean?
A
Means you got your money from your parents.
B
No, he didn't.
A
He didn't. But his dad's Terry.
B
So you want me to tell you the story very quickly, what happened?
A
Yeah.
B
Okay. So Terry has a brother named Kent, and they owned Black's Barbecue. Their parents owned Black's Barbecue. Okay, well, Kent became a lawyer, and when their dad was dying, he had his dad sign over basically everything in the will to Kent.
A
This is, like, the most Texas thing to ever happen. Yeah. It just feels like. And. And we went on a grand Adventure to find Terry Black's recipe hidden in them hills out there. And when we found the legend of Terry Black's bacon, we became billionaires.
B
I think I like your story better than that. Right.
A
It would be fun. And you have a guy with a prospector with, like, a big hat on. And he's like.
B
He's like, oh, my God.
A
You know, he does one of those.
B
That sounds scary.
A
Okay, I won't go scary. So now you're. You have the child of.
B
Wait. I have to finish the story.
A
I'm sorry. Okay.
B
Without the gremlin.
A
I'm sorry. It wasn't a gremlin. It was a prospector who was laughing at you as you went up the mountains to go try and find bacon. The secret bacon recipe.
B
Yeah.
A
The secret Black family.
B
That story developed.
A
I. Listen, I got it up here. Option it.
B
Fascinating.
A
Okay. If any. Any Hollywoods watching or listening.
B
So the brother.
A
If. If Mr. Segura's watching, I'm never gonna finish this. Maybe he'll put some money into my project.
B
You know what? There's two people listening that care about this story that you're not letting me finish.
A
It's Terry in black. Go on. I'm sorry.
B
Do you guys think I'll get through this story?
A
Yes. I'm listening.
B
Okay. Well, you can't shut the fuck up.
A
I know.
B
So I'm just wondering.
A
That's a fair feedback.
B
So the brother. So the dad. So the grandpa dies. The brother takes over the whole business. It fires Terry gone from Black's Barbecue. And then he was also in, like, what is accounting? So he just did accounting and for, like, the next. I don't know how many years. But they were not in the barbecue industry anymore.
A
Yeah.
B
Because the brother had taken the business. So Mark, my husband, and his twin brother Mike, and they have a sister named Christina. They all decided to start a restaurant in Austin and name it Terry Blacks because the original is called Black's Barbecue. And they couldn't name it Black Barbecue.
A
Did they have the recipes or they
B
just knew how everything they have is different than Black's Barbecue.
A
And they probably. The timing was probably perfect. Austin's growing.
B
They really hit the location.
A
Right.
B
Like, the perfect location at the perfect time.
A
I like that story.
B
And so they named it after.
A
Think it needs a prospector.
B
Oh, my gosh.
A
I think it needs a little bit of a treasure map.
B
Not even any bacon.
A
Okay. Yeah. They. We could add bacon to the menu. Are they looking for new menu items? No, I like a big slab of bacon.
B
We could Throw some bacon in the Mac and cheese. That sounds good.
A
That'd be pretty great. I don't. Mac and cheese. You like bacon in it.
B
I. I like bacon in pretty much everything.
A
I agree with you. I. Lobster Mac and cheese bothers me. I don't like it.
B
I don't like it either.
A
It feels like it's a marketing thing to get people to spend more money on lack of.
B
Have you ever had a good lobster Mac and cheese?
A
No. And I think. I actually think less of someone who would like lobster Mac and cheese. I've done.
B
Do you like garlic mashed potatoes or regular?
A
I'm okay with either. Matt, I think any day you're eating mashed potatoes is a good day, but also a sad day.
B
I like pureed potatoes.
A
I do, too.
B
But I don't like garlic. You don't like the garlic and I love garlic.
A
I think it's got to be. I gotta taste it. I. I mean, it would be depending.
B
Too bad they can't bring you a little spoon.
A
A little spoon. What I would do. I think that's a great idea. Now. Now we're talking. Hey, Terry Blacks, get a spoon of mashed potato while you wait in that line.
B
Yeah.
A
Wouldn't you like a little spoonful?
B
Yeah.
A
Good merch right there. Wouldn't you like a little spoonful? Put that on a hat. I'm like a walking shark tank over here. I'm a merch machine. Jared. Merch machine Freed can be seen on the road. Go to jaredfreed.com for tickets. We'll be right back. I got to say, Tom Segura or the YMH, you know, CEOs, whoever they may be taking care of the people here. The bathroom, great toilet paper.
B
You like it?
A
That is way more than they had to do. I just think the listeners need to know.
B
What kind of toilet paper is it?
A
It was like multiple ply. Like, this wasn't office toilet paper. Do you guys appreciate how well you're being treated here?
B
What kind of toilet paper do you buy at home?
A
I get the nicest. But that's why when I go to an office, I don't expect.
B
But is that Charmin.
A
Whatever that is in that bathroom is more than Tom had to do. I'm no corporate shill, but I'll tell you right now, when I sat down to take a dump and I took a look to my left, I was like, tom Segura is doing pretty good by these people. Look at him. And then they had wet wipes.
B
Hardcore.
A
That's a. I Mean wet wipes at the office. You don't expect that. That's kind of awkward, don't you think?
B
How kind.
A
It's kind, but it's like every time you see your boss, like, you're like, he was thinking of you having a wet wipe for your ass. Isn't that kind of weird? Well, I was thinking about that. I was taking a Here.
B
I think you can overthink anything, Jared.
A
I overthink everything. I mean, that's why I'm here right now. I overthink literally everything. But I. I was. I go, wow, that's really nice toilet paper. And then I saw the wet wipes, and I was like, what. What is this?
B
Were you torn between which one to use?
A
No, you use the wet wipes first and then one slice of the good
B
toilet paper, like, one square.
A
Well, you don't have to use as much because you've cleaned up with the wet wipe.
B
How in the world.
A
How do you wipe.
B
I shake a ton of toilet paper, and I wad it all up in a ball, and then I just dab myself and I'm done.
A
That was someone's wet dream just now. They've been waiting for someone to ask you that question for 100 years. There's someone who's the creepiest fan you have. I was like, oh, rewinding that thousands of times.
B
My husband hates how much toilet paper I use.
A
Really?
B
He thinks it's so wasteful.
A
So you w. So much.
B
I don't want it to touch me that my, like, you know, I want, like, a nice puffy ball.
A
I, I. Yeah, that's too much for me. I like to. I like to have control. I like my. My toilet paper is like a sports car. I want to be able to move it around my toas left and right.
B
I need to have an easy, like, you know what, Like a loofah looks like.
A
I know. I. I know. You don't even have to explain anymore. I totally understand what you're doing, and I agree with your husband. I think you're using way too much toilet.
B
Yeah, we go through so much, you clog the toilet. I don't clog the toilet, but I use a lot of toilet paper.
A
Well, that's what causes the clog.
B
Mmm. Is it?
A
I. I take a huge dump. I don't clog because no tp.
B
You should see how much toilet paper I use.
A
You're using a lot.
B
Yeah.
A
Yeah. I don't know if your husband can afford it. Good thing he's got a lot of money. Could you imagine what if he went out of. What if he was like. Terry Black says we have to close the location. We're using too much toilet paper at home. We gotta close.
B
My world will come crumbling down.
A
Yeah, sorry, Waco, it's over for you.
B
If she doesn't relax with the toilet paper, we're all going under.
A
Yeah, tell her to chill. That's great. I'm happy for you. So two kids, you think you'll stop at two?
B
I might.
A
Okay.
B
I don't know. I have to see how it goes, right?
A
How do you like having one?
B
I love it.
A
You love it?
B
I love it.
A
It's fun.
B
It's super fun.
A
When did it get fun?
B
Yesterday.
A
Yesterday?
B
Two days ago. Two days ago.
A
That's it. Because when they. I see people with babies and it's a little mush comes out.
B
What's today? Friday.
A
Friday.
B
It got fun on Tuesday. Tuesday.
A
So Tuesday you literally said yourself, you go, wow.
B
I can show you the text message that I sent my husband and I said, this is the moment I've been waiting for.
A
Give me. And you said, 15 months before. So what was the moment?
B
So we moved from two naps to one nap, which is huge. It's a huge thing. I wouldn't know with little kids.
A
If I knew that, that'd be weird, dude, single guy, no kids. Oh, yeah, I heard when you move from two to one, it's like, if I knew that, you'd be like, get rid of this.
B
Trust me, the difference is massive. Because when they take one nap, kind of like in the mid morning and one nap in the afternoon, you can't do during the day.
A
You're caught between a rock and you've
B
got like breakfast nap, lunch nap, dinner, bed. And it's like, that's your day.
A
Right.
B
And so in between are like these spurts of playtime. But when they move to one nap, they can have like breakfast, lunch and a nap. And then they get like five hours to go do an activity. So we've been going to playgrounds, took them to a water park. We've been like going and doing stuff.
A
I don't mean to call you a liar, but you said you, he has $500 million.
B
I didn't say that.
A
He has never said that. Okay, you didn't say that. I. I just took that away. Where's the nanny?
B
My mom. My mom lives with me.
A
Your mom lives with you? This guy don't got 4 million.
B
I requested this.
A
Really?
B
Yes.
A
Did she move here?
B
Yes. From Pennsylvania.
A
From Pennsylvania. How does he feel? About that.
B
He loves her.
A
He loves her because she takes a lot of the attention off of him.
B
And she has her own wing of the house.
A
A wing? Like she's living in Italy with some guy she met.
B
Yeah.
A
That's crazy.
B
And she's so helpful. So, like, right now she's just hanging out with my son and it's someone that I know.
A
Do you guys get along?
B
Yeah.
A
You and your mom?
B
Yeah.
A
That's nice. And you all get along? You guys all.
B
Yeah.
A
Break bread at night and have dinner
B
and we don't really eat together. I wish we did, but our. Our eating schedules are off.
A
It's gotta be tough for the restaurant tour. Yeah. I try not to eat with my mom because she goes, what are you eating? You don't need it. Really don't need it. Yeah. That's all my family talks about is my body. They're obsessed with my body. I wish a woman would be as obsessed with my body as my parents are.
B
Yeah.
A
Yeah. So every dinner I'll be eating and they'll go, you're not done. You're still eating. Can you imagine? Everyone eat. You're gonna eat. It's gonna get cold. Then you start eating. You're still eating. That's every meal.
B
Damn.
A
We went to a great place in Fort Lauderdale the other night called Mortarano's. If you want to look up a place, if you want a group dinner, if you're looking to go to Fort Lauderdale and have an amazing time, go to Mortarano.
B
I am going to Florida soon, in like the next month. But I'm going to a place called A3.
A
A3. Have you ever got a highway exit?
B
I don't know.
A
Where is it in Miami?
B
I don't. I don't even know.
A
I'm. I'm in Del Rey.
B
I just saw that it's a section of the beach called A3.
A
I know nothing of this. Oh, that must be like a pregnant woman area. I'm in the cool no kids area.
B
Oh, that must be what it is because I'm in the cool kids centric area.
A
Yeah, I'm in the cool 41 year old.
B
Are you gonna have kids?
A
I would love to. I gotta see what the next episode's like. I'm living in repeats, you know, I think it's fun to see what's next, selfishly. And I think I'd be a fun dad. I'd be annoying.
B
Oh, my God, you'd be the best.
A
Thank you. I think I'd be fun and annoying as a dad.
B
Like, does exactly what you have to be.
A
That's my job. Right. I think I was built for this. I have a. Like, I had a dad bod before even having kids.
B
You're already.
A
I'm already there. I'm already the shape. I. I love fucking with idiots. That's what a kid is with it all day. I like bothering my girlfriend and like, making jokes and getting her to laugh. So that, I think is built into the.
B
You would have so much new material.
A
Yeah, the material that. I don't know. I. I. Yeah. I just don't want to do that.
B
You wouldn't. But you would.
A
I hope so. Again, hopeful. I can't say definitely.
B
Are there any. Would you prefer a boy or a girl?
A
My dad's convinced my brother and I are gonna have girls no matter what.
B
Are there any girl names you like?
A
I don't know. I've never thought about it. What do you like as a girl name?
B
Zoe.
A
Zoe. How do you spell it?
B
Z, O, E?
A
No, no. Um. Lot.
B
Is that a Y?
A
That's like a. Two dots over the E. No. Do people do that? I don't know.
B
No one does that.
A
I know. It's a German thing. Oh, it is. I knew.
B
Oh, then maybe I will do it. My husband's part German.
A
Okay. If you have a girl.
B
If I have a girl. But I'm having another boy.
A
Right? You told me.
B
Yeah.
A
And what's the first boy's name?
B
Jax.
A
Jax?
B
Jax.
A
Very Texas, very. Not Jewish.
B
Yeah.
A
Putting an S at the end of Jack.
B
It's Jax.
A
Jx. Oh, my God. Does he already have a tattoo?
B
Not yet.
A
He's getting a tattoo right on his forehead. He's getting it everywhere. Under the lip?
B
No.
A
Jax.
B
Jax.
A
After the guy from Vanderbump.
B
What? I've never seen Vanderbump Taylor.
A
He was like the villain. He was like the.
B
I'm glad I didn't see it impaired my decision making. But, you know, I'll tell you, I don't have a name picked out for the second one yet. And what's weird about picking out names is, especially for me, picking out another boy name, because my husband picked it the first time, and I've never dated a Jax. I've never even known a Jax. So, like, I had nothing against a Jax, but now when I start thinking of names and we're, like, brainstorming names, my husband will be like, what about this name? What about this name?
A
What about Luciano? You'll be like, no, I met him in Vegas.
B
He looked like me, but he's like, what about Connor? I'm like, no, dated a Connor.
A
What about.
B
Like, what about.
A
What about.
B
I don't know, any. Whoever. Nate? And I'm like, nope, I've dated a Nate.
A
You dated Nate Bargazzi?
B
No. Shut up.
A
Sorry.
B
But you know what I mean, like, it's crazy how.
A
No, no, I. The relation of, like, it is one of those weird. It's like, it's one of those weird word association games.
B
Yeah.
A
That you can't really avoid. And it's like, you know, like, even I. I don't know if my mind would go to person I dated, but it might go to, like, what I feel about that person who had that name.
B
Yeah.
A
You know, like, I. I guess that's a similar thing, but I'm saying, like, I just. Like. Like, I mean, there's. I mean, the thing right now is, like, will anyone ever be named Karen again? Like, is that name gone?
B
Yeah.
A
Who would even dare? I mean, if you want to have a name that no one else is going to have, you go, Karen. Right. If you want to be an individual. But, like, would you do that to your kid? Yeah, you probably wouldn't. So it's weird how names go extinct.
B
Like, names are hard.
A
Names are hard. Names are cyclical. You know, I'm watching the. The Golden Girls. I'm a big Golden Girls fan.
B
What is that?
A
What is the Golden Girls?
B
Is that a show?
A
Stop it. Don't do this. Don't ruin this episode. We're having one of the best podcasts ever made. I can't have you not know who the Golden Girls are. Sophia. Blanche, Rose.
B
I'm looking at it on the screen.
A
Thank you for being a friend. Yeah. The best theme song of all time.
B
Seven seasons. Wow.
A
Thank you for being a friend. Yeah. It was about three older women living together in my Four Older Women, But Rose was the grandma.
B
You're watching this.
A
It's the original Sex and the City. Truly. Truly. There was Rose, Blanche, Bea, Arthur. Give me the names.
B
Why are you watching this? Why?
A
Well, Betty White was in this. This was her show.
B
Why are you watching this?
A
It was a sitcom. I love watching it. Every night before I go to bed, a little bit of Golden Girls.
B
No, you're.
A
No, you don't. I swear they have. And it's crazy how relatable the show is. Like, they have issues about dating, getting older, their sons coming in the picture, their ex husbands. Sophia. She lived in Italy, too. Sicily.
B
I don't know anything about this.
A
Why did I bring up the Golden Girls? Oh, but all These names are coming back. I just wanted to tell you I like the Golden Girls. These names are coming back. Sophia. Blanche. I think there could be a Blanche. I think Blanche could make a comeback.
B
And that's a first name?
A
Yes.
B
Blanche.
A
Did you get dropped here on Earth five years ago? Golden Girls isn't like a deep cut. I didn't bring up perfect strangers. I didn't, like, look at you and go, you know, balky Bartonimos like that. I would say. I would go, okay, yeah. Not everyone knows remembers balky Bartanamos. You're looking at me like I'm speaking literally French. You are looking at me like I'm speaking Chinese. The Golden Girls. What did you watch growing up? What did you watch? Star Trek. Star Trek. Oh, we were on different planets.
B
Literally.
A
Yeah. Quite literally.
B
Yeah. And I never watched Disney. My family wouldn't let me watch Disney.
A
What part of Pennsylvania are you from? Like, no, I'm from Texas. You're from Texas?
B
Yeah.
A
From, like, Hill Country?
B
No, from this little town called seat. But I grew up Southern Baptist, and Southern Baptist boycotted Disney.
A
So. Yeah, The Golden Girls. Yeah. A show about three. Three women fucking in Miami in their 50s.
B
Probably not.
A
Probably not for the Southern Baptist community.
B
Yeah.
A
What did you guys watch?
B
Star Trek.
A
So Star Trek made more sense for Southern Baptists because it was like, this is fantasy. Like, there was no thought of, like, the science of it, I guess.
B
But when I was little, man, I could, like, recite the whole thing. I'm like, you know, I don't even remember what it is now, but it's like, in a galaxy far, far away.
A
Yeah, no, I. That I'm.
B
But I'm familiar with Star Wars. I don't even know, but whatever.
A
I'm not a Trekkie, but I'm familiar with, like, Captain Kirk and.
B
Yeah, I watched them all. Every. Every, like, different captain that came through Starship Voyager.
A
Picard.
B
Picard, yeah, all of them. Captain Kirk.
A
But no relation to the Golden Girls.
B
I never even watched.
A
I haven't go watch one episode.
B
I never even watched one episode of Seinfeld.
A
You've never watched Seinfeld?
B
No.
A
I must be like an alien to you, then. Well, you must meet Jews. And you're like, what is this? What is going on?
B
I don't know anything about.
A
What's with this loud, hairy man? You must be sitting here like, he's.
B
Well, the Golden Girl really threw me through a loop.
A
He's mad, but he talks like he's. He's mad, but he's not mad. You Must be like.
B
And you're watching Gold. Like, four old women.
A
Elder. Easy there. They're right. I think they're around your age on the show.
B
You.
A
Yeah, they're 38. Three elder. 38 year olds.
B
Yeah.
A
Hanging around Miami. The way they talk about sex in the show is wild because they are. They all look old. Like, they're made to look old. And they show this, like, Southern Florida home that they're living in. And it's like. But they're always talking about sex. It's like, crazy. It's so funny. If you like. If you kind of remove yourself from it. Like, Blanche is supposedly the Samantha, like, from Sex and the City. She's like the Samantha character. And she's like, ooh, I'll take him out back and I'll show em a thing or two. And you're like, I can't believe Blanche is talking about blowing a guy. She's 80. This is crazy.
B
I'll have to write this down so I don't forget.
A
If you forget watching the Golden Girls, I can't even understand that. Watch one episode. I would love to. Like, I wish there was a picture, like a video of your face watching it being like, what.
B
What is this? Okay.
A
It's 22 minutes.
B
Oh, that's it.
A
Classic.
B
That's all I could last.
A
Yeah. I guess I have something in common with the. With the Golden Girls. Well, Jared, it is always such a pleasure to come here and hash it up with you.
B
It's great. I'm glad you came back.
A
I'll be back for the next baby.
B
Okay?
A
What if I just come back? Every time.
B
Every time.
A
I'm like, okay, bring in Jared. No, this is a blast. I'm happy for you. I'm happy for the growing family and you and your 40 millionaire. It ain't 100 million, baby. Lot. Lot of it's in real estate. That ain't paper money.
B
A lot of it is in real estate.
A
Yeah. Hotels. That's good for them.
B
Whenever they get built. Come.
A
I'm in. Where are they gonna be?
B
One will be in San Antonio and one is in Houston. Those are the two being built right now, I think.
A
San Antonio. I gotta go back. It's been a long time on the rise. I always loved. I loved San Antonio.
B
I like San Antonio.
A
I was. It always felt like San Antonio was the. Like, I. I didn't know it was this close to Austin. It's like an hour and a half from here, right?
B
Yeah.
A
Yeah. San Antonio seemed to have, like, the right mindset because they Were around Austin and Austin was a little too confident. And San Antonio, like, knew we aren't that big a. Yeah. And that's what made them cool. I kind of think of Sacramento the same way.
B
But they're big now.
A
They're getting big. I mean, well, you got. The basketball team's good again. So I'm.
B
Are you. I'm rooting for the spurs. For sure.
A
I'm rooting for the spurs just because I like personalities. And it seems like when Banyama. I'm not even saying the name right. Probably.
B
I think you actually did say it. Yes.
A
He just seems like a fun personality. He seems like a good. He could end up being a villain and I would love it.
B
Yeah.
A
Like, I like when I like sports with storylines, and it feels like we get less of those every day.
B
I was watching the spurs the other night, and one of his teammates came out and was saying that women. Yama has this, like, crazy routine where, like, at night, after, like, 9 o', clock, he won't look at blue light and he, like, reads books and he's like, very, very deep and, like, philosophical, which is just. As a basketball player.
A
Well, he. If you think about it, he's a child star, you know, like, he didn't. We think of basketball players because. I think maybe because they're tall.
B
Yeah.
A
We don't think of their age. He's 22 years old. I know, 22. And you've been training for this since you've been, like, born. Right. Like an Olympian would. You know, I think in the Olympics, we think of it like, wow, they spent. They changed their whole life to be a swimmer. Like, wow, they barely went to high school. They had to get tutors. They had to. So did wembanyama. Like, this guy's life was dedicated to this moment right now. And it's like, yeah, I wouldn't. I. I guess I. I don't know if I could do it. Like, When I was 20, I went to college. I couldn't even. I didn't even know how to sign up for classes. Like, you know what I mean? Like, they'd be like, did you go to the bursar's office? I'm like, what's a bursar? I remember I was like a freshman in college. I didn't know anything. And then I am like, oh, God damn it. These athletes, they don't know what the fuck they're doing. It's like, Jared, you couldn'. Find the homework. Like, I couldn't even sign into the portal. I just started Going to the doctor.
B
Like, it's like, I do think that being an athlete would take. It takes superhuman to be, like an amazing athlete.
A
We don't have. It's. It's one of those things. It's like right in front of us and we see it on tv, so we don't really. If you think deeper on it, you're like, man, yeah. What's going on here? And they. Everyone's like, oh, they make so much money. Well, the whole country is watching one thing. Five guys, you know, like, yeah, they're the CEOs of that company. Yeah, it's five. You know, they're the board members.
B
So it's fun. I've enjoyed watching it. I usually don't get, like, really invested in watching games, but the playoffs have been fun.
A
They've been fun. I think basketball playoffs, if they could fix the regular season. I don't know how they do it, but basketball playoffs are fun to watch. And the Knicks are good. I mean, the Knicks are going to be in the finals, so.
B
Yeah. Okay. Well, I wish you all the best of luck.
A
Thank you.
B
Thank you for coming back on my show.
A
A pleasure.
B
Please come back soon.
A
Yeah.
B
I'm so happy you're happy.
A
Thank you. And I got the book. Did we talk about it? We can they pre order it?
B
Tell them. Tell them.
A
You tell them. You got to tell them out. By the time this comes out, it's out.
B
It's out now.
A
It's called Walking Red Flag. It's dating advice book. There's laughs every page. Jokes every page.
B
I love it.
A
Personal stories about dating. It takes you from getting dumped to getting dumped again because that's all I ever knew. So basically, you get dumped. What do I do? And I give you personal stories of what I've done and suggestions I would give if I could tell myself easier to give advice than to take advice. But the whole book is like, just. It's fun and it's meant to make you more positive about dating. If you're a guy and you want to feel seen and heard, the book will make you feel that way. It'll talk about the insecurities I have dating, and I think you'll connect with it. And if you're a woman, you want to get inside the mind of the man, it'll do that for you.
B
I love it.
A
Yeah.
B
Congratulations.
A
Thank you. Thank you.
B
Thank you. Thank you guys for watching another episode of First Date. We'll see you next time. First date. Baby, are you really drinking a girl glass of milk with dinner? First date. I can't wait. You told your mom about me? Just say you're ready. Delete my number. First date. Your parents are your roommates. First date.
C
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First Date with Lauren Compton | YMH Studios
June 9, 2026
In this candid and comedic episode, host Lauren Compton sits down with returning guest Jared Freid—comedian, podcaster, and now author of "Walking Red Flag: Dating Advice from Your Favorite Guy Friend." The two dive deep into the complexities of dating and relationships, reflecting on red flags, breakups, gendered dating norms, confidence, family, and finding love when you least expect it. Jared shares his personal journey from confusion and ending the "right" relationship to rekindling it years later, providing both humorous and heartfelt advice throughout. The conversation also touches on food culture, family stories, and playful tangents about pop culture, making it a lively, relatable listen for anyone navigating modern dating.
On Gendered Dating Pressure:
"Women go out with guys that they have no attraction to because a friend was like, 'He's great.' And then they go, 'I just don't know what's going on here.' And I'm like, you do know what's going on here. You have permission to be turned off." — Jared (02:47)
On Excitement in Relationships:
"I was all, you know, you question whether you can get excited. I'm like, I've never wanted to make a friend ever. And now I believe at 41, I'm gonna make a best friend." — Jared (18:11)
On Social Media and Breakups:
"That's called orbiting—when you don't want to be with someone, you're unsure, like, you're not together, but you have some level of interest..." — Lauren (15:14)
On Growing Up (and Food):
"I wish a woman would be as obsessed with my body as my parents are." — Jared (43:14)
On Pop Culture Gaps:
"Did you get dropped here on earth five years ago? Golden Girls isn't like a deep cut." — Jared (50:28)
| Timestamp (MM:SS) | Topic/Quote | |-------------------|--------------------------------------------------------| | 02:47 | "You're not confused, you're turned off." | | 04:24 | Breaking up before milestones/holidays | | 08:31–10:54 | Jared meets and breaks up with partner (first time) | | 15:14 | "Orbiting" and the impact of social media after breakup| | 17:22 | Getting back together and revealing she’s in his book | | 18:11 | "Relationships are a big frappuccino of delusion and logic..." | | 22:00 | Lessons learned from dating in your 40s | | 23:32 | Gaining confidence and quitting drinking | | 24:08 | Rants about food videos and online commenters | | 38:21 | Office wet wipes and corporate bathroom perks | | 41:20 | The joy of single nap schedules for parents | | 47:29 | The challenge of baby names and exes | | 49:00–53:12 | Lauren’s unfamiliarity with "Golden Girls"/Seinfeld | | 58:42, 59:23 | Jared’s book pitch: "Walking Red Flag" |
The tone is conversational, fast-paced, self-deprecating, and fun, with both Lauren and Jared riffing off each other's stories. Jared is unfiltered but relatable, weaving between vulnerability and his signature observational wit. Lauren balances humor and curiosity, both as a fellow storyteller and as an interviewer.
This episode offers an honest, laugh-out-loud look at dating, modern anxieties, and the path to finding (and keeping) love. Jared’s story about breaking up with "the right person," then working up the courage to reunite, delivers hope and humor for romantics and cynics alike. Along the way, the duo dish out plenty of hard-won advice and playful, memorable moments.
Jared Freid’s new book, "Walking Red Flag," is out now. For more, check out his tour dates at jaredfreid.com.