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The JTrain Podcast
Marriage, Prenups & Red Flags with Ashley Hesseltine - CHIT CHAT WEDNESDAY
00:45:08
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- [00:00]
Jared Freed
Chit Chat Wednesday for you to listen to. I have a guess who will be your new boo. You're gonna love them too. Chit Chat Wednesday. I hope you're having a good day today. I hope it's gonna be a perfect week too. I hope you have a nice poo. It's a Chit Chat Wednesday too. Hello and welcome to the J Train Podcast. This is Jay Train Jared Freed coming
- [00:40]
Ashley Hesseltine
to you live
- [00:42]
Jared Freed
from Delray Beach, Florida. That's right, every Wednesday is a Chit Chat Wednesday where I sit with a comedian, a friend, an expert. Today we are lucky to have all three. Comedian, friend and expert in getting married at 42 years old, everybody. The co host of the Girls Got to Eat podcast, Ashley Heseltine. Thank you for coming on the show.
- [01:12]
Ashley Hesseltine
What an intro. The 42 year old bride.
- [01:15]
Jared Freed
I listen, I, I thought that was very interesting part of the special which is what we're here to talk about. The special is wonderful, it's hilarious and everyone should go and watch it. It's on YouTube right now. It's waiting. The gift of 2026 is that it's waiting for you to watch and laugh. Here Comes the bride. That's what it's called. And, and you. It revol. You know, you have video from the wedding. It's great. It's wonderful. Congratulations. How do you feel?
- [01:41]
Ashley Hesseltine
Thank you. I feel great. I feel so proud. I mean this was a real journey. I, this material spans like two and a half, three years really from moving from New York to la, deciding I was wanting to find my partner was going to turn 40 that year. I was like, I want to get this done before I enter this decade of my life. And then dating in la, meeting my or connecting with my now husband and then all of the moving in together and the wedding planning and I toured it all in 2025, shot the special in October, three weeks to the day. I got married three weeks later. So it was chaotic. It was insane. I was like touring and planning a wedding and doing all the things and it, it turned out so well. I wanted to feel wedding ish. I wanted to incorporate the real moments from the wedding, the real footage. And I'm just so proud, I don't know, like I, I'm proud of you.
- [02:35]
Jared Freed
Not to say it doesn't sound demeaning. I mean genuinely, it, that's a lot to do and it, and it's great, it's hilarious and everyone's going to love it that you did a great job.
- [02:46]
Ashley Hesseltine
Yeah, it was funny because I was, I really Love the name. My tour was called Sex Before Marriage. I was like, I don't want to put sex in the title. I did. Not that I. Because nothing against what I think, but just, you know, may as well not set that roadblock up for myself. And then I had this idea to call it 42 year old bride and I was like, it's just a little close to 37 and single. Oh really?
- [03:08]
Jared Freed
Listen, I know 42 well. I was thinking about the plight of a 42 year old woman getting married. I think it's like kind of like don't think that's what it is. What's that?
- [03:23]
Ashley Hesseltine
You pay for your own wedding.
- [03:24]
Jared Freed
That's what will you pay. Right. Do you. What what made the change? Do you think making money in and having your career set is what made your mom. You know, you say in the special, you say that I was never the get married girl, you know, and do you think it is career set? You know, having a career is what made you want to get married. What, what made the change.
- [03:47]
Ashley Hesseltine
I always wanted to get married when I was younger. I've never wanted kids. That was never a thing I was interested in. I talk about that in the special as well. Yeah, and I did want to get married. Jared, when we first started the podcast in 2018, I said on the first episode, February 2018, this is the year I'm getting engaged. Like LOL. So I really did want to. And then as time, yes, it was like career. I was making my own money. I mean again, this is all in the special. And it's true that I was like, I don't know the need for this. And even getting married as we were going through the process and we did a prenup, which is the whole thing and it's stressful and invasive and I was like, what is the point of this? Like, I'm not changing my last name. We're not having kids. We're not combining all of our assets really. I mean some, but we're keeping a lot separate. So traditionally those are the reasons to get married. I mean the love and the commitment and everything. But it was still on my mind and we had, we had these conversations, but I'm really glad we did. It was important to him and both of our parents are still married after 30, 40 years. And it's important to us and I'm glad that we did it. But even to the.
- [04:58]
Jared Freed
The week still have like why we need to do this.
- [05:02]
Ashley Hesseltine
I mean, not in a. I tread lightly there because I would hate for his. Him to get his feelings hurt in any way. But he knows that even up to it, especially during the prenup. I'm like, I. I asked him, like, we don't have to do that. We could just have the party. Do you really want to do the thing? And he was like, it means a lot to me. And I'm like, no, you're right. We should do. We should do it.
- [05:23]
Jared Freed
Well, I was there the first night you guys went out.
- [05:27]
Ashley Hesseltine
That's crazy. So I feel part of that night in Boston. You're totally part of the story.
- [05:33]
Jared Freed
A part of it. And he. I remember, you know, because I thought when I'm watching the special and everyone go watch it, the link is in the bio, this episode, wherever you're listening or watching. And, you know, I was thinking about all that stuff because you. You. Well, you say the reason to get married is that. And it seems like. And I think a lot of women probably related this idea of, like, a guy sneaking up and ending it and, like, putting barriers to that.
- [05:59]
Ashley Hesseltine
You can't just leave. You.
- [06:01]
Jared Freed
Right? There's a whole process. You. It's not even like, if you're living together. It's way harder than that, right?
- [06:07]
Ashley Hesseltine
Yeah. I mean, lock them in with a home, a kids, or a marriage. I mean, one of those three things. It's going to make it harder to just up and go. To just go.
- [06:19]
Jared Freed
There's little trust for a man rethinking what he's doing when he's, like, ending something. Because maybe. I'm sure women have dated me, and they're like, did he even think about this? Like, did he even think of this? And I'm like, you know, I. I guess that could. The accusation could be true where it's like, I don't know if I'm thinking about that going in, you know, Like, I'm not thinking. I'm like, she's hot. I want to, you know, go out with her. Like, you know, it's like, very simple. Like, the box checks aren't as thorough from my end. And maybe that's why on the way out, it's not as thorough to be like, yeah, but we've built something. You know what I mean? Like, I don't know.
- [06:56]
Ashley Hesseltine
I mean, you hope that it doesn't come to that. You hope that your. Your spouse is not trying to leave and ghost. And they're like, I gotta stay around to do the paperwork. I mean, you would hope so. I. What is Azul?
- [07:12]
Jared Freed
Is the dog okay?
- [07:13]
Ashley Hesseltine
He's just. It's a. You can hear it. He's like just whiny. Let me just open the door.
- [07:17]
Jared Freed
He seems sad. We are sponsored by Quince. I wore a Quince shirt last night. It was a short sleeve polo that was knit. I loved it. It looked great. I, I can even send the a picture to flash up here. I have a picture of me before I went and did my show in Vegas. I love the shirt. It, I would say great gift for any guy in your life. They'll love it. They'll feel comfortable in it. I wore the xl. It's it, it has moved. I got it a couple weeks ago or a couple week, a couple days ago. And it's now a front of the rotation shirt for me. I after one wear I, I, I'll send the picture. I'll post it right here. It'll be right next to me on YouTube. But it's kind of what Quince does. High quality, versatile and built to last. European linen shirts and shorts that are perfect for summer. Protech golf pants and polos for all day. It's just there's no logo. It's, it's subtle and it looks nice. It could be worn up or down, you know, meaning like it could be casual. It could be a night out. I wore mine on stage. I really love the shirt. They have belts, briefcases and shoes so. And they cut out the, they, they cut out the middleman. That's what they did. There's no store to go into for Quince. So it's going. The savings are being passed on to you. They partnered directly with ethical factories and top artisans. No middleman means you spend 50 to 60 than similar brands. So anything that you're being served as an ad right now that you're kind of thinking about, Quint is going to have that same outfit for less probably. So I would go to their website and I would just check it out. Refresh your everyday with luxury you'll actually use. Go to quint.com jtrain for free shipping and 365 day returns. Now available in Canada too. Go to Q U I n c e.com j train for for free shipping and 365 day returns. Quints.com j train a dog.
- [09:25]
Ashley Hesseltine
That's another way to keep you locked in with somebody. No, I mean I my joke was always I think marriage should be 10 year leases. I think you should reassess after 10 years because people obviously stay locked in longer than they should. But yes, my joke in the special is like this is how to make sure no one just up and up and leaves. You get the government involved, you sign paperwork about it and then if they ever try to leave, you have to hire legal counsel, you know, so. But you know that people just leave 10 year relationships or.
- [09:57]
Jared Freed
I know. And the joke works because the fear is there. This I. And I think it's like, you know, when you hear about like she just up and left from like went from a guy. You. You go, well, what, what, what, what did you do, sir? Like you kind of have that first thing with a guy who's like, my wife just left. You're like, well, how bad of a husband were you? It's kind of like my first reaction, which isn't fair.
- [10:20]
Ashley Hesseltine
I love that that's, you know.
- [10:21]
Jared Freed
But like I think a lot of people are like that. And when. When a woman says, well, he just like ended it and they're like kind of like shell shocked. How did that happen? A lot of people are like, yeah, that's happened. I hear about that all. You know, he must have just been afraid of commitment. You know, like it does you.
- [10:39]
Ashley Hesseltine
Do you know this book, Strangers. Have you heard of it?
- [10:41]
Jared Freed
No. What's that?
- [10:42]
Ashley Hesseltine
I mean it's. I guess it's. All the girlies are reading it, but this is this book, this woman's real life story of her husband of 20 years, three children, multiple houses, wealthy family in New York City. I mean they had some skeletons in their closet, but just totally up and leaving like first week of quarantine and was just like, I'm out. He ha. He was having an affair. But she was like, we could work through that. And then he was like, no, this is over. And it was just super cold the whole time. And that's why the book is called Strangers. She was like, who did? How did I not. I didn't. I don't know this person. So you can, you can do it. I think that. But you still. They're still. They had years of getting a divorce. So I think that's what it is. Like, we're joking about it. But I do think if you want to up and leave a marriage, you are more inclined to go to go to counseling to talk it through. Like, you can't just walk out the door.
- [11:35]
Jared Freed
So the first you guys went out, the first night you guys went. Right? The first guy night you went out, I remember it vividly. You had a show in Boston. I came as the special surprise guest and he was. The whole premise was that he had come to your show before with his then girlfriend and then he like, you guys DM'd when he was at that show. Right.
- [12:02]
Ashley Hesseltine
He came to the show in 2021 in Boston. We did the Wilbur, and his best girlfriend had written in that. We're coming with our friend Shashank. And he has a crush on Ashley. He had seen me on a, like, Covid virtual show we did for the 2020 holiday show and was just, like, enamored with me, which is crazy. I had my original face, you know, which I mentioned that in this special as well. I was like, if he liked me then, I mean, just wait and see me now.
- [12:35]
Jared Freed
So model.
- [12:36]
Ashley Hesseltine
Exactly. So, yeah. So you have this, like, I hate to even use the word celeb, but he, like a hall pass type crush on me. So they came to the show in 2021.
- [12:46]
Jared Freed
That's why. Well, that's why that whole hall pass thing, anytime it's said to me, I don't trust that couple at all. There's not. There's something wrong. And it gets said to you. You know this. It gets said to you in a way, like, oh, he's he. You're his hall passer. Like, oh, she's always talking about you. And you're like, I, I, I, like this joke isn't fun for me. I think there's something off about the marriage. Like, you know what I mean?
- [13:12]
Ashley Hesseltine
I'm not famous enough to be your hall pass. Like, this is right.
- [13:15]
Jared Freed
There's got to be a number. Right? Right, right. That is that it has to be unattainable for the spouse. Because I'm like, whenever it said to me, I'm like, well, I'm here. We can go in the bathroom right now. Like, if you want to, like, get this over with, we'll scratch it off the list. Like, right?
- [13:33]
Ashley Hesseltine
I mean, like, I it. And like, if you're a performer, what size venues are you doing? We're at the Wilbur. Like, I'm not at Gillette Stadium. Like.
- [13:40]
Jared Freed
Right, right.
- [13:41]
Ashley Hesseltine
You're in. They're in row B, you know, so I can.
- [13:45]
Jared Freed
It's a little too real. It's like, well, it's like when women are like, you know, a lot of times we'll have people write into you up. They'll be like, I'm. I'm in favor of, you know, sex work, and I want people to get paid for what they do. And then they go, and my boyfriend's following an only fans, and they have 1500 followers on Instagram. And I feel weird about it. I'm like, yeah, that's fucking weird. I understand that.
- [14:06]
Ashley Hesseltine
Wait, Jared, do you watch hacks?
- [14:09]
Jared Freed
No.
- [14:10]
Ashley Hesseltine
Oh, so in hacks, watching everything. I'm obsessive tv. Yeah.
- [14:14]
Jared Freed
Yeah.
- [14:14]
Ashley Hesseltine
I make time for it. It's really important to me. In the latest episode we watched last night, Hannah Einbender's character is dating a sex worker in Vegas. And she's so okay with it, and she's, like, loving his work. She talks about who he's fucking and whatever, and then she also finds out he's a magician, and she's like, that's where I draw the line. It's this very funny thing of, like, state can date a sex worker, but not a magician. Okay. So he. They come to the show and we read the email and it's like, we're doing it a light way. I mean, people come to the shows with their husband and they're like, my husband has a crush on Raina. Like, let's have an orgy. You know, like, it's light and fun, but we crowd worked them a little bit. I'm not going to get into the details. It didn't go well. He. He is just kind of a serious. He was just more serious. He wasn't really prepared, I don't think. Like, I think his best girlfriend was like, this is the chance, like, we're going to be in the room with Ashley. You have a thing for Ashley. You know, I'm going to write the email, I'm going to send it in. And that was a part of, like our. She was part of our wedding and everything. And his girlfriend was not this long term, years long was an off and on thing. They, you know, under a year, back and forth, off and on, whatever. Just to clarify. And you know, the crowd work stuff didn't go that great. Like, I was like, that guy kind of seems like an asshole. Even the way he was. He wasn't just. He wasn't really in on it and neither was she. And that was kind of it.
- [15:38]
Jared Freed
Looking back, you can understand.
- [15:40]
Ashley Hesseltine
Yeah, like, literally, like, he married. He married me. So he ends up in my DMs, like, months later, you know, they'd broken up and just here and there, messaging back and forth. If he saw an opportunity to weigh in on something. I was posting, always flirting ever too over the top, but very much still had a crush on me. And when we went back to tour in 2023, again, this is really true. And this is what I talk about in the special. I was on a mission to find somebody. I was like, I. This is the year I'm not turning 40. Single. I just had this terror about it. And we were on the road meeting guys and whatnot and we went back to Boston. If certainly I wasn't thinking that was my husband, But I just DM'd him thinking, like, I wonder if that hot tall guy is still into me and if he's single. So I just message him, you know, our last message was weeks prior, a month or two prior, whatever. And I just was like, are you coming to the show? Are you still traumatized from the last one? And he was like, I'm not going. But the same girlfriends were going to the friends. And he was like, can I finally take you out? And you know, I'm like, take me out, I'm working. You can come to the theater after. And that's what happened. I mean, he showed up at 11pm we're all in the green room. We had like 20 people in the green room. Intimidating. We'd all just been doing our thing. And he showed up like, I mean his friends were there at the show, but he showed up solo. Our assistant went and got him and brought him down and we hit it off and he stayed in the hotel with me that first night and we were together ever since.
- [17:14]
Jared Freed
I remember that night because I kept thinking about it. In the beginning of your special, you're talking about dating and how, you know, getting a task rabbit and you know, and dating a guy. You know in L. A you date a task rat you if you want to fog because he's good looking and an actor and good with his hands. All these are great jokes and great ideas and it's, I was thinking about, you know, you were talking about like things that like made you turned off to men, things that gave you the ick in the special. And you're talking about things that you didn't like and the women are on board. And I was thinking of that night with your now husband and how he played it so correctly. And it kind of goes back to the crowd work, not working. Like, he's a reserved guy. Yeah, he, and I like him. I've anytime I've hung out with him. He's a good guy. Like, I'm like, I, I, I understand everything. Like awesome guy, Boston guy. But he was like, he was like a good, like he wasn't there to be the show. He wasn't there to like, hey, I'm the one going on a date with her. Like, it wasn't. He fit in. He, he was, he was. And I, I was thinking, I was like, is it. And I want to ask you this. Is it a bad thing for a man to be an extrovert?
- [18:31]
Ashley Hesseltine
Well, let me ask you first. Or do you. Do you identify as an extrovert?
- [18:37]
Jared Freed
No, I wouldn't identify myself as an extrovert at all. Like, I. I think he. Okay, I was just. Remember that night, watching him. Like, I would never go say I'm chilly. You know, like, oh, oh, Burr, I'm cold. Like, I would. I wouldn't be a performative guy. And I think that's, like, when you hear a lot of the female icks, it's like, it's just an extrovert. It's just a guy who's like. Walks in a room, is like, hey, everybody. And you're like, don't do that. You know, because he. I mean, he was subtle.
- [19:06]
Ashley Hesseltine
Oh, my gosh. Totally. No, it's hot. He's really, like. He couldn't be farther from that. He started this app. It's incredible, by the way. It's called Kitchen Sink. And he. I'm giving it a plug. But I'm also telling you, we've had to shoot some. We had to shoot some content Jared. And so I'm helping him, and he hates it. And I love that about him. Like, the first time we did his, like, founder video, he was like, I hate. He wouldn't do it. Like, third take, he was like, we're done. You got to figure it out in post. Like, he. He. We have no risk for him to become an influencer. And I love that. And what. You know, I want to tread lightly because obviously, I certainly even have friends, guys that I love that are. That create content. You know, they do.
- [19:50]
Jared Freed
You're not fucking them. That's.
- [19:52]
Ashley Hesseltine
But I would never. That's the point. For me. For me, personally, I don't want a guy that has a public Instagram, if I'm being honest.
- [20:00]
Jared Freed
I've heard that before from people. And now I'm like, what's the truth behind it? I think that I was like, maybe it's just extroverts because, like, the, like, introvert male is hot. Like. Like. Like it. You know, the. The crowd work not working on him. Like, I get. I could see how it just wouldn't go the right way with him. I wasn't there for that night, but I'm like, he'd probably, like, what the. No, I'm like, I. And I.
- [20:26]
Ashley Hesseltine
It was bad.
- [20:26]
Jared Freed
Yeah, right? But then the guy who's, like, into it, and, like, you know, you'd be like, get out of here. Like, you know, I don't know if
- [20:36]
Ashley Hesseltine
they're not actually funny or something. I mean, there's. There's like a quiet confidence about him. That's a trait that this, like, kind of mystery. He's ob. He's tall, dark and handsome. Just, you know, literally. And so it. That is here. I think I was wrong about what I wanted in a man. I. And I talk about this. I don't think I mentioned this. I mentioned that he's from Boston especially, but I don't think I really talk about this. But I always thought I would want a guy from New York or la, because that's who I am. Like, I've only really. Those are the two cities I choose to live in for what I do. I was like, I just. I was so wrong when I thought I would only vibe with somebody in one of these cities because they would match my personality and who I am and the things that I value in life and the lifestyle that I want to live. And I couldn't have been more wrong. We joke that it is a red flag for a man to want to live in la unless you really have to for work. But why are you living here? Why are you coming here? And I don't think, but.
- [21:38]
Jared Freed
But even if you're a lawyer in la, you're like, you can live like, the best lifestyle being a lawyer somewhere else. Like, I. I have friends who live in LA as, like, real estate. And I'm like, I kind of get that more. Like, yeah, I don't know. I. I meet lawyers, like, in Pittsburgh, and I'm like, you did it. You did the smart thing. You can be a lawyer and you can run Pittsburgh. And you're like, you know, like, I kind of like, you can live In a castle 20 minutes away, you know, whatever. You go to work for a few hours and then, I don't know, there's more. You're getting more out of life.
- [22:11]
Ashley Hesseltine
Yeah. So to answer your question, I think it's. It's interesting just to reduce it to extrovert, but that really could be it,
- [22:21]
Jared Freed
you know, And I think maybe the dog's an extrovert. That's why he's crying.
- [22:24]
Ashley Hesseltine
He's like, he couldn't be more introverted, but we don't want, like, that's. The people take away from this. They're like, Ashley, she neglected her. Her dog, the whole, the whole podcast.
- [22:37]
Jared Freed
The dog doesn't get fed.
- [22:39]
Ashley Hesseltine
I think that I. It's interesting when I see two people in a couple that are both like, content creators. You know, like, they're both. We, we know a couple that has since broken up, but they both really liked the spotlight, and I don't see how that works. I don't know how you feel about that. That doesn't work, in my opinion. I think, obviously, actors and people in entertainment date each other, but two people who genuinely want the spotlight, how does that. I don't think it works. I think you're fighting for the spotlight.
- [23:19]
Jared Freed
Right. It's tough. I, I, you know, I guess you got to cheer for each other, and if you feel that you're somehow competing, it's tough to cheer. And. I don't know. I, I. You're talking about making content for his app. Like, you're cheering for him and in helping, like, that's a, That's a. Oh, yeah. That's a show of, like, let's go. I'm in. Let's. We're doing this. You know, when you do something. We do.
- [23:43]
Ashley Hesseltine
Oh, yeah.
- [23:43]
Jared Freed
I, I have a question. So you mentioned something in the, in the special that I wanted elaboration on. You were in DUI school. What happened that you got a dui? How did that dui. Like, that's a tough one.
- [23:57]
Ashley Hesseltine
Jared, is this serious? You don't know this store. You don't.
- [23:59]
Jared Freed
I didn't. Should I know this?
- [24:01]
Ashley Hesseltine
I don't know. I used to talk about a lot more and. Okay, I, My tone has changed.
- [24:05]
Jared Freed
I, I'm sure you're not proud of it. I. You can't be.
- [24:08]
Ashley Hesseltine
I'm not.
- [24:08]
Jared Freed
No. Yeah.
- [24:09]
Ashley Hesseltine
No, but I used to joke more like when we first started the podcast and people didn't like it. I was too flippant. I'm like, no, I'm not proud of it. You shouldn't drink and drive.
- [24:18]
Jared Freed
But people, you know, like, you, you, if you give any, like, people, I mean, look at the Tiger woods thing.
- [24:25]
Ashley Hesseltine
People are just like, yeah, it's, it's. And I'm a different person. I've. I've grown up myself. But, yeah, I had, you know, a couple when I was in my early 20s.
- [24:37]
Jared Freed
Well, you talk about, like, you talk about, like, there's other stories in the special where you're like, I got a couple in me, and I was that, you know, drove past my dad's place. But I'm like, the DUI school, like, you know, like, yeah.
- [24:49]
Ashley Hesseltine
So I.
- [24:50]
Jared Freed
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- [26:41]
Ashley Hesseltine
I did get a, I got a DUI as soon as I moved to Atlanta. Like I just, I drank and drove and it was a different time. Clearly we're talking, I mean I got my, I turned 16 and 99, you know, so these are not excuses. It's just, it was a different time.
- [26:58]
Jared Freed
No one really, I'm not even asking because I'm like mad about it. I'm just like, yeah. So I think it DUI is like a life changer to me. Like that is like a I gotta figure out moment. Was that.
- [27:11]
Ashley Hesseltine
Yeah, I mean I got one when I was like 22, 21. Like right. I, I've been drinking and driving all through college, high school even. And then the second I moved to a real city at Atlanta, there's a DUI task force. Like I mean two months living there I got a dui. You know, I was just living the same way and, like, you know, got in trouble, so. And then I got an. Another one five years later. So I was actually 27. I said, you know, I make a joke in the. The specialist. 28. But I was. I was 27. I mean, I was not. It was. There was no excuse. You know, it was like the. A weird night. I, like, was just drinking at a friend's house. You know, you're like, I'm in sweatpants. I don't. There was no Uber. Like, I'm like, I can drive home. And I just. I think a lot of people have been there, and obviously I made it a terrible choice. And we have so many more options today. Like, I always say, if we would have had Uber, I think I would have got one. I don't think I would have got multiple. So I did date a guy that I met on my DUI journey.
- [28:20]
Jared Freed
Right. Well, listen, I remember, you know, there's moments I. I remember there's like a next morning moment where you're like, things got to change, and then you don't change. And then, you know, then the next time you go, okay, now we change. I. I remember I was walking home. I, like, was hammered. I slept at this girl's place in the Jersey shore. Woke up the next morning, like, took off my shirt, was walking home shirtless in jeans, and I'm 22, and I'm like, what am I doing in my life? And then suddenly, a black Lincoln Navigator pulls up besides me, windows go down, and it's my roommate from freshman year of college. And he's like, jared, are you. And you were shirtless and jeans, shirtless and jeans. Like, the worst look, the worst morning look. Like, the most not morning look. Smelling like booze, hair everywhere.
- [29:13]
Ashley Hesseltine
Yeah.
- [29:14]
Jared Freed
He's like, jared, how you been, man? He's doing great. He's like, yeah. He's like, I work at the museum now. And I'm like, ah, yeah, I got no card. I'm walking home, you know, Like, I haven't even brushed my teeth. Like, do you need a ride? I was like, that's like the last thing I want on earth is a ride from you. Like, and I just, like, 22. I feel like one of the. Is that age where you're like, I should be grown up. I've been told. And then something like that happens. It, like, hangs with you. I don't know. You mentioned 22. Made me think.
- [29:48]
Ashley Hesseltine
Yeah, just. I don't know. I was just such. I Was just a brat. I was just irresponsible. I was just privileged and just. I don't know. You just think nothing. You think you're invincible. All the things you know. But how I am now is like. And since I got that second one. Is it because. Almost an overcorrection. I have a real zero tolerance. Drinking and driving. Like, because you can have. You can drink and drive a little bit, you know, it's not illegal. You can have a drink or two and drive. Most people do, you know, And I am really. I, like, with Shashong and with my friends, like, I'm. I'm that person. I've been that person for a long time. Because it's the thought of it happening again. Oh, for sure.
- [30:32]
Jared Freed
Ingrained. I mean, like, there's, like, kids that don't even want to get their licenses, like, that are, like, living amongst us. Like. Like, that's even a thought. Like, Uber is like, a thought of, like, that's how I'll do my life. Which I'm like, not a bad idea, you know? Like, I'm like, okay, you know? All right, well, part of that story is that your dad, you know, whispers to you that he basically does the most cartoonish bro joke that any bro has ever done. Coughing slut. At you. Going slut. Like, he's a bad guy from an 80s movie. And that made me think of this. Is it bad? Is that there's got to be a weird thing of, like, because your dad sounds like the biggest bro in the history of bros.
- [31:21]
Ashley Hesseltine
Okay, go ahead. Keep going. Keep going.
- [31:22]
Jared Freed
If he coughs slut at his daughter. It is a different dad than I have come in contact with by. But I.
- [31:30]
Ashley Hesseltine
Well, did you finish the special? Did you watch the very.
- [31:33]
Jared Freed
And I even think that. Yeah, I even think that that's the joke that he does on you, is a bro thing. Like a bro.
- [31:41]
Ashley Hesseltine
I've never thought of him like that.
- [31:43]
Jared Freed
He's to fuck with his daughter about her fucking a guy. Like, even bringing that up twice, bringing it up once is like, the most uncomfortable, comfortable thing. The. The second time, like, I would think that there's a weird space of, like, I need to find a guy that likes my dad but understands that is no, nothing like my dad.
- [32:06]
Ashley Hesseltine
That's interesting. The takeaway from my dad that you got by just the special. Because he's. I don't know. Everyone's obsessed with it. I mean, kind of the way they're obsessed.
- [32:18]
Jared Freed
I'm not saying, like, but he sounds like a guy I'd want To be friends with. But I would think it's like, he's.
- [32:23]
Ashley Hesseltine
He's like, when you. When you hear bro, dad, I'm picturing Southern Republican, like, maga dad. Like, he's this liberal guy. He's a pilot. Like, he's just has to make the joke. It's almost to a fault. Like, I think he should have been a comedian. Like, he talked to. He talked about doing stand up for a minute, like, at this open mic in Dover. Dover, Delaware. Like, he has to do the joke. Like, it's. You feel it coming in a social setting.
- [32:52]
Jared Freed
The political thing doesn't really. Like, I don't go straight there. I just hear dad who called his daughter, like, the cough joke. The. Like. Like, we all know that's a joke that's been done. Like, going. Going up to the slot slot. Like. Like, that's like the bully from a movie. Like, so I think that's a certain type of guy, no matter what their politics are, that, like, you introduce your boyfriend, like, and you're like, I want this boyfriend to get that my dad's a character, but I don't want him to be, like, the same character as my dad would. Would me and my. That's what. That's where my brain went.
- [33:29]
Ashley Hesseltine
I'm gonna answer Jared, but let me just clarify that my dad coughed sluts at me and my best friend when we were 19, and we walked into his work at 8am in our clothes from the night before, like, covered in booze. Like, he deserved it. Yeah.
- [33:43]
Jared Freed
You could go with lush. You could go with alcoholic. Like, there's other things. There's other punchlines.
- [33:49]
Ashley Hesseltine
Okay, you're right. You're right.
- [33:51]
Jared Freed
Listen, this is. This is what I took away. I. You know, I love the special. They. I thought it was a.
- [33:56]
Ashley Hesseltine
It's the best part of it. Like, you know, great. That's. It's. There's a story I tell my dad at the end. It's long. It's like. It's like, at the final blast, 10 minutes. And it's a hundred percent true. Like, my dad will come to shows, and people go crazy for it. People go crazy for Lee Hustle Time. They're taking selfies. Like, he's become such an icon. But when he came to this tour in 2025, they came to D.C. and they came to New York for the taping. Obviously, he's part of the special taping. People are like, oh, my God, is that true? And my mom just. It's true. You know, she gets. She has to weigh in and they like, eat up the attention. People don't like, believe that every word of it is, is true. But my husband is. He has similarities to my dad in, in some of their interests. They're just both car guys. I mean, through and through. They could sit and talk about cars forever. I loved it. Like, they have so many similarities in that way. Like, Shashank works in automotive. My dad worked in cars his whole life. They have a lot of like their first day meeting, they were out on my parents farm, like walking around the cars, the whole thing. So. But they are different. And my dad, really, he's like this dirty joke connoisseur. Like, he's a person. Like he's gonna make it weird at a family function if he's gotta drop the joke, you know. So I don't think my husband's like that. But yeah, that's. That's a funny thing to call.
- [35:25]
Jared Freed
Right. Would you date someone who had to make the joke? That. I guess that's the extrovert, introvert thing again, like.
- [35:30]
Ashley Hesseltine
But I don't. I just. He's not. He's still really cool. He's still like more up.
- [35:36]
Jared Freed
I'm not saying it's not cool. I like, I, I like both of those types. Like, I grew up, you know, I'm thinking, yeah, like, that's very Boston to me. Like, the Boston to me is like, Boston is this weird place where you are around the smartest people in the world and the biggest, like, in the world. And it's like. And I don't think that those groups interact as much in other places as they do Boston. Because, because Harvard, mit, you know, all the, you know, amazing schools, all the doctors move to Boston. Like, it's a big doctor hub. And then you have like, you know, your buddy from Southie who's a total piece of shit and has a very. Has a perception and is smart and knows where to make the joke. Like, that person exists there. Like, that's why, like, there's a lot of charm from people from Boston. But I. So I understand that like, your husband probably gets along swimmingly with your dad and I. But I, I'm wondering if, you know, that was where I was. Like, I was like, I wonder if, like, if you met a guy who was like, oh, you know, like, you'd be like, get away from me.
- [36:45]
Ashley Hesseltine
But when you, when you do it like that, it's such an ick. But I'm like, my dad did do that. Like, was I like, he really. I don't know. He's he pulls it off.
- [36:56]
Jared Freed
That's it. Well, that's called charm. Okay, we have one game I want to play before we go.
- [37:00]
Ashley Hesseltine
Okay.
- [37:01]
Jared Freed
You mentioned in the special that richer or poor is kind of offensive to you. That asking on the greatest day of your life, will you take them when they're poor is, like, offensive. And you can't even.
- [37:15]
Ashley Hesseltine
Well, just don't bring it up. Why are we talking about it?
- [37:18]
Jared Freed
Well, I'm going to bring it up. This is called Richard. This is called richer or poor. And your husband has this thing happen. How do you handle it? What's your move? Ready?
- [37:33]
Ashley Hesseltine
Jared, what the fuck? Okay. All right, fine. It's fine. I'm ready.
- [37:37]
Jared Freed
You ready? Your husband loses his job and says he wants to concentrate on his passion for deejaying.
- [37:50]
Ashley Hesseltine
I can. I can deal with DJing. Stand up. We're divorcing. You can't. That's not a.
- [37:55]
Jared Freed
So stand up would be offensive. That's why I didn't. So DJing, you're supporting it. You're okay with it. Whatever happens, happens.
- [38:03]
Ashley Hesseltine
You have to. You have to work in a. You have to get another. You have to make some money while you're not just quitting and not bringing any. Any money. If you're like, I'm going to quit my job, my day job, and work on my dj, and I'm going to be like, are you also going to work in a restaurant? You can't just stop working. And then.
- [38:20]
Jared Freed
What's the plan here?
- [38:22]
Ashley Hesseltine
What's. Yes, you have to make some money.
- [38:25]
Jared Freed
Your husband, like, if he.
- [38:27]
Ashley Hesseltine
If he lost his job, I'd support him. You know what I'm. You can't just quit and be like, this is on you now.
- [38:32]
Jared Freed
So I'm going to drive Uber to make kind of the money that I need.
- [38:38]
Ashley Hesseltine
Okay, fine. I have to support it.
- [38:41]
Jared Freed
Half.
- [38:42]
Ashley Hesseltine
I just. I have to try because of the paper.
- [38:45]
Jared Freed
How long do you.
- [38:46]
Ashley Hesseltine
Not just gonna leave.
- [38:50]
Jared Freed
How long does he have to be? Diplo, how long?
- [38:53]
Ashley Hesseltine
Six months.
- [38:54]
Jared Freed
Six months to see a. You got to see a check in six months.
- [38:58]
Ashley Hesseltine
Six months to Ibiza. If you're not there with a residency.
- [39:02]
Jared Freed
Yeah, that's the next special title. Okay. He wins. He wins the lottery. $100 million and says we change nothing. It goes into an account that we give to our kids.
- [39:18]
Ashley Hesseltine
Well, this is a trick question, because we're not having kids, but we change nothing. And we're.
- [39:22]
Jared Freed
We give to a charity. We change nothing. We give it to a charity.
- [39:25]
Ashley Hesseltine
Divorce.
- [39:26]
Jared Freed
Divorce. Why?
- [39:29]
Ashley Hesseltine
Well, you can give some to charity.
- [39:31]
Jared Freed
Okay,
- [39:35]
Ashley Hesseltine
okay. Yeah, like, who did I marry?
- [39:39]
Jared Freed
Right? Okay. He only tips 10% and.
- [39:43]
Ashley Hesseltine
No, no, no, no.
- [39:44]
Jared Freed
It's the right amount for a job well done and likes to tell people about it. How do you handle.
- [39:48]
Ashley Hesseltine
No, but it's like that we never would have got past date one, you know, so if he did that now I'm like, what lobotomy did you get? You know, but that's hard.
- [39:58]
Jared Freed
Basically, he watches a documentary and it convinces him that 10% is the right.
- [40:02]
Ashley Hesseltine
But then that's. He's a weird. Like that. What is? That's. Then he's this weird, susceptible to the Internet weirdo, like conspiracy theorist. Like, that's another.
- [40:11]
Jared Freed
We've seen people in our world get, you know, susceptible to it before it happens.
- [40:18]
Ashley Hesseltine
We're not tipping 10%. Like, that's. We're fighting in rest. We're fighting in restaurants.
- [40:22]
Jared Freed
You're having a full out fight. Okay, that's fine. Okay. He just. He wears the same thing every day. Has three versions of the same outfit to keep trading off. And he has one suit and one swimsuit to cover the other things in his life, as he says. Are you okay with this?
- [40:47]
Ashley Hesseltine
This is like Steve Jobs kind of thing. Yeah.
- [40:50]
Jared Freed
He moves towards a uniform life.
- [40:53]
Ashley Hesseltine
I can, I can deal with this.
- [40:57]
Jared Freed
I was trying to think of what events he would miss out on. Like, if he's wearing T shirt and jeans and that's the Nor, like black T shirt, blue jeans, nice sneakers, and then has one suit and a bathing suit, like, would it work?
- [41:13]
Ashley Hesseltine
But like. And then, then I. Then we have to do something. And he's like, well, it's one of these things, right?
- [41:20]
Jared Freed
That's it.
- [41:24]
Ashley Hesseltine
All this stuff is bad and all that.
- [41:27]
Jared Freed
Yeah. Listen, this is what I wanted to see how you respond and what you're.
- [41:33]
Ashley Hesseltine
You're about to be.
- [41:34]
Jared Freed
How do you handle the marriage? You said important, richer or poor.
- [41:38]
Ashley Hesseltine
But these. Well, we didn't say that. These things are very. The person has like gotten a head injury. They've changed into a different person.
- [41:49]
Jared Freed
You wouldn't get this far with them.
- [41:52]
Ashley Hesseltine
Right? Yeah. Like, this is not who he is. But that one is the least offensive. But here's the thing. All these, the clothing stuff, all these things are traits I would never date. Like this rigidity or this weirdness around, like, you know what I mean? But. So if he turned into that kind of person, I'd be like, what happened here? But we're diving too deep into the.
- [42:11]
Jared Freed
Would you date someone? What? What? What? Would you date a man who made like A who was like really the best guy you've ever met but was like an Uber driver and this is, and he didn't care about money and you know, going to the next thing.
- [42:27]
Ashley Hesseltine
So I make more, I mean I've, you know, we, this something I'm where I'm open about. I have a different type of life. You know, what, what I do. Like he has a normal job, he makes a normal good salary and he goes to work every day and now he's got his app and things like that. And so this, the sky's the limit for that. But I, he's a normal guy, you know, and I am not. You know, what we do is just, it's different.
- [42:57]
Jared Freed
So very normal. I make a lot of money too.
- [43:00]
Ashley Hesseltine
You know, I, I mean, I guess he's not a hedge fund guy, he's not a lawyer. You know, that's what I'm saying. He's just so, but ambition is important to me and hard working. So like it doesn't really matter. I mean Uber driver. I, I don't know. I, I need more information. Like I, it's less about the money. I'm, I make money, you know, I, I, I love this interview with Kiki Palmer when she was just like, what I don't need is a guy with money. You know, I want a guy that is going to support me and all these other great qualities. But I would never be with somebody who wasn't ambitious. Ambitious and hard working.
- [43:43]
Jared Freed
So that would be probably the best dating book for a man if it was like one page that explained every woman likes ambition and then the next page was just a workbook to write out your ambition, like to work on it, work on your pitch and like you'll be fine. Like just like. And then that was the whole book. Like just like lines on a page that was like, here's your, what's your ambition? And every year you have to come back to it to rewrite the new, you know, your lines ladder statement.
- [44:15]
Ashley Hesseltine
Yeah, I mean but it's, there's these, there's qualities not to get you deep that he has that are not, that are, that are non negotiables. You know, that are like he's a doer, he gets stuff done. You know, he is so not lazy. Like the opposite. You know, there's all these things that I had on my, you know, list that he ticked all the boxes that also my dad is, you know, so it's just, those are so, it doesn't really.
- [44:45]
Jared Freed
Except it was never cough and say slut. That's the only thing.
- [44:49]
Ashley Hesseltine
Well, he does that in the bedroom. That's her kink.
- [44:52]
Jared Freed
Ashley Hesseltine, thank you for coming on the show. Everyone, go watch the special. It's hilarious. It's called Here Comes the Bride at Ash Hess on Instagram. Go follow. Go follow. But go watch the special. It's linked below. We'll be back next week. Boom.