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It's a mailbag, Munder. You got problems there? I'm gonna help you from the comfort of my chair. It's a mailbag. Monday. Hello and welcome to the J Train podcast. This is Jay Train Jared Freed coming to you live from Delray Beach, Florida. That's right, every Monday is a mail bag Monday, where me the comedian takes you the listeners emails and we answer them. You might be new here because this is the week between Christmas and New Year's. Yes, we've entered into the timeless abyss where calories do not count and work does not get done, but time somehow stands still. And for some reason your podcasts have taken a week off. Your friend supposedly was like, ah, good luck during the week where you needed the most. Not your papa, jt, not your dear old uncle J Train. I'm here every day for you to put your brain on the shelf. Let me take the wheel. You got to walk. I'm going to be there with you. You got to drive. I'm going to be there with you. I ain't leaving your side. What do I ask in exchange for this? Tell a friend, a coworker, a brother, a sister, a mama, a papa, anyone who might need that in their life as well because they listen to a podcast that took this week off. Best of is not new. Best of the best of episodes are showing the worst of your favorite podcaster. This takes me 20 minutes. That's the promise. I'll do 20 minutes every weekday. That's my promise to you. We go longer usually, but I'm not going to under sell. I'm not going to oversell under deliver. I'm going to undersell over deliver every time. Yeah, part of the time on this show will be spent telling you that I'm the only one doing a podcast for you. Yeah, that's part of my 20. I have three listener emails here if you're new here. And I keep saying if you're new here because I know I'm a podcast listener. I'm just like you. That's the great reveal. Let me take off my mask Scooby Doo style. I. I've been you the whole time. That's right. So Monday we do emails. Tuesday we also do emails. Complaints. I take your complaints. It's ticked off Tuesday, Monday. All advice. If you have a question and you'd say, well, Jared, what the hell do you know? I'm going to answer thoughtfully. I'm going to answer curiously. I'm going to answer seductively your advice questions. And I'm not making Eye contact with you. That's a big deal. I don't ha. I get what you give me and then I give you my opinion with the biases that I have personally, but not towards you. Your friend knew you in college. Your friend saw you, you know, kissing the porcelain after a night of drinking. And now they don't. Eh. Well you're you. That's how they give you advice with. With. With pukey you. No, no, I know the you you email me with having a crisp ginger ale. Okay, so Tuesday we do so Monday advice J train podcast gmail.com Tuesday ticked off. Tuesday you complain to me. J Train podcast gmail.com Wednesday Chitchat. Wednesday I have a guest. We chit chat. If you have a guest you want to suggest, send it to jtrain podcast gmail.com Thursday pop culture Thursday I go to page six, I read the headlines and I riff. If you have a pop culture story you want read on this show, Jtrain podcast gmail.com Friday patreon. Five bucks a month gets you my personal diary. Coffee with J Train every Friday. This past Friday it. Well we're getting ahead because people do take vac, you know. Listen, I'm getting ahead for our producer V. So we me, we get we. I'm taping this Sunday, December 21st, 7:30 at night. What are you doing? 7:30 at night? Yeah, you're in your comfy cozies watching TV. I'm here working my ass off for you. Share the show. Share the show and if you're new here, subscribe just so it's there for when you need it because I'm always here as I just explained. So also YouTube, YouTube, YouTube. We are posting on YouTube v. The producer here is a part of the YouTube is doing a great job. We want you to go subscribe to YouTube, go watch. You can go take a tour of my parents house. You can take a tour of my new apartment in Delray Beach. You can see my favorite breakfast place, Sandy's. I'm going this Wednesday. Can't wait to go back to Sandy's. It's been a while. All right, last plug. San Diego. I'm in San Diego this week for New Year's Eve and the whole weekend. Philly, Baltimore, Atlanta, Charleston Beach, Mountain, North Carolina, Tampa, New York, Toronto. They're all coming. Vancouver, Tempe jaredfree.com the shows have been great. Just came back from Orlando. Love the Orlando shows. There was some weirdness. I'm going to complain about the Orlando show tomorrow on TikTok Tuesday and then I'll have stories about it that you'll, if you go to Patreon, you'll hear the stories about that weekend. So all the links are in the bio. I got three emails. I got one sponsor, support the sponsor. If they support you. That's the thing. That's the whole podcast game that I, I, I hate to keep reminding you, you, I'm not going to say you please use the sponsor. I'm going to say if the sponsor helps you, they help us. This show keeps on chugging as a train does. All right, all right. We're done explaining. I think the sound, if you're wondering, the sound should be better now. We got a new mic, new mic, new me. We're heading into a new year. I can't tell you how excited I am for 2026. There are some good things cooking in the JCU. I'm just, something's coming. I don't mean to be that annoying influencer, but you know, you guys listen, this show has its listeners. I, I meet you, I see you, I shake your hands, I kiss your babies. Where there's a good core group here. And I, I appreciate all of you. Thank you. Let me give some thanks. I've been thanking myself for putting this out every day, all episode. Hold on in, in the spirit of the new year. Thank you. Thank you for being a listener. Thank you for being a friend. Ah, Work for you. It worked for me. Once I got to the note, it felt good. All right, J train, sorry to clear my throat in your ear. J Train, I have a dating question for the wizard of haas. I'm a 37 year old single woman living alone in a suburban town where it's been challenging to meet other singles. I went for my annual eye exam at the same optometrist practice I've been going to for the last 12 years. Instead of the usual older doctor, I was seen by a new doctor who was very cute and not wearing a wedding ring. I mean, is that Hallmark movie or what? I mean, let me go back and read that paragraph because that paragraph read in a different tone. Like there's, this is kind of, this is. And if you're new here, I don't read the emails before I am reading them with you. But I do want to take a moment to tell you this is a lesson. And, and it's a lesson I have to tell myself. I, I was, I wasn't going to talk about this. I just, I've realized that your tone, if you, if you want to do like An I like, listen, I'm a curious guy. I like to do little test things and try things out. I think that's what makes I. I think that's like, curiosity is my new, is my 2026 mantra. I think people are better people when they're curious. Just be curious. I'm just, I'm pushing myself to be curious. And I think I had this, I had this question. I was like, if I go on threads, which is the new Twitter, Twitter I X, I may as well yell the yell my tweets into an empty cave. Nothing takes off, nothing gets attention there. I'm like, buried threads. You can get a reaction. I don't follow anyone on threads. I, I think, but I, I like to. What I've been doing on threads is I've been taking a really serious angry tone with stuff that doesn't matter. So I'll be like, if you think strawberry ice cream is delicious, you should just go and leave the country. Like, I'll say stuff like that. That is stupid. What I've noticed is you get that tone back, you'll have people that will respond like, well, you're a piece of. For I, you know, it's the, the tone matches my tone. It's weird. It's, it's interesting. You're like, oh, wow, if I stay happy, I'll find happiness. If I say, if I be negative, I'll find negative. You know, like. And it sounds stupid as I say it because I'm like, of course you do. But this is bringing me back to my point about your paragraph because you could read this so many different ways. I have a dating question for the wizard of the house. You could read it Sad. I'm a 37 year old single woman living alone in a suburban town where it's challenging to meet other singles. And I went for my annual eye exam because my eyes aren't great. I'm getting old at the same optometrist place I've been going for the last 12 years. Instead of the usual fuddy duddy doctor, I was seen by a new doctor who was cute not wearing a wedding ring. See how that that doesn't get me? Make me want to meet that person. Same paragraph, different reading. Ready? Jared? I'm a 37 year old single woman and I live on my own in this gorgeous upscale suburban town where it can be challenging to meet other singles. But there's so many people around and there's really great value in the place I live. And I have such a beautiful home. I actually recently Went for my annual eye exam at the same optometrist place. I love going to my optometrist. It's this older man who is just so sweet. And I've been going for the last 12 years. But this week, for whatever reason, the usual sweet old man optometrist that usually takes care of me wasn't there. And I was seen by a new doctor who was gorgeous. And uh, I happen to notice and you know, I don't really look for these things usually, but no wedding ring. See the difference? Do we see how much I want to hang out with one person? I changed a few words in each of them. Just make. I made one a little sadder, one a little sexier. But you feel that I think we. There's a lesson there. Okay, ready? During the usual. During the usual chit chat, he asked about my job, which led us to realizing we're the exact same age. And I used to teach at his alma mater. I know doctors in this situation are supposed to banter with patients and put them at ease, but I couldn't help feeling like we had a good vibe beyond that. Okay, good. And also, your feelings are not his problem. Your feelings of I had a good vibe own those. That's great. Is there a non weird way to put a feeler out to my optometrist? I already looked and can't find him on Instagram, but it looks like he has a LinkedIn. Can I message him there? Or is this all just way too creative daydream concoction? Or is this all just a way too creative daydream concocted during a routine exam? Please help. Whether it is or isn't, let's go Back to my 2026 mantra. Curiosity. Find out what it means to me. C U R I O S I T Y You will find a hot guy. Okay, I'm telling you right now, there is a line. You are not going to cross it. But let's prance up to the line. Don't go plotting up to the line. Go. You want to dance up to the line. You know he's on the dance floor. Okay? The optometrist is out there living La Vida Loca is playing on the speakers. You are looking. This is how you want to approach someone that you felt a vibe with. Come up vibing, come up dancing. Little little shake and happy and glowing and you know, be so happy that the only reason they turn you down is because their circumstances won't allow them to dance with you. Hey, want to dance? Hey. I saw you out here without a wedding ring, wanna, wanna shake a leg. And they're like, oh, I'm sorry, I got my wife here. I never wear a ring. And then they twirl them around. You go, no problem. And you dance backwards. I hope this is all painting a picture for you because is there a non weird way to put a feeler out to my optometrist? Absolutely. Let's be positive, let's be fun, let's be interested and be out there. Don't half shoot a shot. I have listen because I talk about dating, because, because I talk about being single on the Internet. I get shots taken at me. I am on the other side of this more in a. In a humbling way, like I am. And I. And it's not because I'm so great. I know this. You might go, jared, you're being too humble. I'll allow you to feel that way. I am telling you what I truly believe. I get people shoot their shot on me because I am a safe adventure. I. I am someone talking about being single. I am someone speaking about relatable things. And if I don't get back, oh, he doesn't see my message. Oh, it's okay. So I get a lot of like half shots. I'll never get back to a half shot. I'll never take interest in a half shot. It will always scream danger to me. It will always put us on two different levels. I need to know the whole story. If I'm you, I go to LinkedIn. I say, hey, I really enjoyed our conversation the other day. I don't want to cross any patient doctor boundaries that I don't know anything about. You know, reference the, the, you know, let him off the hook. I don't want to put you in any awkward position, but I would love to get a drink sometime if you're up for it. Here's my number. Get to me if you want to make it happen. So leave him all the tools to make a date. His your number, what day you're open. Hey, it's holiday time. I know the first week of the year is pretty dead for me. It might be for you. Would love to get a drink the first week of the new year. If you're up for it. Here's my number. If this is totally not something you do with patients or people you see in your office, I'll totally understand. Let them off the hook. But come in positive. Hey, I really enjoyed talking to you the other day. Would love to get a drink sometime. I'm free next week. Here's my number. Make a plan and I'm in. Done. He has all the tools. He knows you want to go. You have let him off the hook. He can say hey. You've given him the excuse he can take. You don't need an honest response. You don't need hey, I'm not into you. You don't no, no, no. You need no thank you or nothing. That's okay to leave it at the door like doordash. Leave it at the door. J train podcast@gmail.com J train podcast gmail.com we're sponsored. Love this sponsor for the new year, Rocket Money. This is something that can help you organize your finances. I think this is one of those sponsors. I'm speaking to you genuinely. This is a sponsor that helps you and I like that. Especially with finances and organizing them. I know that can be that's hard for me. The new, the new year is here. It's great. Time to check in on budgets. Keep an eye on your spending patterns with Rocket Money. 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Oh, what was that? Rocket Buddy, go to the the bio. Here's a question. This was sent as a dm. You can DM your questions to the J Train Instagram account where we put all the J Train Instagram account. If I'm going to like go to Plug City for a second. Great way to be reminded my show exists. I'm not sitting here believing you're going to listen every day. That's why I kind of like this week. I do this week of episodes. You know, I say to you that a podcaster doesn't really care about you because I don't really think they care about themselves. I think this is a great week to, like, find new listeners. I also know that a month from now, you might not be in the mood for my voice. I get that, too. Subscribe to the J Train Instagram account. You'll see the clips that come up. Maybe there's an episode. Oh, okay, I'll go, I'll go listen to that one. I'll go watch that guest. So also, we take questions from the DMS in the at J Train podcast. So if you subscribe to that channel, the only way we answer your DMS is if you're following. So here's a dm. If a guy's trying to go further on a fifth date and you turn him down, then he doesn't text the next day. Is his ego bruised or was he only ever after one thing? Should the girl ever message as it feels weird just leaving it at nothing. The dates and connection had been good. I like this question because listen, there, there's, I, there's a lot here not being said, but let me go to the, the brick and mortar of it all. Fifth date, you say you don't want to be more physical than you're being, and then he doesn't text the next day. That is a win for everyone involved. And I mean that in the land of not extremes and because bad things can happen. You know, I, I hope this was as it's in my mind when I read this. Is there two adults that, hey, you know, I, I, you know, one's kissing and the other's going, I'm, you know, listen, I just think tonight's not the night for me. This is all living in the land of we have two consenting adults. If you're going to extreme places or, you know, because those things can happen. So I, I'm, I'm flubbing a little bit because I want to make sure that you know that I understand that, hey, I turned someone down on a fifth date. They didn't go further. The languaging is a little bit, you know, can get us into uncomfortable places. I'm staying in the fat part of the bell curve where two people can be in the, the heat of a makeout and one is ready to go upstairs to their apartment. The other says, it's not for me. Let's live in that world. Now you turn them down the next day. I think this is a win for both parties. Okay. And I'm going to give you your side. You turned him down. You said, this is what I want. You have revealed that next level of intimacy is only reserved for very important people in my life is only reserved for people I am going to have more of a future with. That is what is said to me when you stop someone from coming upstairs, so to speak. That is a win. You have told someone what you wanted. You were honest. Whether you were honest or not, hey, don't come upstairs. That is communicating. That is saying what you want. Now what? The problem that happens from my end is if you say, hey, I don't want to go upstairs tonight. That's not for me. Some people use that against you. They'll go, well, I didn't say I wanted to get married. I don't. That's not the message you are giving. And which is totally fine is getting intimate. Getting more intimate and physical means something more to me. And I need to be sure about that. That is fine. From his end, he has been told that, hey, this means more to me. I am not looking for casual intimacy or with someone, okay? Now both sides go back to their apartments, their side of the, you know, the boxing ring. You go back to your side and you go, ah, I hope he likes me. I hope I get a text the next day. I hope we go on a sixth date. I hope we can extend the relationship to get to know each other better so that I am ready for that type of intimacy. He goes back to his side of the ring and he goes, do I want that level of intimacy with this person? Do I want to get more serious? Do I want. And do I want to lie to someone? Do I want to say that I'm getting more intimate? But it doesn't mean as much to me because I know that I can be physical with someone who I'm not serious with. Do I say that to them? How honest do I be? And a lot of people, they go, you know what? I'm going to end this here, because I can't get to that place that they want to be or I assume they want to be. I think that's a win for everybody. We all kind of. We all showed who we were in that moment. He showed that he was looking for casual intimacy with someone. Maybe it would have gone further because then what you do, and I think this is a problem. You try to separate this, and it's a problem that's very human. You're trying to separate this into ego, bruised, or he only wanted to fuck. He's I don't believe the ego bruised. I think that's like, not even an answer. That's not something I've. I've gotten turned down. And I don't go, oh, oh, how will I ever look at another woman in the eye again? I can't believe she turned down Papa JT with my huge. I can't believe it. That never happens to me. I never, I've never had that feeling. I've never had that feeling. If I've never had that feeling, I don't think it happens as much as people believe because I'm not that abnormal. So the ego bruise thing, I think that's something that we have been taught from movies, and maybe that's how maybe men show themselves, but I don't think it's a real thing. Maybe they, you know, I, I, I just, I. Maybe it's a real thing. I'll give the credit of real thing. I just don't. It doesn't speak to me. Was he only after one thing? I, I think that vilifies him in a way that dehumanizes the other side. The other side, which I have been. So what you're doing. If someone said that about me and said that I. When I wanted to go up to the my apartment with them, and then they said no, and then I didn't get back to them, and then they were like, he was only after me, that wouldn't feel good to me. So I would say that's not how I felt in those moments. I have felt I like this person. I was happy to go out with them. They. I saw how they felt in this moment about being physical and being intimate and getting to know someone and what their level of comfort was. And I am saying, I don't think I can get to that place, and I don't want to be. I don't want to, you know, be with someone that we're not on the same page. So I'm gonna opt out. That's a more real answer. That's an answer that's tough to say to someone too, hey, I really like you, but I don't see a real serious relationship at this point. And I would have hooked up, but I'm now seeing that that's an important thing to you. So I'm not gonna, like, go down that road with you. And, you know, the choice becomes from his end and the choice he's making is, do I go home and masturbate and not disappoint anyone, or do I go forward with this woman who has just told me being physical with them is important and they don't want to be with someone and have it be casual and feel like I'm lying to them. He chose masturbation and I think there's something to be commended. Now could he text you, hey, I just want to let you know I had a great time, but this isn't a relationship for me. You would have to be trusted. And I I my message to you. If he does send that text, he hasn't yet. That's. That sucks. He should. If he hasn't done that. If he did send that text, you have to go, I get it. That's not. Because that's not as personal as it as it maybe might feel. J train podcast@gmail.com J train podcast@gmail.com I got a question and happy so this one has. So I guess you wrote in last December. I have the question from so V Did a great job here. So they sent a question December 2024. It is now December 2025. Here's their question from December 2024. My mailbag Monday question is about relationship advice. I've been seeing my boyfriend for six months and this is my first serious relationship since my divorce nearly six years ago. I've realized I've fallen in love with him, but I know I But I don't know how or when to say it. I haven't told a partner I love you since 2014. I'm scared to say it out loud even though I don't need to hear it right back right away. Let me read that sentence again. I'm scared to say it out loud and even though I don't need to hear it back right away, even though. Hold on. Okay. I've realized I've fallen in love. This is from I Up. This really nice email. I've realized I've fallen in love with him, but I don't know how or when to say it. I haven't told a partner I love you since 2014 and I'm scared to say it out loud even though I don't need to hear it back right away. I just don't know how to be that vulnerable again. Thank you for reading. Love the podcast. Hope to catch your show next time you're in Utah. Anxious Anonymous in Utah. Okay, so that was their email in December 2024. Now we have a follow up, which I would love. More follow ups. Feather Feather, Happy holidays and a peaceful new year to you and yours. Last December, I wrote to you asking how and when I should tell my boyfriend that I love him at that point. We've been together six months, and it was my first new relationship in a decade. Well, I told him, and I didn't expect him to say it back, and he didn't at the time. But he did get there a few weeks later, and it was worth the wait. We've now been together a year. We've now been together a year and a half, and it's going so well, I could die. I just wanted to write and say thank you for all the laughs and good advice. J Train is an invaluable part of my morning routine. Getting up for work is a slog, especially in the dark winter mornings. And your show makes it easier to drag who I ass out of bed. I listen as I get dressed and ready for the day, and it's been the best way. Oh, to start the day with a smile. Hope to catch you next time in Utah. I'm, I'm, like, getting emotional reading that. I, I'm trying to hold back from crying a little bit. This is so beautiful and nice and y', all, I, I guess this is a great way to end the year. You know, this is December, the week of the 29th, the week of the last week of the year. We're here in J Train. As I said, I'll be doing all week. This makes me feel so good. I, you know, I, I, I don't want to ruin this beautiful email that's making me emotional, but to speak honestly with you, the listener, when I started doing podcasts and started doing comedy, it's a selfish motivation. I love getting a laugh. I love people liking hearing a story. I love, you know, when I first started, I was like, I want to tell stories, and I want to make people laugh, and I want to make a living doing it. That was the goal. And, you know, because, you know, your goals and I, I think, you know, a mix of reality and art and passion and all that stuff, because I'm a react, I'm a realistic person for the most part. I have my own delusions, my own dreams. But I, I do a big part of what I do is try to keep it real with myself, even though keep it real sounds really douchey and not real. But it has been the most unexpected pleasure to hear back from people, stuff like this, just being there. And I say, take your brain, put it on the shelf. Being there in these odd moments that you're by yourself, you're in the car, you're doing the dishes. It is. And to hear it back. I never really, I didn't get into this for that. I don't mean to sound whatever or to ruin a compliment. I'm bad at receiving compliments. I'm better receiving gifts. But I will say this show gives me so much value, so much love, and I love answering the emails. I, you know, answering the two that we just did. Like, I truly feel great doing it. So what an added bonus. What an amazing, beautiful thing to connect with people all around the world in this way. So I just want to say, you know, thank you to this emailer for the beautiful words and I'm so happy the relationship's going well. When someone says, you know, hey, I listen to the show and you help me with my issue and I'm not even doing anything, I'm just saying, saying stuff out loud that anyone would say and hopefully I make it funny, that's like my, my dad and how about you make it funny? You know, that would be. My dad would say that. But, you know, and hopefully there's a laugh here to be found. But, you know, as I vamp and go on and on, I mean, we have hit the 30 minute mark. So I'm not worried about the promise that I made at the beginning of this episode. You know, I used to have guests on every episode and then the, the show changed a little bit. It, it's changed over the years. It' but when I had guests on, I would always say to them, answer the email first. You'll go, you're going to be funny. You'll find a way to funny. We'll have our fun. But no, you are, your only real responsibility is to answer the email and then your glowing great personality will be shown through that. And I've tried my. And that's always been kind of the, the rule here on Mailbag Monday and with, you know, this podcast and you up as well, and I've taken that mantra into you up. So, you know, it's really cool to hear back like this. So listen to everyone out there. Be safe. Have a great new year. Thank you, thank you, thank you for being a part of this show. Back next week, boom.
Host: Jared Freid
Date: December 29, 2025
In this “Mailbag Monday” edition, Jared Freid answers listener emails on dating dilemmas, vulnerability, and relationship boundaries. Broadcasting solo from Delray Beach, Florida in the final days of 2025, Jared not only addresses the main question—should you shoot your shot with your cute optometrist?—but also weighs in on navigating intimacy timelines and reflects on a listener’s journey to saying “I love you” after divorce. Delivering insight, humor, and a signature dose of empathy, Jared’s tone ranges from playful to sincere as he guides listeners through their tangled love lives.
[07:00 - 22:30]
Listener Question:
A 37-year-old woman wonders if she should try connecting with her attractive new optometrist after feeling a potential “vibe” during her exam. She asks if it’s weird to message him on LinkedIn, since she can’t find his Instagram.
Jared’s Advice:
“See the difference? Do we see how much I want to hang out with one person? I changed a few words... just made one a little sadder, one a little sexier.” (11:45)
"Let’s go back to my 2026 mantra—curiosity. Find out what it means to me: C-U-R-I-O-S-I-T-Y. You will find a hot guy.” (15:10)
“I’d go to LinkedIn. I’d say, ‘Hey, I really enjoyed our conversation the other day. I don’t want to cross any patient–doctor boundaries ... but would love to get a drink sometime if you’re up for it. Here’s my number… If this is totally not something you do with patients, I’ll totally understand.’” (18:20)
"I'll never get back to a half-shot. I'll never take interest in a half-shot. It will always scream danger to me." (16:59)
Tone & Encouragement:
Jared uses a “dancing on the line” metaphor: come to the “dance floor” ready for a good time, make your interest known, and allow people an easy way to decline without discomfort.
[24:55 - 33:35]
Listener Question (via Instagram DM):
A woman asks why a man didn’t text the day after she declined to go further physically on their fifth date. Is he just after sex, or did his ego get bruised? Should she reach out?
Jared’s Analysis & Advice:
"You turned him down… That is a win. You have told someone what you wanted. You were honest." (27:02)
"I've gotten turned down. And I don't go, 'Oh, oh, how will I ever look at another woman in the eye again?'" (29:20)
"He goes back... and goes: Do I want that level of intimacy with this person? And do I want to lie to someone? He chose masturbation and I think there's something to be commended..." (30:40)
[33:40 - 40:10]
Listener Background:
A year prior, a listener wrote about nerves in saying "I love you" to her new boyfriend, her first serious relationship since divorce.
The Update:
She did tell him, he didn’t say it immediately, but did a few weeks later. Now a year and a half in, the relationship is “going so well, I could die.”
“Getting up for work is a slog, especially in the dark winter mornings, and your show makes it easier... I listen as I get dressed ... it’s the best way to start the day with a smile.” ([Listener email], ~35:00)
Jared’s Emotional Response:
Jared openly shares how much these kinds of follow-ups mean to him:
“I’m, like, getting emotional reading that. I’m trying to hold back from crying a little bit. This is so beautiful and nice ... what an amazing, beautiful thing to connect with people all around the world in this way.” (37:15)
Reflections on Podcasting:
He speaks candidly about the unexpectedly meaningful feedback from listeners over the years and the pleasure of helping—originally just wanting to make people laugh, but now cherishing the genuine connections.
On Positive Framing:
“If you stay happy, you’ll find happiness. If you be negative, you’ll find negative… It sounds stupid as I say it, but of course you do.” (12:30)
On Making a Move:
“Don’t half-shoot a shot… Come in positive. Hey, I really enjoyed talking to you the other day. Would love to get a drink sometime. I’m free next week. Here's my number. Make a plan and I'm in. Done.” (18:30)
On Intimacy Boundaries:
"That is communicating. That is saying what you want… That's a win for everybody. We all kind of—we all showed who we were in that moment." (26:55)
On Audience Connection:
“Being there in these odd moments that you’re by yourself… That is—what an added bonus. What an amazing, beautiful thing to connect with people all around the world in this way.” (37:30)
Jared’s style is friendly, energetic, playful, and candid—quick to poke fun at himself and others, deeply empathetic, occasionally poignant. He balances humor with practical advice, always returning to the importance of self-respect, clarity, and vulnerability in dating and life.
To write in for advice:
Email jtrainpodcast@gmail.com or DM @jtrainpodcast (follow first to have your message considered).