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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 you, the listener, email me, the comedian, your advice questions. That's it. That's the show. I have two questions in front of me. They are longer, which I would assume means thorough. I read them with you. You're hearing them the same moment I'm hearing them from me reading them. That's a weird way for me to say it. I'm just saying I read. But I know today's are good because V. The producer of this show already texted me, like, I think there's an interesting one that you're going to disagree with. That was the hint I was given. So very much looking forward to these emails and getting into them. We. We need your emails. Your emails are what make this show great. So I want you to send in your email to jtrain podcast gmail.com, any type of advice. It could be just something that's on your mind. You were thinking about something, you ran into a situation. Should you have handled it differently? Am I the. All those things that have become things, you know, back in the day was just email the show. I mean, back in the day, I'm. I feel I'm a hundred years old. I've been doing this show a long time, maybe 13 years at this point. So, yeah, I've been taking these emails for a long time. And you. You might be new here. Maybe you just clicked on my Instagram stories because I post these every day. And you thought, now, give it a shot. Why would I ask you any questions or for advice? Well, people have been sending them in. I. I've never run out of questions, which. That's a comment in itself. And, you know, I don't have to make eye contact with you when I answer these things, so you can confide in me. I've never released any names or made anyone feel, you know, I. I make sure to keep these emails between you and I, and then we read them and no one knows who it is. So you can hear someone say out loud the things they would say behind your back. Whoo. Sometimes I say a sentence and I'm like, that felt good. That is exactly what this show is, me telling you to your face, what I would say to someone behind your back. If we were discussing your Issue. That is what this show is and. And me start. I do this on Patreon a lot. But I want to make sure I thank you for listening to this show, for being involved in this show. I just did a private event in Hollywood, Florida. I'm taping this on Monday morning, the week before this comes out. And there was a. A. A man and his wife. A man. It was a guy, you know, around my age or younger, a little bit. He looked a little younger. He came to the event because he saw that I. And it was a private event, but they put out the word to the people that followed them. It was a, you know, a charity event. And he's like, I've been listening for years, and you're always out of town where, you know, you're in town when I'm out of town. And I. And I was like. And I was seeing him and his wife enjoy the show. I could, I, you know, when I'm on stage, I can tell who's enjoying and I can tell who's, like, a little bit more reserved. And they were enjoying. They were just having a great time. And I. It made me so happy. And he came out and I noticed him during the show. I said, I noticed both him and his wife or girlfriend or whoever they were, and he came out to me and said hello, and we took a picture. But he was like, I listened to the advice and ticked off Tuesday. And, you know, those were the flavors of the J Train cinematic universe that he enjoyed. And it made me so happy. So I just want to say thank you for listening and enjoying this show in any way you do. If you have a. If there's a situation here that relates to a friend of yours, I'm going to ask you to share it. But there's so many different ways to support this show. If you're getting value from it. Are you getting value from it? I hope you are. I do. I get it on my end. Just even that interaction last night made me feel so good that he. He likes the podcast, hadn't seen me on stage. I'm at this weird charity event that I'm going to talk about on Patreon this week, or it'll be last week. I'll. I'll have already talked about it. So if you're listening right now, I'll talk about doing the charity event, which was weird and fun, and it was great. It was great. But the charity events are always, you know, for me going in, it's a little bit of a mind. It's tough so I'm going to give my full kind of what was going through my mind going into the charity event so you can sign up for Patreon. That's a great way to support this show. It's five bucks a month and it gets you the Friday episode. I hate the word support. If you know me on this show or this platform for any amount of time, the word support feels like donations and things like that. There's no, we're doing each other, you know, this is a, you know, this is a product exchange for services that, you know. If you want to pay for this show, which is free, I put it out in good faith that you're going to find a way to pay for it. Here are the ways to do it. Join the Patreon. 5 bucks a month that you know, then that's. I mean, to me, that's amazing. That's. You're paying for something that you know, the Internet's a free place. Share to your stories on Instagram or, you know, like it on TikTok. Like it on Instagram. Follow the Instagram profile at J Train Podcast. Email the show. That's a way to support the show. The sponsors. We have two sponsors today. The sponsors are always going to be in the description of the episode, always. So you can find the promo code and the free money that they give you. That's a big old circle jerk. I'm jerking you off with a promo code. They're jerking me off with some cash. You're jerking them off with your business. Big old circle jerk. Yeah. That was a weird way to describe it, but I think it actually does the job. So that is all my announcements. Otherwise, Kansas City. I'm on the road. Kansas City, Richmond, D.C. milwaukee, Min. Minneapolis. Those are the cities coming up. I've added a Boston show. You can go to jrfree.com for the tickets. So we'll do email. Ad, Ad, email. I think that's the best way to play it. So let's get into it. Those are all the. Oh, and YouTube. I'm trying on YouTube. I mean, the shorts are starting to do better. YouTube shorts. But that's, you know, there's like five of you who know what I'm talking about. Some of you marketing people. Jared, big fan of you. The you, a podcast and J Train. Thank you. I actually discovered you back in 2022 on Spotify during your dating makeover era, so. Dating makeover. I thought it was a good idea. I don't think that they were organized enough. If I'm to be Honest. Spotify had a live version where, you know, you could listen live. And there were shows that they created. But the Spotify Live thing was an app that was separate from Spotify. Then they merged it onto Spotify, which it always should have been from the get go. It should have been Spotify Live. This is what's happening now. As if it's like real radio. So it never really got together, but there were people that really loved that show. People. Basically every Sunday night I would take calls and give advice and it got personal. It was tough to get people because you could just sit and kind of watch. You could be a lurker, which is totally fine. But it was hard because I'd be like, hey everybody, who's got questions? And I was like hired for an hour every Sunday night. I love doing it. I wish they would believe me. I wish they did it again. It was good money too. Can't wait to see you in Houston for the first time in February 2026. Well, I'm excited for that too. I'm a 26 year old woman with a massive crush on my 47 year old male coworker. Okay, I'm reading this as you're hearing it. All of us had the same thought. 26, 40, 47, that's an age gap now. Can that happen in a world? Anything can happen. So I'm not sitting here to judge 26 versus 47. I mean it does look like father, daughter. At some point it could look like I, I don't know. You don't know? I'm just, I'm was. I'm sure there's someone listening right now who's disgusted that I'm even entertaining. This is a possibility. And you're wondering, is the 47 year old married? Have they ever been married? You're wondering what is wrong with the 47 year old. That's kind of my first thought. That's where my brain goes. So I'm assuming I'm not crazy and your brain. And that's not fair. I'm 40, never married, no kids. If a 26 year old, I'm talking to this 4 year old guy, you might have that thought too. I think I would. I'm just saying on paper I, you know, I'm 26, I have a massive crush. Well, also she has the massive crush. He might just be being nice, which is also a possibility. We work in the same office, but different departments. I've been at my job about a year and a half. We don't interact much, but we see each other a few times a week. At first I thought he liked me because I'd catch him looking at me and turning away. Okay, okay, we're. We're. We're entering into, you know, it's. I need more than that. 47. And I listen, I understand. There's vibes. There's such a thing as the atmosphere and the weather, and you do feel eyes on you. And if you're feeling that, I'm sure it's. There's a version of it that's true. Does that mean. Does looking at you from across the, you know, 47 year old. You know, this sounds creepy, but, like, I got this hot 26 year old that works, you know, in my. That's in a different department, but same office. And he checks you out? Yeah, I mean, like, that's always like the thing with, like, old men, you know, like, oh, look at this cute grandpa. It's like that grandpa's as gross as. As the guys you're dealing with. Like, I don't really buy the idea that you age into cuddly. Like, I've been in my job about a year and a half, and we don't interact much, but we see each other a few times a week. At first I thought he liked me because I'd catch him looking at me and turning away. Once he walked with me to the cafeteria and asked about my job. That was our longest convo. Here's what I would say to you. Currently, you have nothing. You don't have anything. You have someone being nice to you, and you have an attraction to him. So you're building it up into more than it is. So far, I haven't read the rest. I've also noticed him hanging around near my side of the. I've also noticed him hanging around near my side of the office, though. Never talked, though. Never talks to me. Then this new older woman started, and he's obsessed with her. And then she puts an eye roll emoji. They chat a lot, and I get jealous. I wonder, are they screwing? Does he prefer older women? Is he trying to make me jealous? Meanwhile, I don't really give him attention either. I don't make eye contact, don't say hi. Not because it's him. I'm just quiet, shy and introverted. Maybe that's why he doesn't approach me. Okay, so far my feedback to you is you've invented something into more than it is based on what you've written. I do. Listen, I'm gonna believe you and say that. Yeah, this guy was checking you out. I, I think that is like a normal thing to feel to see. You know, and, and that's energies and all those things. It's like I think this guy and also then you kind of get it in your head, is he checking me out? He is kind of cute, huh? I never thought of myself with an older man. And then you start and you know the betches Jordana, they came up with the term emotionally masturbating. You're kind of emotionally masturbating to the idea of older guy who's got his all his life all set. I can understand how you're getting to where you're going, but when the minute you start saying the way you wrote it is like without having more than a. I'm giving you a lot of empathy. There's someone that's listening that's like this, this chick is nuts. I'm not going to call you nuts. I'm not going to do that. I'm going to tell you that I think you've gotten carried away with a storyline based on being attract to a guy who hasn't given you more than you know. Your longest convo was how what's your job like on the way to the cafeteria. You got nothing here. And him looking at you in the way, you know, I mean that I, I think this is proximity. You're in the same office, you start to, you know, this is based on surroundings more than you actually like him. So I, I, I think when you write, they chat. You write. And he's obsessed with her. That's not true either. This new older woman started and he's obsessed with her eye roll. Like let's say he's, they have more in common and they have more to talk about. The idea that he's upset. It's not love or hate. I checked her out because she's cute. I didn't check her out because I'm in love with her and think there could be a future in a relationship. You're dealing in extremes. They talk more than they talk than I talk with him. So that means he was obsessed with her. No, that's not necessarily what it means. And again, I'm not there. I'm just, I'm taking your words and making assumptions. Yes, I know the ro the office romance issues, but it's not like I want to marry the guy. See, you're already demeaning how his, his feelings on this. Demeaning might be the wrong word. You're already downplaying. You're saying it's no big deal. And this happens a lot. I've noticed. There's no like men, people let me, let me not gender this. When, when we're talking about ourselves we always think it's me. I'm the cool one, I'm chill. Never. You never think of yourself as the worst version of you. What do I mean by that? I'm trying to explain it better. Like most men when they approach a woman, don't think about a woman thinking of a guy as their biggest threat. That whole bear versus man conversation was built on men not realizing that they are as big a physical threat to a woman than a bear. Which I get the joke. The reason men got angry at that is because they didn't know what was being said. They didn't even, they didn't, they, they sounded stupid. Men who got mad at the bear versus I don't even know if any men got mad at that. I just think that we've recreated this person that's all angry that like how could you compare? You're more afraid of me than a bear. Like that was a whole conversation. And to update you if you're wondering what I'm talking about, there was this whole thing of like would you rap, you know, like where women were asked would you rather, you know, a bear or a man? And like they were basically saying the bear is less dangerous than the man type of thing. And men supposedly got offended by that. So I'm saying you're kind of doing the same thing as those men that were put it, that got angry at that supposedly. So you're not really looking at like you're, you know, you, you're saying, yeah, I know the ro Office romance issues, but it's not like I want to marry the guy, you know, and it's like, well, hold on. From his end, you're a young woman who. And he's 47. And, and again you've talked once so he has no idea maybe that you even are thinking of him in this way. But let's think, let's say he is attracted to you and he hasn't made a move. Well, he hasn't made a move because it doesn't really look great for a 47 year old to try and pursue a 26 year old generally. It doesn't really look, it looks even worse to do that at work. It looks even worse if he is in a position of power and you and, and could be, you know, all those things. So you are dangerous to him. And I know you're writing from you're the star of your own movie, so you're going, it's me, it's cute me. I'm just looking a fuck. He is not assuming that, not one minute. Is he assuming that she writes. He's not even my type. Just something new I want to try. Do you see? I, I, I think you're. I, I think you're. First of all, again, this is based on. You've had one sentence of conversations and that's it. So you know nothing more. It's not like you guys went on a date and he confided you and there's none of that. So just something new I want to try. You're, you're in a fantasy world. He's a silver fox, I'm black. And if anything happened, it'd be my first time with someone older. Honestly, I just like a few dates, maybe hook up and see where it goes. You are so far ahead of yourself. But why hasn't he made a move yet? Am I not his type? I don't want to aggressively show interest. I want to be pursued. I don't want to feel desperate. You got to walk before you can run. I think there's a lot of issues in that, that, that paragraph. But why hasn't he made a move? Well, you guys are at work and you've only noticed that he's like, looked in your general direction. You've spoken once, so that's why there's, and then I. Am I not his type? I have no idea. You don't have any idea? I don't want to aggressively show interest. I want to be pursued. I think you've turned this person into a fantasy is my feedback. I don't think, I think you, it's nice to want to be pursued. You are not being pursued by this guy. And I would, you know, chew on that and see that as, okay, maybe I'm, I'm not as turned on by him. This is a turn off that he hasn't pursued me. But also you're at work. Like you can't poo poo the work thing. And I'm saying this as a man, I think the idea that you could get in trouble at work is like way more on the mind of a lot of men. There's no romance here. Like, he's not thinking of, like, what if we make it? What if we are the ones for each other? Earlier this year, another older guy visited my job. More my type. Divorce, no kids, high career level. I followed him ig, but he never accepted. So I deleted the request embarrassing. It's not embarrassing. It's not. I can't tell you how to feel, so I can't tell you to not feel embarrassed. But the idea, hey, I saw a guy at work. I followed him on IG and then he didn't accept. Fine, you took your shot, didn't work out. No one's going to judge you for that. I would. The judgment would be more that this is a continuous pattern with you of going for work people. And again, you're not really acknowledging the fear from the other end. You're just saying, it's fine for me, so it should be fine for everyone. And I disagree with that. If he was interested, he could have said something before leaving. How can I show interest without making the first move? Was the IG follow enough? I think the IG follow is a good beginning. I think when you say, how can I show interest without making the first move? I think you got to get away from the people at work. I think that's kind of in your way as far as, like, mentally. I remember you saying, a follow and a like is enough for a guy to get the hint. Yeah, well, how about they said no and that's okay. Shooting your shot doesn't mean every shot goes in. I've been single way too long. Again, you are putting judgments on yourself that no one is putting. I've been single way too long. What's too long? I don't believe in too anything. You've been single and you'd like to make a connection with someone. If I were you, I would be more intentional. Right now. It's a lot of passive stuff. And you're thinking that any intentions of dating and putting the work into dating and. And making any type of effort means that you're not going to feel pursued. I think you can make effort with dating while also feeling pursued. Hey, it was really great meeting you. I'd love for you to have my number. Then they either pull on the string or they don't. You can feel pursued and also be intentional about dating. I think you have separated the two so much that you're waiting for this, like, kind of like erotica, fan fiction, version of love that doesn't really exist. I feel like I wasted my 20s not dating. I don't think. Again, these are judgments you're putting on yourself. No one is doing. I'm 26 now and working on myself. Weight loss, stabilizing life. But I also want to get out there and have fun. Should I wait until I reach my goals or just Start dating now. There's a lot of questions in this email. I do think in addition to everything I've said, you should go talk to a professional. I think you're putting a lot of your worth in other people's hands. And like, I don't, I wouldn't want that from me. I try not to do that. I'm saying a professional would be more helpful and have the tools to help you through a lot of the things that are written here. Because there's a lot of mixed things going on. There's the, you're, you're going down the road of being jealous of someone else who's talking to a guy who you've talked to once at work. You're seeing a Facebook request or an Instagram request to follow, not being acknowledged as some sort of failure and embarrassment. All of these things. I don't believe so. And then you say, I've been single way too long and I want to be pursued without, you know, I don't want to feel desperate. I think the word desperate, if I'm to give feedback whenever I hear people, I don't want to look desperate. I don't want to. I feel like that's a really self conscious thing because most people don't come off as desperate. Most of the things people talk about with being desperate aren't desperate. I can't believe I asked. I, I follow him and I, I tried to follow him on IG and he didn't respond. I, oh man, I, I hope I don't look desperate. Not at all. You met someone at work, you thought they were good looking. You went to follow on Instagram. It didn't work out. They have their own reasons that are not as evil on angry or extreme as you're making them out to be. I think this is all way more in the middle. I think this email lives in the land of extreme. I would have, I think I'm not a professional. I'm just someone reading an email and I'm happy you wrote in here, but there's a lot going on here. I think a professional would help you. I think also, you know, I feel like I wasted my 20s not dating. It's not a waste. You can date anytime. I, if I were you, you say, should I wait until I reach my goals and or just start dating now? I would be more intentional. Again, I keep coming back to that word, intentional. What does it mean? I think creating a dating app, profile, putting your pictures together, making, you know, answering the prompts, getting some likes on there and having some interactions with people that know you're there to date. Because that's the beauty of a dating app. It's for people. It's you're under the roof of I'm here to date. And that gets you on more dates so that you can develop taste. Instead of playing this game of like, I'm happy because this guy likes me, you're playing if they like me, then I feel good. And that's not a fun game to play. J train podcast gmail.com j train podcast@gmail.com nutrafol if bad hair day is turning into a bad hair decade, it's time to try Neutrophil. 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I Love this. I'm 46, female, in Bend, Oregon, and it's slim pickings out here, and I'm hoping to find a partner. Bend, I think, is where the University of Oregon is. It's. It's. It's in the country. I'm about three weeks in with a new I'm about three weeks in with a new guy who seemed really cool so far, but it would be long distance. Haven't met yet. Okay. I'm already thinking you're ahead of yourself. You gotta meet. I understand three weeks. You're not three weeks in. You have connected with someone you're yet to meet. We connected on the apps when I was traveling in his area for work. Let him know right away I wasn't from there, but he was interested in continuing the conversation. Didn't have a chance to meet while I was there. Bad signs. That's okay. I think it's okay to change your location. It's okay that you let them know. Didn't have a cheat. You gotta meet quick in these scenarios because the odds are against you. Didn't have the chance to meet while I was there, but have had great texting banter. Okay, that's fine. That's good. Great texting banter is like less good than in person banter. So it's something. But it's not everything. And it's not to mean that it's going to be great in person. You you've never met, Let me remind you a couple of fun long phone dates and fairly firm plans to meet up in October. Long phone dates, Fun, great. Still not in person. October. I'm reading this September 8th. We got a while. So there's a lot of chance to get ahead of ourselves. Knowing the person that has been written down on a piece of paper, that's a thing. When you're texting, you get to write your own script. You get to be who you want to be. You get to be the person you would write in the movie. It's not the real you. It's not the you that reacts right away. They're not seeing what you think right away. You get to google things to make yourself sound like you know more than you do. So the texting you is not the you you. The texting you is the glorified, beautiful version of you that you would put in the ROM com. You are not a rom com character. You are you. You are boring. You. You are reacts weirdly and awkwardly to things that you wish you didn't. React weirdly and awkwardly to you. We have a fairly fair and you said fairly firm plans to meet up in October. Not when I've not met someone. Nothing's firm. You owe them nothing. They owe you nothing. That is, until the attached text message exchange this afternoon. He's currently working on a move from Denver to Boulder and said he was moving some plants today and then said he would be chilling by the pool of the new place before going back home and sent me the attached two pics I noticed from the reflection in his sunglasses and that there was a woman sitting in the chair right next to him. My God. I asked him who he was hanging out with and the more he responded the weir it got, and the more he responded, the weirder it got. I think it's over. But what do you think? Is this totally suspicious or what? Anything he could say that would make it fixable. For one thing, when you look at the reflection, the woman is obviously sitting in his right. But when he sends me a picture of the empty chair, it's obviously to his left. Why even go through the bother? Ugh. I await your ruling with anticipation. Okay, so let's go look at the text. So he sends a picture of the pool, then a selfie and then the reflection. So here's the picture of the pool he shows the selfie. We're not going to show the selfie, but we'll show the text on the Instagram. Nice. Who you hanging out with? And I like that you came in, you know, you played, you did a little Matlock. You were like, I'll play it nice and stupid. But I saw something he wrote, nice smiley face. Who you hanging with? He writes, myself drinking a brew. Need to take some pictures of art I'm going to sell and roll home, but way comfy right now. So this guy is chilling. Little does he know he made a huge mistake. Gotcha. Just looked like you were sitting kind of close to someone on a half empty pool deck. Figured you had company. Enjoy the rest of the afternoon. So right now she's making it very clear. I have seen something. I'm feeling awkward. That's where the comes in. Empty chair next to me. He writes and then takes a picture of the chair. I'm truly not trying to give you a hard time or be weird about this. You can sit next to whoever you want to look at the reflection in your sunglasses. Dot, dot, dot. Andy and Tiffany met Andy walking around with Brock yesterday, but wasn't there with them. Just said, just said hey and sat down. See, here's my problem. You guys have never met. You're meeting on a dating app. And this goes back to the theme of this episode that just became apparent. Understanding the fear that might be happening on the other side. The woman that wrote in the first email didn't really acknowledge how tricky it is for the person on the other side to date someone at work, especially someone who's been there a year and a half, especially someone who's younger and 26. This guy is doing what she did to them, to you. He's not really appreciating. You guys have never met. You met on an app you're going to meet sometime in October. It's distance. And when you say, hey, I'm truly not trying to give you a hard time, but there's someone in the reflection of your sunglasses that I can see. And then he just doesn't even like look to soften that, he goes. Andy and Tiffany met Andy walking around with Brock yesterday, but wasn't there with them. Just said hey and sat down. So you sat down next to someone you met yesterday. Six inches apart with close enough to be in the reflection of your sunglasses. Again, I'm not surprised. I. I'm not saying this is a dangerous person. They're not acknowledging the danger that goes on with meeting a stranger because at that point, listen, if he's a little drunk. He's by the pool. You, you're one of the few people he's texting with from the apps. He lost himself a little bit. That can happen. That can happen with a perfectly nice person who's kind of doing the dating app thing. Would I, would I count on seeing them in October? Someone who does this? No. Do I think they're taking me seriously and thinking that I'm someone that finally they found someone normal on the apps? Maybe in the way you're thinking? I don't think so. My, my money's not going on that. So that's my opinion of guy who doesn't have to make a date with you. That's the thing. When this starts in distance and he has no way of letting you down, you are someone fun to text with. That's the problem with starting on distance is, oh, this is someone that can take up the dead space of my day or so I don't have to think about how lonely I am. And yes, you're being used. Your ability to text him back instead of, it's nice to have a text. It's like a gift. You open it up, you see what's inside. Maybe it's something fun. So she writes back, no, something is off. That's obviously not what is happening in this picture. Something has felt off all day, and now I'm seriously confused. So you thought to other texts it was a little weird? Yeah. I'm with you. I'm gonna go see a friend and get dinner. Maybe we can have a phone date another night. Maybe we can have a phone date on another night. I don't know. This is really fucking with my head right now, to be honest. Yeah, I, I, I think. Here's your. Your biggest problem is you're texting with someone as if you guys have been together three years. You're texting with someone as if you've been together three years and it's been three weeks and you've never met. And that's the problem with these apps is you're texting and calling someone on the same device that you do with your parents and your loved ones. And I do get how that can be confusing. I'm not going to sit here and say that you're stupid or that you were lied to or misled. I, I, I'm just saying it is easy to get carried away. And I think you have, because at this point, you can back away at any time and you're trying to salvage something that doesn't really exist. This Sorry. Was driving home. I'm really confused. This weekend has been such a fl. This weekend has been such a flux with moving things, trying to embrace this change and not drinking. Well, he just said he's had a brew. I'm really sorry this is messing with your head. No intention to. I have crazy anxiety about how you're feeling now. He's letting you know he's anxious about how you're feeling because you're letting him know that you. He's anxious because he's not getting an answer. I. He. He still didn't acknowledge. Yeah, it's weird that there was someone in the reflection of my glasses and I'm at an empty pool and it happens to be, you know, and it's someone I met yesterday. There's no acknowledgment of it to me. And this is the problem. It becomes. And we talked about this on the U UP podcast, the. The Sunk Cost Fallacy. You just want to keep putting. You're putting bad money, good money into bad investment. You're putting good energy into bad investment. And you're thinking, great text banter. I can't find anyone. I'm in this rural area in Oregon, and finally someone's cool and fun to talk to. And it turns out they're cool and fun to talk to a lot of people. Because I think, again, this is my perception of guy in town that, oh, we couldn't work it out. We tried to get together, but we couldn't. We couldn't. We'll have to. In a month now, we'll just text forever and I'll have this fun interaction with you over the phone that kind of fills in the parts of my days where I might feel lonely and have. Feel like I have no one to talk to. I. I think this is why, again, a lot of men, me, I'm one of these men that stay, you know, stays single a little bit longer. I've been texting with less people lately. I've kind of made it a point to. It's hard. It's hard to not fill up that day. And I think this is what this guy's doing again. And I'm giving you him. That's what I think. The most empathetic and my least empathetic. This guy's a piece of shit who's fucking a bunch of people and he's going to have you in town and then you guys are going to have sex and then he's going to disappear the next day. That's more likely than YouTube getting married. That's my opinion. J Train podcast at juma. Com. We'll be back next week. Boom.
Host: Jared Freid
Release Date: September 15, 2025
In this Monday Mailbag episode, Jared Freid dives into two in-depth listener email questions centered around dating, workplace crushes, and online relationships. The central theme across both queries: the tendency to "emotionally run ahead of yourself" in modern dating scenarios, especially when your feelings or expectations aren't grounded in concrete real-life interactions. Jared offers empathetic, honest, and sometimes blunt advice, examining both sides of tricky situations while maintaining his signature comedic and conversational tone.
Listener Question: A 26-year-old woman confesses a "massive crush" on her 47-year-old male coworker and wonders how to let him know she's interested—without making the first move or appearing desperate.
Perception vs. Reality:
Jared immediately spots that the listener has constructed an elaborate internal narrative around a one-sided attraction, despite minimal interaction with her coworker.
"Currently, you have nothing. You have someone being nice to you, and you have an attraction to him. So you're building it up into more than it is." (23:10)
The Age & Office Dynamic:
He highlights why a 47-year-old man in a professional setting might be especially cautious about pursuing a much younger woman at work—pointing out the power dynamics and societal judgments involved.
Fantasy vs. Action:
Jared introduces the concept of "emotional masturbation": getting carried away with internal fantasies about someone instead of focusing on reality.
"You're kind of emotionally masturbating to the idea of older guy who's got all his life all set." (25:46)
Taking (Appropriate) Action:
He advocates for intentional dating outside the workplace:
"I think you got to get away from the people at work. I think that's kind of in your way as far as, like, mentally." (32:00)
Self-Judgment & Dating Timelines:
Jared gently refutes the listener's anxieties about "wasting her 20s" or "having been single too long":
"What's too long? I don't believe in too anything. You've been single and you'd like to make a connection with someone." (32:58)
"You can date anytime." (36:41)
Listener Question: A 46-year-old woman from Bend, Oregon, is messaging with a man she met on a dating app while traveling. Weeks into their texting and before meeting, she spots a woman in the reflection of his sunglasses in a selfie and confronts him. She's unsure if she's overreacting.
Texting Isn’t Dating:
Jared stresses that strong texting or “phone dates” are not a substitute for real, in-person chemistry or commitment.
“Great texting banter is like less good than in-person banter. So it’s something. But it’s not everything. And it’s not to mean that it’s going to be great in person.” (56:35)
Getting Carried Away:
He identifies the listener’s mistake: investing emotions in someone she hasn’t actually met.
“You’re texting with someone as if you guys have been together three years and it’s been three weeks and you’ve never met.” (1:15:54)
Reflections Don’t Lie—But People May Soft-Pedal:
Jared deciphers the texts, noting that the man’s avoidance in addressing the presence of the other woman is a big red flag.
“He still didn’t acknowledge. Yeah, it’s weird that there was someone in the reflection of my glasses… There’s no acknowledgment of it to me.” (1:12:31)
The Sunk Cost Fallacy:
He introduces this classic relationship pitfall, where listeners keep investing energy into someone because of time already spent—even if the situation is going nowhere.
Empathy for Everyone (but Realism Wins): Jared balances empathy for the listener's excitement and disappointment while warning against building castles in the sky:
“You’re putting good energy into bad investment. And you’re thinking, ‘great text banter…’ and it turns out they’re cool and fun to talk to a lot of people.” (1:14:03)
“That’s more likely than you two getting married. That’s my opinion.” (1:17:07)
The "Circle Jerk" Analogy:
In explaining podcast sponsorship, Jared cracks,
“That’s a big old circle jerk. I’m jerking you off with a promo code. They’re jerking me off with some cash. You’re jerking them off with your business.” (12:16)
Emotional Masturbation & Dating Apps:
Jared robustly employs the term brought up on the Betches’ podcast, “emotionally masturbating,” as a way to call out building up elaborate inner stories with little real-world basis.
Audience Empathy:
Jared repeatedly reiterates the importance of empathy for oneself—encouraging listeners to seek therapy or professional help for their ongoing self-worth or dating struggles.
This episode will particularly resonate with anyone caught in a cycle of crushes, premature emotional investment, or self-doubt in dating. Jared’s commentary is honest, compassionate, and laced with relatable humor, making his tough love both digestible and motivating in the often confounding landscape of modern romance.