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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 mailbag Monday the listener email me the comedian for some advice. That's the show. If you want to email the show. Jtrain podcast gmail.com jtrain podcast gmail.com All We Want are your questions and we love when they're honest. I say we, me and V, my producer on the show, our producer on the show. We love the emails that are specific, honest and a story always helps. Just send it in. J train podcast gmail.com this is an advice show. We do three emails a show from you, the listeners. We'll get right to it. Jared. I'm a guy fresh out of college, 23. I'm so happy to hear that we have young men listening to this show. I, I, I just, you know, when you put this out there, you, you kind of expect the same people every time. Sometimes I don't hear back from putting out the show. This is, this, this feels good to me. So we want more people to listen to the show. I my ask of you for a show that is, you know, this is a mom and pop organization and I just read this article about all these podcasts that are not going anymore. And, and honestly a little bit of that is on you the listener to share. Tell a friend if we talk about something here that connects with the group chat, send the link, don't do the oh well, I listen to this podcast, give it to them. I, I'm begging you to share it as I'm happy we found this new guy fresh out of college, 23, trying to get my life started while I'm still job hunting. I want to date, meet people and actually put myself out there. But I'm realizing how fast dating gets expensive when you don't really have money yet. This, this guy is going to be just fine. This is a level of self awareness that you love to see because he here's the thing, you know, we have wants and needs. You want to be dating. You need human connection. Those, you know, those are kind of different a little bit. If I, and again I read these with you. I, I don't read these before I start. This is a very off the cuff show. I love doing it this way. I love experiencing these emails with you, the listeners. You're getting Them because you want to go on a date. Okay, I got 10 bucks in my pocket. Date's gonna cost more than that. Okay? Instead, that $10 has to go other places to maybe make that human connection that I need again, lots of needs. I feel like I keep going on first dates where I pick up the bill, there's zero connection, and I leave thinking, cool, that was $70 to learn. We have nothing to talk about. I'm not trying to be cheap, but I also can't afford to treat every hinge date like a full night out when I'm still figuring out my own life. I, I love this email because this is a hard thing to admit, and let me gender this for a man. You know, I'm a man. I want to take a girl out, and I want to show her a good time, and I want her to be impressed by me. And this person's admitting, hey, you know, after 70 bucks and then finding out that was the cost to figure out if we connected, you know, like, that's, that's a tough. And then to go, ah, you got to eat it. You got to eat it. Because you can't be the miserable, you know, sack of shit who then sends a Venmo request. Again, like, it is interesting, you know, men are being asked to be better, which I, I, I'm, I'm not against. I, I think the, the, the noise out there, because this guy knows, if he said again, he knows enough. I know enough that if he sends the venmo request for 35 bucks, he's a piece of shit. So he doesn't want to be a piece of shit. He, he is let down by no connection. And the cost that went with finding out there's no connection. Again, this happens from the female side, too. Don't get me wrong. This happens from all sides that pay for the date or have to pay for any date. Even if you split 35 bucks to find out that this guy was a tool. I put on all that makeup that cost me this and that. I did my hair that cost me this and that. I. So again, these costs to everything. We can compare strife. But that gets you nowhere if you want to compare. Because if you're listening right now going, well, I have to pay. You didn't email the show. If you want to complain, email J train podcast gmail.com. what you're hearing is that there is a man with an emotional state on the other side of this dating scenario that, again, doesn't get received. If this guy put this online, put this on TikTok. I don't think he gets like the warm hug of the Internet. I think he gets well, it costs us to do this and you, you owe $70 to learn. We have nothing to talk about. I'm happy he wrote in here. I think this is the place where he is going to be heard and empathize with because I do hear what he's saying. 23, right of college. I just want to. I want to meet a girl who's cool and that we can have some fun together and romp around and maybe she's the one and maybe not. Maybe she's someone that I have memory of and holy. I go on these hinge dates and I got to pay so that I'm so that I don't become a, you know, a big tik tok story where I'm the piece of. And then I realize that's a lot of $70 dates to find this person that's like the perfect one. And again, let me just say I'm a privileged guy. I'm doing okay. I don't necessarily worry about this. I can go on $70 dates every few weeks and feel okay about it. So I hear what he's saying and at 23, I can understand that. So here we go at the same time. I know, let's split. It can kill the vibe instantly. Again, this is a self aware dude and I definitely don't want to come off like some spreadsheet guy on a date. I've never heard that term spreadsheet guy. Basically like saying that like I think from my understanding a spreadsheet guy would be like okay, she didn't, you know, she's just a data point to me which I listen awareness. So I'm wondering if the move is to just start planning dates that are naturally lower pressure and lower cost or if that reads as low effort to. Let me, let me give you some feedback there. I think planning any date is not related to the cost until you get to like a few of them in a row. So first date. Hey, I'd love to get together for coffee. Want to meet me at this nice coffee place that's down the street from. From where you are in your section of town when you make a plan for the first date. I don't think. I think women generally are impressed by a plan being made. You are so far ahead of so many other guys that it's actually like a good thing. I have better advice for you. But I'm just saying I don't think. But I Do think if you do coffee three times in a row they're going to catch on and start going on their fingers. Wait a minute, we don't. He's only spent this much. Is he cheap? Like you become like you know, a detective case of, of cheapness. But I don't think cheap means low effort. I think high effort for cheap dates becomes cheap when it's a bunch of cheap dates in a row. But I, I do think you can keep it low and be fine. So basically how are guys supposed to handle dating when they genuinely want to date but can't keep dropping money on strangers? I know splitting is a turn off, but I'm curious some dates for low cost but fun but I'm curious some idea I know splitting is a turnoff, but I'm curious some ideas for low cost but fun first dates. So I'm going to go in a different direction for him. I could give you a bunch of low cost first dates. Going for a walk and bringing them, you know, a bottle of water and heading towards a place to have ice cream on this walk. You know, ice cream is actually pretty expensive these days. But that's not $70. That's a $30 date at most if you go to a nice ice cream place. So. And again, you might be listening. I, I could ice cream. What is this, Mayberry? Yeah. Most low cost dates are cute and fun and good ways to get to know each other and actually are safer. So I think a lot of people appreciate that that you're not going to, you know, this bar that's got a DJ bumping and it's two in the morning. You know, like that would be not, you know, that would kind of ring to the person that you're like trying for a hookup. Like a lot of low cost dates are not a guy trying to hook up general or they don't come off that way, which I do think is appreciated and not looked down upon and not related to the cheapness of the date. Going for coffee. I, you know, I've gone for many coffee dates that genuinely or that generally doesn't cost a lot. But also it gets received genuinely like a relief. A lot of the women that I had gone out with, and maybe this might be an age thing being that the women I was going out with, 30s and 40s, they were kind of tired of dating and tired of drinking on a Tuesday with someone that they barely had met. Like again, in the same way that you're like, I don't want to waste money on a stranger. I think a lot of women were like, don't want to waste going for drinks with a stranger when I don't like to drink a lot. So coffee, I think a lot of times was a relief for them. So. And again, this is me speaking from how I felt on this side of the aisle. I can only speak for me. And right now I'm doing a lot of speaking for the women. But this is feedback I've gotten over the years of doing this podcast. So like walk, coffee, ice cream. Going to a park, again, you want it to be a very public park. You don't want to be like in the woods. I'm not telling you to go, you know, the national park and go on a forest hike up a mountain. That's not fun or, you know, that's a not fun for me but also a little scary for a young woman, I would assume. Here's, here's the more important part and here's the real advice. What we don't account for on the dating apps is that signing up for a dating app is signing up for expectations. So when you say I'm going on these hinge dates that are costing me $70 a date, it's because you know that when you ask someone out on hinge, there is an expectation that you are going to pay for the date, that you're going to take them out, that you're going to make a plan, that you're going to be what us Jews call a mensch. Here's my advice to you. You are 23, which means you have 23 year old friends that have energy and aren't in relationships as much. You have a bigger swath of people to go out with. I would take that $1. Everyone, everyone has a dollar amount. That's a pie chart. And you know, my pie chart might have a bigger $20 to spend and you might have $5 to spend, but we still have the same pie. I would put bigger slices of those pie of that dollar piece towards hanging out with friends in low pressure, low cost situations. Going to outdoor bars and breweries that have non al options and alcoholic options that are $5 beer night happy hours. I would put the money towards the investment towards going out with friends because that's going to put you around people that you could meet and connect with in. And now you're on the first date with multiple people. Stop zoning in on the one person you meet on hinge and you have to spend $70 just to meet them. Go to a bar with friends where you can move around the bar and meet a few people and you're not locked into one person and then you get to have the bachelor experience. You can go out with 30 women at the bar. And again, I'm not saying he's going to the bar where there's only 30 women for him. This is to women too. Go to the bar with friends and there's 30 men for you and you can walk around and get a little vibe check and that's a better way to meet people. And I know again there's, there's trade offs. You go on the app because you don't want to deal with public failure. So it's really what do you want to pay for? Do you want to pay the $70 is the cost of zero. Public failure. Going out with friends and going to a bar and meeting your friends friends and meeting your, you know, a stranger comes with, maybe they look at you and go, I'm not having a connection like you did. Maybe they say no to like let's go out next Wednesday. Maybe you need to like figure out what your in bar strategy is, which is, hey, this was a really nice I, I think this is a great way to go for a date. This was a really nice conversation. I'd love to take your number. Maybe we can go for a drink sometime. Always compliment. This was a great conversation. It was really nice to meet you. I gotta get going. Can I get your number? I'd love to like make a, make a drink with you sometime. And again, what it is these Going out with friends and meeting someone at the bar is like half a first date and you're getting that with many different people for a fraction of the cost. So I know you wanted cheap first dates for the dates you make over hinge because it's easier to meet people over hinge because you're not as afraid to talk to people on hinge and ask them on a date. If you want your buck to go a longer way, you're going to have to suffer some embarrassment of going out to the bars which again, I want to make sure embarrassment might be too strong a word. It's not that embarrassing. You're 23, going out with friends and having a fun time. Do that and people will be attracted to you. Jtrain podcast gmail.com jtrain podcastmail.com Send in your emails. We've we have two more emails from listeners. How do you pay for this show? Well, you can support the sponsors. We have two awesome sponsors because they can help you rocket money. It's easy to lose track of your spending. Seeing all your finances in one place can help. That's why there's Rocket Money. Rocket Money is a personal finance app that helps find and cancel a unwanted subscriptions, monitors your spending, and helps lower your bills so you can grow your savings. Rocket Money helps you set financial goals and stay on budget by giving you personalized insight on your spending. See all your subscriptions in one place and cancel with just a few clicks. I will say that the person who emailed me right before this ad is the perfect person to sign up for Rocket Money. You're going to have an organized system for your spending and you're going to find out maybe you have some subscriptions that can give you some more money Back to go on dates I use Rocket Money and I love it. I love seeing where I'm saving money and how I'm spending. It's like a it kind of gamifies it for you. 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Coffee with J Train so all those links in the bio of this episode tickets, sponsors and the patriot I, 31, female have been with my boyfriend, 34 male for 10 months and until recently it felt like my first truly healthy relationship. Well, congratulations I guess. I the until recently I'm sorry we we had this is written past tense, a deep connection, shared faith, strong chemistry and talked seriously about a future. Then while I was away, he went out drinking, told another woman he was single, brought her back to his apartment, kissed her, slept in the same bed with her. They didn't have sex. I Mean, honestly, the se. At that point have sex. I mean, I, I mean that, that I not having sex. I guess you could get to the edge and realize the error of your ways. But like, the way you wrote this even brought her back to, you know, there's a lot of mistakes along the way that lead to sex happening, which is the cheating, but this is cheating. But I only found out because I looked through his phone. He never confessed. Yeah, that's also an issue. Since then, he's been crying, taking accountability, starting therapy and saying this was his rock bottom and wake up call. Well, I, I'm not sure you can say it's your rock bottom until you're like, away from it. I think, you know, rock bottom is kind of like a connecting the dots, looking backwards. At least if I look back at my life, I, I, I, I tend to want to personalize these so that, because who am I to tell someone what their rock bottom is? But when I look at like, the parts of my life where I felt more down or sad in the moment, I knew I was sad and not doing the right things. But I also, I can look back now with much more clarity. We're both in thera, we're both in therapy and even trying couples therapy. Well, this is all like, we're doing things, which is a good thing. You're. Do you, you know, relationships take negotiation. This is you two negotiating. So that's good. It's good that you're both at the table. The problem is I still love him. I still feel attached. Part of me thinks maybe this could actually change him. Well, yeah, I mean, listen in Ace, like, I'm not gonna sit here, you know, a friend of yours who is on your side no matter what. And again, like, I'm not your friend. I'm going to act as a friend because you wrote into this show. But that's kind of the power of this show is that I'm not making eye contact with you. I don't have to see how disappointed you get. I hope the best for you, but I don't hate your boyfriend. I don't hate him. I think he made a mistake. So, and it seems like he knows that. So your friend might look at you and go, and, and, and I can understand why it would feel embarrassing that like, your might, your friend might look at you and have their own experiences where, like, they never change, he'll never change. But in the world, in, in the world, on the planet right now, someone has cheated on their spouse in the exact same way that you Were cheated on, got found out in the exact same way that you found out about him cheating. And now they're in a happy, loving relationship in spite of the history of the cheating. Now the percentages of that happening, not great, I would assume I don't know them, but. Because it takes two things. It takes him realizing that he wants to be in a healthy, wonderful relationship with someone that he loves. It takes that which is hard on its own. It also takes you forgiving, not forgetting, but forgiving, realizing that we all have errors that we make throughout life and we all make mistakes and loving him in spite of that. So. And again, like as you take all of those, you know, things that need to come together, the percentages keep going down. Part of me thinks this could actually change him. Yeah, because you love him and you're hopeful that this is the one for you. The other part wonders if I'm just scared to let go. Yeah, I, I, I, I'm sure there's an element of, can I, you know, if I end this, could I find better than this? I don't know, you know, because I don't know your connection. I don't know how you feel. I don't know how you, you guys, I, I don't know if I, any, any, any person could look you and go. Of course you're gonna find better. You're gonna find someone who doesn't cheat on you. I don't know, I don't know if that's true. You might find, you might find someone who doesn't cheat on you, but makes you feel just kinda average in your life and you don't feel special. You don't feel like it's true love, this person. And again, you know what, what gets in the way is some people are like, know, they say, oh, some people are looking for drama because that's the only thing. They confuse drama for passion. I'm not really going to go down that road. I don't know. I, I can understand that you have a connection with him that might not be replicated by someone else. So here are their questions. Is rebuilding trust after a betrayal like this brave or just dumb? It's so interesting that you wrote it that way. I, I, I don't think it's dumb. I don't think it's brave. I, I don't know why it has to be. I don't know why going back with someone after they've cheated has to be that dramatic. You brave soul you fought through to find love together. I, I'm not going to do I. To me, that's a very Internet thing. Or I also don't think it's dumb. I don't think you're an idiot for going back and feeling like this connection is worth salvaging. So let me stick to that question. Is rebuilding trust after a betrayal like this brave or dumb? I. I don't think you need to put the stakes on it. When you say it's br. Is it brave or dumb? To me, you're revealing you're worried about what everyone else thinks. And I would say to you, that's the thing that you have to get over, because everyone's going to say what they want to say and everyone notices, but no one cares. That's the running policy of this podcast. Now, is it dumb if this person makes you feel like you need to check their phone all the time because you don't feel loved and to keep going with it? Yeah, I would say that'd be dumb to keep repeating because you looked at their phone, something was off, you felt something. You felt like you were being let down and you needed to figure out why, so you went on their phone and then you found out shit that you didn't want to find out. So it would be dumb to still live in fear of his phone like I, I and to operate the same way. I think it also would be dumb to be. To say that, you know, I again, we had a deep connection, shared faith, strong chemistry, talked seriously about the future. I think it would be dumb to, to just go back to, oh, look at how good we have all these things and not change how you check in with each other. So now is it brave? I don't think it's brave either. You're, you know, I, I don't. I just don't put that much on it. How do you know if you're forgiving someone or betraying yourself? I. I don't know. I don't. I. That's a question I can't answer. I mean, betraying yourself, are you happy? Do you feel at ease with this person? I. I think that's like a question I, I ask myself a lot in, in, in dating, do I feel totally myself and calm when they're around me? And if I'm with someone who has cheated on me in the past, it would be tough to get to that point again, but I think I could, as long as we were talking and communicating. If you can't get to that point of calmness with them, then I think you're betraying your own comfort. You're betraying what you could have with someone else. Has anyone ever come back stronger from something like this? Yeah, sure. I, I, I don't know what that has to do with you. It seems like you're speaking in right now to me based on this email and the way you asked your questions. It feels like you're kind of rom combing this. You're romanticizing. I think you got to stop romanticizing. I think you need to, like, get to the nuts and bolts if you want to get back with this person. I mean, obviously the couples therapy will work and that will get to you to real conversations. Like, to me, I know I can be delusional thinking that this could be the kick in the ass he needs, but part of me is also not sure if I'm strong enough to let go help a girl out. I, I a lot of this is me telling you how to feel and I can't do that. Here's what I would say. I you sometimes the answers in the email when you write this could be the kick in the ass he needs. And you start the email with first truly healthy relationship. But then you looked at his phone, something was off. Something you didn't feel as right as you're telling me before this cheating happened, the idea that this was all perfect gumdrops and rainbows and then suddenly I need to look at his phone is not true. So I think you need to. And then you're saying, is this the kick in the ass he needs? So to me, you never felt right in this relationship. You never felt at ease. And now the cheating happens. You ended up being right that you shouldn't be at ease. And now you're trying to fix it. To me, I don't think positive change happens in comfortability. If I were you, if I were you, if it were me in this situation, I would look at my significant other. Here's how I would play it. And this is just again, I can't tell you what to do. I'm trying to, I'm putting myself in the shoes of I really like someone. And then they cheat on me. And then they cry to me and say that they're this is the one I would say to them, let's take a month. You do what you need to do. I'm going to do what I need to do. You go to take a month if you want to come back to me in a month or I would have a plan, let's have a plan the calendar for a month from now. I'm not going to Speak to you. I'm going to do my own healing. I'm going to go hang with friends and family and feel the love that I need to feel. I need to refill my cup. That's how I would do it. Because your friends and family, there are no owing, there's no expectation. It's just the most pure form of hang you are looking in a partner you are looking for. I just knocked over the microphone, God damn it. The microphone betrayed me like your boyfriend. Listen, you are looking for a relationship that mirrors the feeling you get of satiate. The satiety of the the fullness you get from friends and family is what you're looking for from a partner. You want that hang that makes you feel really good about the people you surround yourself with. Right now, this person is junk food. They're filling you up, but it's not really nutritious. You're getting filled up with them, but you're not even sure if it's doing good things for your body. It's very confus music. So what I would do is I would say, hey, it is. This comes out April 6th. I would say May 6th. Let's have a meeting, let's have a call, let's have a coffee. I need a month to go hang out with friends and family to see if the hang I have with them feels like the hang I have with you or if that feels different because I'm looking for that. I'm looking for what I get out of my friends and family, which is this no expectation love that comes from them. And then I need you to do whatever you need to do to like, feel right about dating me, get excited about dating me. He might come back after a month and go, you know what? I just wanted someone to love me and you were there for me. And I feel really badly, but like, this relationship obviously didn't live up to what I needed. He might come back and that month meeting and go, you know, that was like helpful for me. I needed to clear my head. This isn't what I'm looking for. I'm not looking for long term right now. I am not ready. You need to go back and find out what your relationships feel like and what is real from this person that you shared 10 months with and had your first, what you thought was a truly healthy relationship. It was not. That's how I would play it. I think all the words you're stuck on are TikTok words or romantic words are things people say to each other. To me, what you're Doing is poetry. And I think you need real action. The real action one month we're gonna like get clean of you and I'm gonna like re acclimate with the things that make me feel good. Jtrain podcast gmail.com jtrain podcastmail.com you know what feels good? A Lola blanket. I have one in my living room right now. Sometimes a sponsor. Like if I told my mom Rocket money sponsors the show, she wouldn't even have a connection to it. Lola blankets made my mom go, oh whoa. I know. Lola blankets. 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That's code Feather. For a limited time, J Train Fans can get 40% off. Select Lola blanket product with code feather at checkout. Just head to l blankets.com use code feather to get 4040 40% off your order after you purchase the last where you heard about them. Support the show and tell them J Train sent you. Wrap yourself in luxury with Lola blankets. That is a deal. We got one more email. Keep sending emails to the show. Jtrain podcast gmail.com J train male listener here. Thank you. Love love when the dudes write in bro time. I have a wedding coming up and I need your advice. I love a wedding advice email. One of my best friends from childhood is getting married and I am his best man. I love it. The issue I have hooked up with the bride. Oh Spaghettio. That's gotta be. They give some context. But one of my best friends from childhood. So best friend from childhood. You could have the. I love trying to guess Based on the way you explain this when you write it. Best friend from childhood. That could be someone that you very. You were very close with. And then suddenly, you know, life comes up. You go to college, they go to college. You hook up with the some chicken. College. You go to another city. He comes to the same city. Oh my God. She moved there too. They get together, they're getting married. Like it could happen. We all grew up in the same area and have some overlapping friends. The bride and I were fuck buddies about 10 years ago. It never got serious and didn't go on for super long. About four years ago, my friend came to me and told me he was interested in her. He basically said, I'm just checking to make sure there's nothing left there. Right? I told him, of course not right now. This is kosher. Right now. We good, dude, Everything's good. Your buddy knows that you guys used to hook up. He even checked with you. You guys cool? And then you gave the go ahead. And now they go off and have their magical romance. 1. One woman's trash is another. I'm trying to figure if I'm saying this right, you're the trash in this scenario. One woman's trash is another. No one. Well, I guess one man's buddy is another. That's the better. That's the way to say it. One man's buddy is another man's sweetheart. That can happen. He basically said, I'm just checking to make sure there's nothing left there. Right. I told him, of course not and go for it. She's a great girl and I genuinely thought they would be a good match. This is very like if you. Again, from his end. He enjoyed her. She was fun. She's great. He finds her attractive. He knew it wasn't her. His match, and I'm. And from her side, she knew that too. Two people again, to go back to the first email needs and wants. We all need human connection. If you're not gonna want to get married, where do you get the human connection from? From another person you're attracted to. So this is all cool. She's a great girl and I genuinely thought they would be a good match. I had also met my current partner by this point and we have been together for seven years now. Even though this was all settled long ago, I can't help feeling a bit awkward about the upcoming weekend. I can understand that. Because you're the best man. Since I am the best man, I will be giving a speech. That's the problem. All of this is Cool. Except now he has to get up in front of a group of people who all know he has hooked up with the bride. Again, not everyone at the wedding knows. I would say the friends know. I don't think grandma is going to be sitting there during this guy's speech being like, you know, she used to suck his. You know, like, I don't think that's happening. Since I'm the best man, I'll be giving the speech. Some of our other friends have been joking about how I should mention having bang the bride. Yeah, I don't think you should do that at all. I do understand why it's on your mind. I do understand why it would be on half of the people who are at the wedding's mind. Also, I do understand that if you're giving the speech and you see one guy do a little elbow to the person next to them, you are going to assume they're going, you know, the bride used to blow him. You know, I understand all of this. Again, if this, if this episode got out, everyone at the wedding would listen to this and understand your, your, your problem right now. But I don't think you're going to do that. I don't think you're going to share this with the group chat, which I wouldn't if I were you. Again, I want this episode shared, but I. Not. Not at your. Not. I don't want to make it your problem. You should, you should not share this episode. We should all just have fun with it and maybe you share it later. Okay. Some of our other friends have been making jokes about how I should have mentioned it, how I should mention I have having bang the bride. I would never do this. And although the jokes are a bit annoying, I'm brushing it off. Yeah, I would be annoyed if I were you because it's really easy to be like, oh, so you're gonna mention how you the bride, and it's really hard for you to be classy responding to that. It makes you less classy when someone jokes about it to you and you have no control over that. That would annoy me. I don't like when people bring me into their immaturity and that happens now you're holding hands with the guy who makes that joke and you don't want to make it, but it's going to be made whether you like it or not. However, this email is great. My girlfriend can get a bit jealous and isn't loving that my sexual past keeps getting brought up. There's nothing you can do about that. I, I mean, you must be a nervous wreck. This whole wedding is all just, it's all, you know, landmines. You are. I would be so anxious if I were you. Just every conversation has the chance to not only make it uncomfortable with you and your good friend, but also make it uncomfortable with you and the bride, but also make it uncomfortable with you and your girlfriend, but also make it uncomfortable with any family member of his that doesn't know about it. And everyone else thinks everyone knows about it. So someone, Come on. Oh my God. I, I, I can't imagine how you're feeling. I feel for you. My girlfriend can get a bit jealous and isn't loving that my sexual past keeps getting brought up. I, I, she feels uncomfortable about attending the wedding of a woman I've slept with. That's not fair. We all have a past and you did nothing wrong. And it's your good friend. And that I'll be so involved in the day. What are they supposed to do? And this is kind of the problem with, you know, this is very male. You know, the idea of we hooked up. It was cool. No, no biggie. Oh, my friend. They actually have a real connection and I'm really happy for them. It's. I don't know if I want to gender it, but it's just you guys are in a very special situation that some, to some people, people, general people, they can't imagine everyone being cool with this. Some people are so insecure that they can't imagine that this would ever happen for anyone. Some people and their insecurity is with their own hookups that they're thinking back to someone who ended things with them that that person considered a buddy. And they didn't consider a buddy at all. They saw a future with. And they're saying if I was at this wedding, I would be angry even though I agreed to this whole buddy thing. So I, I get, so I get this is hard. But the groom is my best friend and was long before the bride ever came into the picture. I'm not sure what my girlfriend expects me to do. I'm with you. I don't either. What can I do to help calm her nerves about the weekend? Trying to be the best man that I can be. I listen, you're in an unwinnable situation. I think you're, you're dealing with everything at once, which is totally normal. And I think you gotta start with a game plan with the girlfriend. I think you and the girlfriend. And again you write. I, I also met my current partner at this point, we have been together for seven years. You're with someone seven years, and you're going to a wedding. I don't know. It doesn't sound it my. You call her your girlfriend. That's the problem. You've been together seven years. It is wedding season. I don't know how old you are, but if you're around 30, let's say you're around. Let's say you're anywhere from 28 to 35. And so is your girlfriend. She's been with you seven years. She's waiting on an engagement. You're going to a wedding, and the girl you used to hook up with is getting married, and she's marrying your again. Honestly, the whole thing, I. You know, it's. Sometimes with these emails, there's a lot to the story, but it really boils down to one thing. And what this boils down to is that your girlfriend is feeling insecure about the relationship because you guys aren't engaged yet, and she's going to a wedding. That now becomes about you and your sexual past where you were being casual. And maybe you still want that. That would be my assumption. If I'm you. You got to have a. You got to sit with your girlfriend and you got to lay it all out. I don't think this is as much about you having hooked up with the bride as it is about you and her and about your relationship and where this is going and how serious you want to make it. And honestly, you might be hearing this and being like, I know I avoid this topic all the time, and I do get weird about our engagement. And, yeah, I. I don't plan on getting engaged to her. And that's the real issue. You might not even have written in about the real issue, which is, you know, you really like your girlfriend, and now you're seven years in and you don't want to get engaged. And you're realizing that right now. I don't know. Because the other stuff, you're the best man at the wedding of a guy who asked you if he can ask out a girl you used to bang, and now they're getting married. Everyone in the wedding is on the same page. Your best friend, your friend from college, he wouldn't have made you the best man. He didn't make you the best man and go, oh, my God, he's got to give a speech. And you guys had sex. Like, he knew all of this. So you being the best man and giving a speech, they knew this was coming. They signed up for this they trust you're gonna give a classy and fun best man speech because your friend loves you and his wife respects you and doesn't think you're an immature asshole. So get that shit out of your head. You're good with them. You're going to give a great speech. You're going to have some piece of shit make a comment. Fine. That's not the problem. The problem is you have a girlfriend that you're seven years in with going to a wedding. That's your problem. Nobody, not very few women want to be a seven year girlfriend at a wedding. Just generally, no seven year girlfriend is looking forward to a wedding with her seven year boyfriend. She's dreading it. The questions, when are you two going to get engaged? What's going on with you two? It becomes. The wedding becomes a spotlight on. You two aren't fucking engaged yet. What the hell is the problem? So you got to sit with your girlfriend and zone in on YouTube this extracurricular stuff. The. I bang the, the fiance and it's my best friend. None of that matters. So I would sit with her and have a real conversation. What, what worries you about. I would do a roses and thorns type of conversation. I would sit with her and I would go. Can we write three things down that we're nervous about for this wedding coming up that I'm getting a vibe is making us all feel uncomfortable. Let's write three things and she will write that you bang the. She's gonna write that you banged the. That you used to bang the. The. The bride. You used to bang the bride. You're ha. You're giving a speech about the couple where you've banged the bride. And the third thing is going to be we are not engaged and we've been together seven years. And I would have a conversation and you gotta have a conversation about that. It might be. Honestly, this might be the breakup that happens before the wedding. Honestly. Because I'm getting a vibe from your email. You're avoiding. You're avoiding with me. I'm the only one that's being truthful with you. No one gives a shit that you bang the bride to be. Your girlfriend doesn't even give a shit about that. She cares that she's going in unlocked. So that was a great email. J Train podcast. I need a cigarette after that one. Jtrain podcast. Gmail.com. we will be back next week. Boom.
Episode Title: I’m the Best Man at a Wedding Where I Hooked Up With the Bride - MONDAY MAILBAG
Host: Jared Freid
Date: April 6, 2026
In this Monday Mailbag, Jared Freid dives into three honest and specific listener emails dealing with tricky dating and relationship dilemmas: how to date on a tight post-grad budget, whether to stay after discovering a partner’s infidelity, and the very awkward situation of being the best man at the wedding of a woman you once hooked up with. Jared navigates all these with his trademark candor, humor, and insight—offering empathy, strategic advice, and the occasional memorable one-liner.
Listener Issue:
"I'm 23, just out of college, job hunting, want to date, but dates get expensive. How do I genuinely date when I can't keep dropping money? Should I plan lower-cost dates or will that seem low-effort?"
Jared’s Take:
Notable Quote:
"Stop zoning in on the one person you meet on Hinge and have to spend $70 just to meet them. Go to a bar with friends... and now you're on the first date with multiple people." (16:32)
Listener Issue:
"31F, been with boyfriend 10 months, thought it was my first healthy relationship, but he kissed another woman and slept (no sex) in the same bed. Found out by looking at his phone. He’s taking accountability and starting therapy. Is rebuilding trust after betrayal brave or just dumb? How do I know if I'm forgiving or betraying myself?”
Jared’s Take:
Notable Quotes:
"I don’t think it’s brave or dumb... When you say 'brave or dumb,' you reveal you’re worried about what everyone else thinks.” (30:20)
"Sometimes the answer’s in the email. You start with 'first healthy relationship,' but then you looked at his phone—so you never felt at ease.” (41:45)
Listener Issue:
"Best friend from childhood is getting married; I’m best man. Years ago, I casually hooked up with the bride—everyone knows, including the groom, who checked with me before pursuing her. It’s settled, but friends are making jokes, and my girlfriend (of 7 years) is uncomfortable about my role at the wedding and my sexual past being brought up. How can I handle the weekend and support my girlfriend?"
Jared’s Take:
Notable Quotes:
"Nobody... wants to be a seven-year girlfriend at a wedding. She's dreading it. The wedding becomes a spotlight on: You two aren't fucking engaged yet." (59:30)
"The extracurricular stuff—the hookup, being best man—that's not the issue. The problem is you and her sitting at a wedding seven years in, not engaged." (1:02:00)
On Effort vs. Cost:
"Cheap doesn't mean low effort. High effort for cheap dates becomes cheap when it's a bunch of cheap dates in a row." (14:15)
Romantic Rationalization Caution:
"To me, what you’re doing is poetry. I think you need real action." (45:11)
On Navigating Old Hookup Dynamics:
"He wouldn’t have made you best man if he had a problem. All that matters is whether you, your partner, and he are on the same page.” (1:00:45)
Jared wraps the episode by emphasizing the importance of honest self-reflection and communication in relationships, whether it’s about money, forgiveness, or long-standing relationship inertia. He maintains a supportive, humor-laced tone throughout, ensuring listeners feel their dilemmas are validated but also nudging them towards tough truths.
To Submit Your Own Question:
Email jtrainpodcast@gmail.com
Noteworthy Segments for Quick Reference:
Tone:
Empathetic, candid, and comic; Jared balances real advice with levity, validating listener vulnerability while also delivering practical, sometimes hard-hitting truth.