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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 J Train Jared Freed coming to you live from New York City. That's right, every Monday is a mail bag Monday. Me the comedian. Take your listener emails and you can send in anything you like. Jtrain podcast gmail.com jtrain podcast gmail.com send in anything you're going through and we'll talk it out. That's the whole power of this show. And if you were at the book talk that I did, which I'm taping this Sunday after finishing the book tour, thank you to anyone who came out. They were really just, like, wonderful. Like, it was great to meet everyone and sign the books and have a conversation with anyone who wanted to and kind of, you know, just, we, we shared a sensibility and, and it was. That's a really special thing. And I think when you write into this show, you're getting someone who's thinking through your problem and acknowledging it's a problem, no matter how much maybe know the world might not think it is. I, I'm. I'm going to talk about anything you send in. J train podcast gmail.com Also, I'm not going to have to make eye contact with you, so I'm going to be more honest than maybe your best friend would be. And from what I've heard, writing out the problem. Sometimes it helps just to do that, to write the email. So send in your. We always need question. We always need advice emails here. I know it's hard. I know it's hard to open up. Send it in. J train podcast gmail.com I mean, it's, it's funny because I posted a video of the Q and A. If you go to YouTube, you can see the Q&A from DC and listen not to. I mean, I could sit here and pat myself on the back. You're listening. But I'm saying, you see in the comment section of the clip I put up on Instagram, and it's just horrific. It's judgmental. It's, you know, if someone's asking, and, and the woman was asking about she's going on dates with a guy and he's worn, you know, sports gear. And I think it's a wonderful question. I think it's like, and, and if you go watch the full version on YouTube, it gets into like, do you like this guy? You know what, what is Your problem, it's not about the, you know, the sports gear. Do you, and are you trying to, you know, make a case for why you can end it with someone who you don't really like and then you get to still complain about dating. Like that's a, generally a lot of these, like they don't wear, you know, something nice for the date. You know, am I, do I have a, you know, a leg to stand on? And again, it's deeper than that. But if you sit there and go, you know, the comments just kind of prove to me that not everyone is built to talk about these things. Not everyone is who thinks that, you know, that gives you an opinion, is really thinking it out and really looking to have fun with you. And that's really what this is all about. I want to have fun with you and your, your problems. So you might feel a little bit better about them. I have three ME emails, then I have one ad. I'm on the road back on the road. Cleveland this weekend, the Hamptons, Miami, Red Bank, New Jersey. Foxwoods. Portland, Maine. I'm also gonna be in at the Paramount on Long Island. Huntington, Huntington, huntington. Yeah. So jaredfruit.com there's going to be more dates being added all the time. Also I have a date for the Netflix special. The Netflix special is happening this fall. It's coming. We, we shut the book door a little bit. I mean you can go buy the book. The book is out there. But it's time to like for me, you know, this promotion train to move on. There's a Netflix special coming and I'm really proud of it. So I'm, I'm so excited for people to see it. I have a date. Um, I'm gonna be asking you guys to, you know, to, to back me up once again and I hope and, and again I, I, I believe in the special. I think it's, it's gonna be worth a watch and worth sharing with friends and family. Especially family. Let's do some emails. Jared, I've been a huge fan of your podcast and stand up for years. I've been going back and forth on this and need your advice. I'm a 27 year old female. My boyfriend of a year and a half is 32. We recently moved in together. He and a plus one have been invited to his childhood friend's wedding in Italy later this year. He says they were best friend. He says they were very best friends from ages 0 to 12. Since then they haven't talked much or even seen each other except for Some texting this year when the friend reached out to my boyfriend for his address for the wedding invite and related details. Okay, so friend from way back when invites you to his. Invites your boyfriend to his wedding in Italy with a plus one. My boyfriend believes it is his duty to go to this wedding because of how close they were during childhood. I don't understand that because if I were invited to the wedding of a childhood friend who I had lost contact with over the years, I would in no way feel obligated to go. We have many weddings and engagement parties to go to during this era of life and my job, first year lawyer makes it difficult for me to take a vacation vacation when I do, especially for a bigger trip. I'd like to have input on when and where it is. However, my boyfriend is so set on going to this due to his feeling of obligation. I feel bad making him go to this wedding across the world alone since we are in a serious relationship and I want to be supportive. He's not pushing me to go because I shared my thoughts about it with him, but I think he would be bummed to have to do it alone. Do you think I should go to the wedding? Is it selfish or fair of me not to? Thanks for all your help. Maybe a selfish girlfriend. Now this is. I, I love this email because I, I think this is like, this is difficult. Let me, let me, let me say right now like I'm sitting here being like. To call you selfish for not going is. That is not something I would call you. I think that's like, that's, that's, that's too. If we're going to take words seriously, which I think we should, calling you selfish is not a helpful thing. I don't believe you would be selfish. I think there's a. I think if you're, if, if I'm to give feedback to this email, I think the judgment of it, and this is my feedback to you is my boyfriend believes it is his duty to go to this wedding because of how close they were during childhood. I don't understand that because if I were invited to the wedding of a childhood friend who I led. Lost contact with over the years, I would in no way feel obligated to go. I think this is one of those gender differences. If I'm to find a space in your email where I kind of was like, not that that I disagree again because I listen, I'm with you. Your first year lawyer, you want your vacations to yourself. You're at the age 27 and he's 32. Those are the ages you're deep in wedding obligation season. I think when it comes to male friendship. I was talking about this with my brother. My brother and I, I stayed at my brother and, and Ruthie at my brother and his wife's place over the weekend for my book tour. And my brother was like, you know, Jared's my friend. And then the rest I'm like, keeping up with when I keep up with and I feel the same way. I'm like, you know, Harry's my friend. And the rest I keep up with, when I keep up with it is way less delineated. It is men, the men, the male friendships I have come in and out, open door policy, no questions asked. And I understand he's saying he has an obligation. I think it's less obligation, it's more. This is a friend, this is a friend from way back when yet. And if put the task of answering, you know, when's the last time you talked to them to give a reason to going, you know, I don't think many men would sound really so like, oh, my God, you have to go. Like, I, I, I actually think it is quite normal to get this invite for him. And so I think when you're putting on it how you relate to your friends, which, generally speaking, women like, I like I, I don't know a lot of men who have had friend breakups. I don't know a lot of men who are like, those are my best friends and those are my, you know, those were my friends, but not anymore because they haven't been there for me. Again, there's pros and cons to this. Male friendships aren't that deep, but they also don't come with this tallying that goes on with a lot of female friendships where who's been there for me, who's in my circle now, who's outside the circle. And I think for him, when he gets invited by a buddy, if you weren't in a serious relationship with him, he wouldn't even like, question, should he or not? Should he or shouldn't he go? I, I don't think, I think you'd be like, oh, that's my old friend. I got to go. And we go way back and he's inviting me because, and again, like the, you know, the text that he hasn't had in years with him, but it's just to find out his address for his wedding in Italy. It's like, weirdly not that weird to me. So, so to come back to the question that you had, which is, am I being selfish? If I decide to opt out, I think it's okay to opt out. I think it's okay to say, hey, let's look. And again, I think a serious relationship isn't about going to every wedding together. It's about negotiating and being a we as opposed to a me. What are we going to do with the 10 weddings we have this summer? Is a very different conversation than what are you going to do about your wedding? This guy isn't even your friend. So that was. That would speak to me, hey, I have, I have been invited to this wedding. What are we going to do? I mean, I can reference my own life. Emily had a friend get married, and then I went to the wedding. Of course, it, it, it fit in. We weren't together when she got invited to it. Then she got invited to another wedding, and the person was like, does. Do you want a plus one? Because I know you're dating Jared now. And she was like, well, let me check in with his calendar and what he's doing. And then we had a discussion. And she's. She knew that I was on the road. And I'm. I mean, when this comes out, I will have flown from New York to la, and then I'll go from LA to Fort Lauderdale. I'll. And then I'll be back in Delray. And then her wedding that I got added on to was, is going to be this coming weekend or the one that just passed when you're listening to this. So I said to her, I was like, she's like, you don't have to come. It's okay. I know it's last second and you got all this stuff going on. And I'm looking at it going, well, I do have all this stuff going on. But also, once, once the stuff is over, it's not that big a deal for me to fly to this wedding and then fly back. Like, at that point, I'm in it. I'm okay with it. But it was a discussion. It was a we. So I think where you. I think where you become less selfish, and I don't think you're being selfish. I think where it becomes a discussion, I think a judgment of why he feels the need to go to this wedding is, Is a different thing that I would. I would say isn't right to do to him. If he feels he has to go, he has to go. That's what's going to make him feel good. If you would do differently in your life, that that's not really part of this. And again, that might relate to female friendships and male friendships. Now if I were you and I would say, hey, we got. Here are the weddings we got this summer. Let's put em all on a sheet of paper. Uh, we're gonna go to this, this and that. We have a budget of this, this and that and the Italy one. I just, I can't get to it. Can we figure out the Italy one? I think that's a better. I don't know what the answer is for you too, because I can't say that to you. I do think the angle is a better pursuit than the one you're taking. J train podcast@gmail.com J train podcast mail.com we have one sponsor, Nutrafol. When you're feeling good about your hair, you feel good about everything. Neutrophil is the number one dermatologist recommended hair growth supplement brand. And it's the number one hair growth supplement brand personally used by dermatologist. Neutral. Neutral hair growth supplements are peer reviewed, NSF certified for sport and clinically tested. It's not a one size fits all approach. Neutral offers multiple formulas for men and women tailored to different stages of life and lifestyle factors. They make it easy to go get to get support that's right for you. I will say this. My mom has told me she loves that her hair feels fuller and thicker. She keeps coming back, which is like the best recommendation of them all. And if I'm out there dealing with hair insecurities, there's a list of things you can do. I think Nutrafol is the first thing on the list. If you haven't tried Nutrafol, that is. I think that's number one stop. So let your hair become one less thing taking up space in your head. See thicker, stronger, faster growing hair with less shedding in just three to six months with Neutral for a limited time, Neutrophil is offering J train fans $10 off your first month subscription plus free shipping. When you visit neutrophil.com enter promo code feather that's nutriful.com spelled n u t r a f o l dot com promo code feather. That's our 1 sponsor. Many ways to support the show, Use the promo codes. Sign up for Patreon, where I do Coffee with J Train. I talked about getting brought as a guest to a wedding on Coffee with J. I'll probably talk a little bit more about that. I forgot a whole story from that. So if you're listening now, there's a new coffee with J Train that I haven't taped yet that will include a little bit more wedding commentary. Jared, would love to hear your thoughts on matchmakers. I feel like they are all the rage on the Internet these days, so I ended up getting one. I was insane. It was insanely expensive for a six month contract and they haven't introduced me to any man I couldn't have met on a dating app. I have only been on second date out of the first six dates and the last guy literally didn't show up to the date. Do you think match making is something I should continue to pursue? What should I try if I have been hating dating apps and matchmaking? Isn't it? I love this question. This. We have a. We we basically we. A couple of these questions were reusing from the Q and as that I did during the book talk. This was one of them. I first want to say matchmaking is a. I think matchmaking. Matchmaker Maria is a friend of mine. I'll be up front. I'm biased towards Matchmaker Maria but I also went through the process with her and there is value in the profession. If it's a question of is a matchmaker a valuable profession? Yes, that's my answer to that. Is it for everybody? No. Like most things, most things are not for everybody. There's a specific candidate for matchmaking that I think would be wonderful. I think matchmaking as if I was a woman, put my name into their database. I think that's a no brainer. Have a matchmaker, have access to you in some way or some form where they could call you up and say hey, you came up in my database as someone who would be a prospect for someone I'm dealing with. I, I think that is something that if you're single and it's kind of like putting your, your number into the. Into the jar for who? You know, putting your business card into the jar and seeing what happens. I think that's like putting a message in a bottle and letting. Letting fate take it, you know, take its course. So matchmaker Maria I know has a database. When I did there was a, there was a time where on you up we, we got the. The. The. Not the mystic but it was another. We went to like a TikTok, you know, crystal woman who was drawing pictures. You could pay her to draw a picture of a, of the woman you'd fall in love with. And we did it. Matchmaker Maria saw the woman that the in the picture and found a group of women that fit the description for me. So that's how great their databases are. Where if I'm a woman out there who's single and matchmaker Maria is looking for people for her database, I would say submit. Why not? I, I, I. And you're in the care of a woman who understands safety and giving affirmation. They're very, the matchmakers are very serious about information stuff. Giving out information and, and setting you up on dates that are supposed to be a win. Again, a good matchmaker will do that. Not to say there aren't ones that I wouldn't hire. I'm going with my experience. Here's the other thing I would say about a matchmaker. A couple things about your email. It was insanely expensive for a six month contract. If you know the idea of expensive and not expensive is up to the beholder. My dad always said how much is it? You know, if I said how much does it cost? My dad would always say however much people will pay for it. So the it was insanely expensive for a six month contract. I have no doubt that you feel it was expensive. That's okay. I think when you say and they haven't introduced me to any man I couldn't have met on a dating app, I think you're setting up an unfair bar for a matchmaker. I think you're coming into it with bad faith when you say that it's any man I couldn't have met on a dating app. In what world is is the man you couldn't have met on a dating app? Who's to know what that is to you? By what standards Is it because you didn't get married to the guy that she set you up with and when you met him, he was like, what's a dating app? You're dealing, you're living in a world where all men know what dating apps are and have probably given them a shot. Now you could meet someone and they go, I have never been on a dating app and I never would. But I'm only doing this fine. But I, I, I don't, I, I just think it's an unfair view of the matchmaking service. If I were to sign up for a matchmaker it would be because I want something very specific and I would have to be okay with sounding morally bad. And that's the beauty of a matchmaker is that they don't come with judgment. If I you want a certain height, a certain type, a certain background, a certain amount of money they're making. All of these things are things you can discuss with a matchmaker and they will, they will be. They will give you honest feedback. I don't have that guy. I or I will keep an eye out for that man or woman or whoever it may be. But I think the more specific and if you're. I think this also has to do with time. If you don't have the time or you don't want to put the time into going on dates, you know, with via dating app. I think that's when you go to. I think you have to be out of time. Not I hate them. I don't think that's enough. I don't like the dating apps. I, I don't think that's enough to get you into the matchmaker game. I think I don't have time and this is not where I want my efforts to. I think that's, I think again, if you're specific about what you're looking for and time is of is. Is valued differently for you, I think a matchmaker is a great option. Now you say should I continue to pursue. I think you've given up on it. I don't think you're. If you're saying all these people are I could have met on a dating app, then you don't see the value. I would stop doing it. And you say you don't want to do the dating apps. I would say you go hang out with friends and family. Again, that's. Again, none of these answers are easy. None of them are. If there was an easy answer, everyone would do it. Hang out with friends and family. Go do the walk thing that I've been talking about. Go on 12 walks with 12 different couples. Let them know you're single and have fun with these people so that they know you're a fun person that they should be on the lookout for. That would be my suggestion. But other than that, you know, I'm not going to tell you to go into a grocery store and start looking around and asking dumb question of guys. I think that's advice. Jtrain podcast gmail.com J train podcast gmail.com Want to thank you guys for being a part of this podcast. We got one more email. Thank you, thank you, thank you. I got great episodes. You know, this has just been fun to do. So thank you, thank you, thank you. Last one, Jared J. Train, repeat offender here. I wrote to you about my long distance situationship and how I basically wished him luck and ran away after asking if he wanted something more. I remember that that was pretty recent. So you're back. First I shared that pod with Everyone and we had the laugh of our lives at my expense. Lol. Well, I hope you know I didn't try to make fun of you. I did try to help, but laughing at myself is how I get through the hard times. So honestly, it was perfect. I learned a lot. And then looking back, I definitely didn't handle it well. Well, handle it well. Well, it's been six months and I'm going to be in town. In town. Well, it's been six months and I'm going to be in his town for work. I finally realized that it was never that serious and I got a little carried away emotionally masturbating the fantasy of it all during brunch with my girlfriends. But my question is, is fun and good company still allowed? Because I'll be in his city next week. Can I reach out when I'm in town? If so, what's the best way to do it? I tell myself often that Jared and his girlfriend are the exception, not the rule. Lol. If I would say no. If you're even referencing me and my girlfriend who were broken up and then got back together and you're doing this six months after when it was long distance, I don't think you can handle it. That'd be my feedback to that. I know you're being light and you know, writing to me, it doesn't sound like you can handle it if that's even an option. In your mind you've talked on you up about thinking of her but never quite bringing yourself to reach out. Then one time you were in town, she reached out and the rest is history. Again, you're referencing my story. I I, I'm, I'm not going to tell you it can't happen, but I'm not going to tell you chances are likely. Sorry if I'm getting any of the details wrong. So now I'm wondering would I look crazy reaching out, I think, or is this a normal thing people do once they've accepted someone isn't the one? And if reaching out is fair game, what does that text look like? Something flirty, friendly and low pressure. I don't want to sound like I'm proposing marriage, but I also don't want to sound like I'm emailing customer service. Or do I avoid completely because I may look maniacal at this point? Lol. Signed looking for vibes, not vows. You are mixing the two. I will say this, you start with but my question is, is fun and good company still allowed? That is different than everything you went on to explain. You Say, is fun and good company allowed? And hey, Jared, you and your girlfriend who you just invited to move in with you in Florida and make a move and, and take a chance, and, and you're together in a serious relationship with, you know, you did it that way. It's like, well, that's not fun and good company. I think you have to assess that. And, and I do think six months is different than two and a half years. You know, I'm not going to serve up. I mean, the worst advice in the world is here's what happened to me. I think that's like the worst basis of, like, I think you can say, here's what happened to me and here's how I felt. So here's how I felt when I received a text from my now girlfriend. It was just to get coffee and catch up. It wasn't this plea to, like, get back together. It was, let's talk. I think if you and I, and I'm not remembering all the details of your first email to me, but if there wasn't like an ending to that, you know, also that's just like hanging out there. So that's different than my experience, which was there was a breakup and there was, when there's a breakup, there was a significant, you know, for me on my end, the reason I, you know, had thought about her and didn't reach out is there was a breakup and going back would be, you know, it would be, in my opinion, you know, messing with someone. And if I wasn't completely sure, that's why I held back. So, and I get, and I remember your situation being this, you know, we're hooking up when we're in town and, and maybe it's not more, but he, you know, you're assuming how he looks at you and how he feels about you. I think that's a little different. Not to make mine better or worse. I'm just saying the vibe feels different to me. On, on what you're asking about. If there wasn't a breakup and it wasn't, hey there, I think a breakup is respectful, and then that breakup is to be respected. If there was no breakup, then there was no real respect for what was going on. And then, you know, so will there be respect for the new. Yeah, I don't know. I, I, I think to me, and this is purely not based on the situation, like, if this was asked to me, hey, should I go back and message someone that I dated six months ago? I would be like, yeah, but keep, you know, keep your wits about you. Like don't, don't get carried away. Know what you want. I would again, I would suggest reading the book. I mean like not to be, not to like pimp my own. But the book for me was a lot of like the beginning of the book and assessing what type of single you are, what type of alone you are, what type of afraid you are. All of those things are, are important to assess because right now you're not. I, I would say it's less about him, it's more about you. You're not really self assessing based on your email. Oh, I'm just like, is it, is fun and good company still allowed? And then you go on to explain that you're looking for a boyfriend. You're not looking for fun and good company, so you don't even know what you want. So my biggest advice is don't go asking other people to tell you what you want. If he likes me, then I like him. Is not a great way to go through life. That's my thought. Jtrain podcast gmail.com Jtrain podcast gmail.com we're here every Monday with a mailbag. Monday. Love doing this show. Thank you for listening back next week. Boom.
Host: Jared Freid
Date: June 22, 2026
In this episode of The JTrain Podcast, comedian Jared Freid tackles a fresh batch of listener queries for Mailbag Monday. The central theme revolves around navigating modern dating dilemmas—with a special focus on whether matchmakers are worth the investment, handling tricky wedding invitations, and reconnecting with old flames. Jared brings his signature warmth and humor, providing honest and sometimes tough love advice, all while sharing his candid thoughts about relationship dynamics, gender differences, and the pitfalls of relying too closely on personal anecdotes in dating.
(Listener Email at 06:40)
A listener writes in: She's a 27-year-old first-year lawyer and just moved in with her boyfriend, 32, who's invited (with a plus-one) to a childhood friend's wedding in Italy. The twist: the boyfriend and the groom were close from ages 0-12 but have barely kept in touch since. She struggles with seeing the point of going, given her workload and packed wedding season. Is she "selfish" for not wanting to attend?
Key Points:
(Listener Email at 28:50)
A listener tried a costly matchmaking service for six months, but found it disappointing—no better dates than from apps, and a few outright no-shows. Is it worth continuing? Are there better strategies beyond apps and expensive matchmakers?
Key Points:
(Listener Email at 54:10)
A self-described “repeat offender” wrote in months ago about a long-distance situationship that fizzled. She’s visiting his city for work; is it okay to reach out? Is ‘fun and good company’ a real option, or is reopening the past just asking for trouble?
Key Points:
On what makes a relationship work:
“A serious relationship isn’t about going to every wedding together. It’s about negotiating and being a we, as opposed to a me.” (22:05)
On gender and friendships:
“Male friendships aren’t that deep, but they also don’t come with this tallying that goes on with a lot of female friendships…” (16:00)
On using a matchmaker:
“That’s the beauty of a matchmaker—they don’t come with judgment. If you want a certain height, a certain type, a certain background…all of these things are things you can discuss with a matchmaker, and they’ll give you honest feedback.” (36:45)
On why dating is tough:
“If there was an easy answer, everyone would do it.” (41:59)
On self-awareness and reaching out to ex-flings:
“Don’t go asking other people to tell you what you want. If he likes me, then I like him, is not a great way to go through life.” (01:03:30)
Jared’s approach centers on self-awareness, open communication, and realistic expectations.
The episode’s tone is candid, direct, and self-reflective, laced with the humor and tough love listeners expect from Jared. If you want pragmatic, no-frills advice for life’s modern dating messes, this episode delivers.
Timestamps of Key Segments:
For more info or to submit your own questions, email jtrainpodcast@gmail.com