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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 alive from Delray Beach, Florida. That's right, every Monday is a mailbag Monday, where you, the listener, email me, the comedian, all your questions. It can really be anything. Relationship, family, friendship, just anything on your mind that you want to hear someone me give an honest opinion on. Here's the thing. You could ask for advice from anyone in the world and they're going to do their best. We're all going to do our best. But sometimes you ask a friend, they have to make eye contact with you. They have to take your history and make it a part of their advice. And sometimes that comes off as biased. I am going to give you an unbiased look at your question based on how you wrote it. You may add to my bias. You might write something that makes me go, well, when someone writes that, it means this because you might not even know how you feel until you wrote the email. So send it, send it, send it. J train podcast gmail.com. so many people, they'll be like, I just feel better having written the email. Whether you get back to it or not, we get back to it. J train podcast gmail.com. i have three emails from listeners in front of me. This is every Monday. This is coming out on the 22nd of December. Some of your podcasts that you listen to took a week off. Took this week or next week off. Not your papa. Jt, I'm here with you when you need me most. Right now, during those walks, before you go to bed, when you wake up in the morning, you, your uncle J Train is here for you. Remember that. Cuz some of these podcasts I, they, they did best of this week. They didn't do a new episode. They took it off. And you know what? I'm not going to, I, I, I'm not, you know, listen, this is my opinion. They care less about you than I do. I care about you. I want to be there for you. And, and here's what you can do for me. Share the show, share the podcast with a friend, a cooworker, a brother, a sister, a mama, a papa, anyone who wants to enjoy a daily show, we mailbag Monday, that's just Mondays. Tuesday we rant. Tuesday we get ticked off. Ticked off Tuesday. Wednesday we have a guest chit chat Wednesday, little chit chat. Thursday we look at the Pop culture news. So I'm here for you every day. Oh, Friday. What about Friday? Sign up for the Patreon. Patreon.com Jared Freed. Right now on Patreon, you can watch a video with my parents. We made that extra special for Patreon subscribers only. So if you, if you go to the YouTube you can see all the other stuff from Florida. With my family, we got all this behind the scenes stuff that has really been. People really love it. People, I mean, I, I hate doing. The people love it. I have heard amazing reviews from the audience. The people who watch it enjoy it. As I take a sip of water. Let's do three emails. I got three in front of me. Send yours in. I got two sponsors. Support the sponsors if you're in San Diego or the area around San Diego. I'm doing seven shows for New Year's. Yeah, yeah, yeah, yeah. You just said seven. You just said that to yourself. You went seven. Yeah, because I'm doing two New Year's Eve and then Thursday, Friday, Saturday. So I am moving to San Diego for the New year. Come, come, come. Assemble the group chat. And then I'm in Baltimore. Philly's sold out. Sorry, Philly. We were going to add another show and then I was like, you know what? Why don't I enjoy one good show instead of one good show and another one where, you know, you, oh, you know, we tried and you know, we got a couple hundred people and it wasn't, you know, listen, this is me being, this is new confident Jared saying, listen, you got to get these tickets early. Get the tickets early. New York, I'm looking at you. Toronto, I'm looking at you. These are going to sell out. Boston, it keeps selling. I would get them now. Atlanta, Houston, Dallas, Tampa, these are all places I'm coming in the new year. So J. Jared free.com Jared, my favorite. I live now. This person DM me. And this is an email follow up to their dm. Jared, my favorite. I live in New York City now. Used to be in D.C. where I'd go see you and I'm taking a date to your show tomorrow because I want to go see you. And this is my favorite fifth date with this man. Okay, fifth date. I think fifth date is a great date for a comedy show. I think they saw one of the sets I did was when I was running around New York City. This wasn't necessary. This wasn't my show. My show is in February. That's the one where you buy a ticket that says Jared Freed on The ticket, New York City. There's like these showcase shows. So you can see you'll get a little grab bag of comedians and you and you and your date. And I think it's a fun night because you and your date afterwards can go, I like this one. I like that one. Oh, that one was great. That one was not. Not for me. You know that. That's a fun discussion date. So fifth date comedy show. Love it. So she writes, so I'm taking him out, which to me insinuates that dates one through four, this guy, you know, took out his card. She maybe did the, you know, the pump fake to her purse. And he was a men and he was the gentleman. And to feel like a again, in my opinion, he did the thing I would do dates one through four. And now she's going date five. I got it. And I'm taking you to see my New York. And my New York includes a show where Jared Freed is on the lineup. And I enjoy his comedy and I'm hoping you will too. And let's see if we can connect on this. I love this. Everything about this is great. And you know what the best part is? You're acting on your feelings that that is something that you're not really getting at so far because it's beneath the surface. Here you are saying, I had a great time with him on four dates. Now I want to show him a comedian that I enjoy. So we are going to the comedy show. Boom. Wanted to share my invite and incur. Wanted to share my invite and curious should we stepping up our invites. Now she sends an invite. We can post this maybe on Instagram to show people with the names blocked out, but it's. It is a. Honestly. So to go back, she did DM me this. I thought I was on a show that I didn't know about. That's how good the invitation is. It's beautiful. It looks good. It says, you know, special guest. And then it's her name and his name. And it says, featuring Jared Freed, Lindsay's favorite comedian and others. And it says where and. And it says what? It is a beautiful invitation. And it's so nice that I was like, am I booked somewhere that I had no idea about? Like, I thought I was on like a show somewhere else that was a special event. Not just any humdrum New York City comedy club show. Not to say that every show isn't special to me, but, like, I'm kind of going through these shows. So this invitation is wonderful, beautiful, and so good that me A comedian who gets put on these flyers all the time was like, oh, my God, what. What show do I have tonight? So she writes, wanted to share my invite. And I was curious, should we be stepping up our invites too much? I created an invite. It was canvas. So I didn't spend much. That much time. I did. So I didn't spend that much time designing this. P.S. this is us in 2021. So she shows me a picture of us on stage in 2021. We did some sort of dating app makeover thing. So that's great. Here's what I will say. I think what you did is great. The invite looks great. You're excited to go on a fifth date with this guy. You acted on your feelings. Here's my feedback to you. And this is my feedback to make this email more global. This is something I see from daters, single people. Single people are so afraid of messing up that they think we all have to act as a team, that there's some sort of rule, that there's some sort of tribunal of single people who have done it right that are going to tell them, you sent an invite that shall not be done. You've screwed this up. There's no messing this up. When you do something you feel like doing, this is great. You had a great time with this guy. That. That's the thing when you say, should we be stepping up our invites? No, you did a great thing because you said to this person, I, I like you so much and I'm so excited about you that I'm going to make this invite and make this fifth date that no one else would really care about and show you how much I care about this fifth date, they will receive this. They will see the invite. They will know exactly what page you are on. This is huge. If they come back and go, hey, fifth day was a lot of fun. I'm realizing that you are in a different place than me, and I need to let you know that I'm not even going to get to invite land. Like, if to me, if I got this invite from someone that I wasn't on the same page with, I would maybe need to end it. I would have to say, jared, they are really into you and you're not where they are. So. And. And I'd have to say, jared, can I get there? And then I would have to decide, and I might end it, but that doesn't mean you did the wrong thing. Should we be stepping up our invite game? I actually cringe at that question because that insinuate and then you write, is it too much? There's no too much. You acted on your feelings. I think this is beautiful. You let someone know exactly where you are, and you will have a better relationship for doing that. Now, if you've gone on for. The thing is, when people say it's a mistake. If you had gone on four dates and you aren't like, the. The problem is I can't look at every date. I haven't been seeing every day. If I saw that someone wasn't really being an active participant in this date, in this relationship, and then you were like, is it too much that I send an invite? I'd be like, no, but you're going to get an answer. I hope they end this because the four dates were done with you pulling them along. Now if I went and looked at all the dates and I said, wow, it looks like these two are really getting along, and then you made this invite, I would go, yeah, this invite's going to let them know exactly where you stand and that you're probably not dating anyone else. The thing is, I don't think a lot of men me think of dates as like, 1, 2, 3, 4, 5. I think I think of them as, yeah, we've gone on some dates and we'll see. I think the more excited you are, the more you start counting, which is great. You're admitting to your feelings. I think this is great. I think anytime you say we. As far as dating is concerned, dating is an individual sport. It is singles tennis, it is golf. It is swimming. It is you, you, you. I. It is not. Well, what should us daters do? We're not a team. I'm not with you. I'm not doing it the same way as you. You're not doing it the same way as me. All you can do is act for yourself and honestly protect yourself. I go on fifth. Whenever I go on fifth dates, I send an invite because I want to be so excited that I want to make an invite for them. And I want them to be so excited to know what page I'm on so that their invite. They know where I stand and we all stand. That would be, yes, go for it. If I say I'm fifth dates, you know, I don't really count the dates. And, you know, I would hope that I'm more ahead, but, you know, if I got an invite from someone, I'd have to see where I'm at, that I'm at at the time. That's an honest answer. And for you and I It's very different. 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How about you talk to them about neutrophil? How about you get them and I'm going to give you some free money and listen, I'll tell you right now, my mom takes it, she likes it, she keeps coming back. I'm like her dealer. It's easy to get started. No prescription or doctor visit required. Get the Give the gift of confidence this holiday season with Neutrophil. Whether you're treating yourself or someone on your list. Visibly healthier. Visibly healthier. Thicker hair is the gift that keeps on giving. Right now, Nutrafol is offering J train fans $10 off your first month subscription, plus free shipping. Go to nutrafil.com use promo code feather nutrafol.com promo code feather. I love that. So let's do another email. Jared, 29 I'm 29. I've been with my boyfriend, 31, for just over two and a half years. Things have been mostly great. He's usually the one pushing us toward a more serious future. We currently live in New York City, but up until now we spent the last two Christmases apart with our respective families. Me back in my hometown in New Jersey and him back in his hometown in Boston and only see each other a few days later. This year I suggested we spend Christmas together. I didn't care whose family, I just wanted to be with him. And he completely shut it down, saying he wants to keep our usual separate holidays and that he feels stressed about traveling this year. I think it's hitting me harder than I expected because he's usually the one pushing the relationship forward. And now it feels like I've been rejected. I don't know if I'm overthinking it, but I'd love your thoughts. You are not overthinking it. Um, you are two and a half years in, and it's kind of one of those things of, like, the next stop on the bus is engagement. I don't know. Are you guys. You lived. And you said you lived together two and a half years. You lived together. You said, hey, let's do Christmas together. I don't care where. You made it as easy as humanly possible. On. On him. I think this is a. This is him saying, I stop the bus. Hold up. Slow it down now. Is it over? I'm not saying it's over. I'm just saying there's something we don't know. And it could be. He doesn't know. It could be. There are feelings not being said out loud. I think to me, you did what I. What we have called on the UL podcast. You did something called the Reveal. You revealed, I would like to spend Christmas together. And then he took. He caught that ball and he threw it back. Absolutely not. And now you gotta sit with that absolutely fucking not ball and go, what am I gonna do with this? This is a problem. Because I do think you have a problem. Listen, I'm 40, and I have been this guy. So I'm telling you straight from. I. I know something is off because I have been him. I am him. I was him. I hope not to be him because I feel his stress. My stomach is turning because I know that feeling he has. So this is me telling you, if I could speak honestly and openly with people that have said, hey, let's go. What are we doing for the holidays? What are we. There is a point. And again, this I versus we thing is now a theme on today's podcast. You have to go from I to we to be in a real relationship right now. You have tried to make that transition. He has said no, you need to attack that. That's the conversation. And it's not what's wrong with you? It's not. Do you think I'm not good enough? It's. Hey, this is. These are facts. I, you know, and I. I, again, this isn't my argument. This isn't my discussion to have. So easier said than done. Like, from my angle, this is the easiest thing to tell you in the world. Way harder for you to do but you're going to have to sit him down right now. It's December 15th. And this will come out. I'm. I'm taping this on the 15th. It'll come out the 22nd. So the 22nd, I think, before you go home for the holidays, if you haven't already. I think it's a worthwhile sit down to say, hey, I made. I wanted to see. And he's pushed it along in the past. It doesn't matter. All that is bullshit. Everything he pushes along in the past until it became. Until today. Now things are different now you're trying to push along. What's the deal? So, hey, we have been together two and a half years. We live together. I asked you to do the holidays together this year. You said no. I think that deserves a little bit more of a conversation. That's, that's what I would do if I were you. We can have this conversation today, we can have it tomorrow, but we got to have it before the new year. I can't be three years in not knowing the answers to. And I would even say, what's your, what is your thinking with this? How do you. And again, how what I would say, what were the feelings you had when I asked you to do Christmas together? Do you see us doing Christmas together next year? Do you see this going towards an engagement? Do you see this going towards marriage? Where because again, beware of holidays, birthdays, vacations. These are all little tiny tests for the relationship and they're going to tell you exactly how people feel. It's really easy to say I love you. It's really easy to say, oh my God, I love living together. It's really difficult say, get in the car, let's go to my parents and make this relationship a little bit more solid than it was a day before that. Because if he had said yes to the holidays, no questions it, and he didn't feel comfortable about it, it would have been a lie. He actually is being as honest as he's been with you maybe in the last few months. So you got to have a sit down. And I think it's. I was hurt that we didn't do holidays together. You shut it down. Can you give me some background on what made you shut this down? Difficult. I'm sorry. Because you say you're not overthinking it. You have been rejected. You. And it's like now it feels like I've been rejected. Let's start at the holiday. I. And my, my advice to you in this conversation, keep it to the holidays. You were rejected for the holidays. And then bring it outward. Okay, well, what's next? When do you see Christmas happening together? Have you thought about this? What made you say no to it? I these are tough. I feel for both of you. I've been him because it's a reality check. He's got to go home and go, hey, yeah, we're not doing the holidays together because I'm not ready for marriage. Well, what do you mean? When do you think you'll be ready for marriage? Have you thought about this? He's 31. He's on the doorstep. J train podcast@gmail.com J train podcast.com it's beginning to look a lot like holidays on the house at DraftKings Casino. Celebrate the season with bright lights and big wins on all your favorite casino games. 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Last one Jared Feather Feather I met a guy 8 years ago through a mutual friend who tried to set us up at a party, but I did. But I just started dating someone else at the time so it really wasn't entertaining other options. I Let me read that again. I met a guy eight years ago through a mutual friend who tried to set us up at a party, but I just started dating someone else at the time so really wasn't entertaining other options. We met and I wasn't super into him, but we did remain friendly until we eventually lost touch when the friend group fizzled during COVID After I got a job in his neighborhood two years ago, I started running into him constantly. The coffee shop, art openings A concert, a bookstore, even the city bus. He has had a major glow up since eight years ago. He went from nice guy to hot, buff and well dressed. He's also an artist who works for a youth nonprofit. And I really admire how creative, driven and caring he is. Over the last few run ins, the vibes between us have felt strong. His body language, the way he looks at my lips, it makes me feel like there's something more there. The way he looks at your lips? Like this is. You're writing like Penthouse forums. But a few weeks ago, he posted coupley photos with another woman. I had never seen her and heard him talk about her before in our run ins. That means something. That means he's into you, he's flirting with you, and he doesn't want to ruin that. So he doesn't bring up the girlfriend, which, you know, you don't know how far along that is. But if he's posting on Instagram, they are a real thing. But I ran into them both at an event this weekend. She's pretty sweet. And he introduced her as his girlfriend. Okay, normally this would end my feelings towards a guy, but I am still majorly crushing on him. I don't want to interfere with his happy relationship or get involved in any cheating situation, but I can't shake the feeling there's something between us. Should I let this go or is there a subtle, respectful way to signal interest in case he's not as happy as he looks? Hey, have you been him in this kind of situation before? Always appreciate your honest take. Delusional or intuitive? I don't think you're delusional. I do think you're picking up on the vibe he's putting down. I don't think the vibe of this guy in a relationship is necessarily the vibe of him out of a relationship. Now these things can happen. Right now you are thinking of this in a very movie rom com way. You're thinking of this cleanly. And I think, you know, you're saying because you're the. You're the star of your own movie, so you're going. And listen, all of us in our movie, we're the good guy. We're not. We might be an anti hero, but we are a hero. So in this scenario, the way you are playing it out is delusional. The vibe you're getting is totally. I believe. I think this guy's attracted to you. I think he's flirting with you. I think he left out the fact that he has a girlfriend whenever it was convenient. And then you saw him with a girlfriend. And here's my girlfriend. What else is he gonna say? Hey, here's some chick that I live with. Here's the hot woman that I flirt with when I, I'm not around you. Like, what's he going to say? It's delusional for you to see this as a romantic ending. To see this as the one. To see this person that you're having this vibe with as somehow going to end with you guys holding hands in a grave together. You, you know, the, the idea that you guys. Because the way you're seeing it. Let me, let me give it back to you. Is he's with someone he's happy with, but not as happiest. He and you have this other thing that is way more special than they could ever have. He leaves her for you. You two fall in love, and it is like no love ever known on earth. That is probably not the case. You are some chick he finds hot that it never happened with. You are someone he connects with and is very nice to because he's attracted to you. But he also has his girlfriend at home, so it doesn't matter what happens with you. So he's probably, you know, being a little bit more himself, a little bit more taking more chances because it doesn't matter. He's never going to get turned down by you. So it's less risk to act a little bit more flirty, a little bit. You know, the guys with, in relationships, they, they always say to me, you know, they always talk about what they would do if they were single, except they're not single, except they're in a relationship, except they don't have to deal with going to a bar and having to go up to a group of women and saying, hey, nice to meet you guys. I'm Jared. I want to go date one of you. All of you look beautiful tonight. I'm just here by myself. They don't have to do that. So girlfriend guy gets to be cocky McCock stain and act like a different. So I'm saying the one you're getting isn't necessarily the one you will get. The guy you're interacting with isn't necessarily the guy that you're going to end up maybe dating if this rom com of yours works out. I don't know really what you should do. He will always do the same thing. He will always be nice. He will always be a little flirty. He will always be buff and, and, and, and charming. Now what does that mean for you two? I don't know, I, I think to you, I think this is one of those things that you forget it like you just keep doing you, you see him, you're nice. It's someone that's good looking. You know, there's a lot of good looking people that are in relationships that you're never going to be with. So I don't think for you to say, you know, for you to say, should I let this go? Is there a subtle respectful way to signal interest? No, no, no, no, no. Because you signal interest. He either ends things and tries to pursue you. That's not going to happen. You're not going to get this the way you want is my point is you're most likely 99%. I'm 99% sure you're not going to get. Because this happens with dating all the time. I, I deal with this with women that, you know, message me. They want me to take them out for drinks and say, oh my God, you and I should go on a date. And I now I don't end up doing that. And then they, and then it kind of like ruins things I guess. You know, this might shake you out of liking him is to make a move on him with a girlfriend. But you even said you don't want to do that. You don't want to be that person that's getting in the way of a relationship. I think he is going, he is towing the line of flirtation until that point where he goes, ah, I'll back away. I got a girlfriend. So I'm just saying you are more work than maybe he is up for. I don't think so. Delusional or intuitive. You're delusional for thinking that this guy and you are going to be the greatest love that's ever been known. Because that's the only way that this works out where you're happy with it. You're intuitive because yeah, this guy wants to bang you and probably would if it if all else were, you know, if, if the girlfriend went away and you guys were to meet. That's the thing. You only know that he would hook up. You don't know anything else. And the reason he's so nice to you is because he has all these other things that you know, the, all these other things going on. The girlfriend. He doesn't, he's never asked you us, he's never had a chance to disappoint you is my point. So that's why you're looking at him in the, through these rose colored glasses. I, I think you either stay away, or you just kind of keep saying hi and being sweet and nice and, you know, maybe they end and he comes after you. You know, the most likely scenario is they end and he doesn't even ask you out. He sends a dm, and he's like, hey, I've always thought you were hot. And then you're like, oh, this isn't how I wanted it. Jtrain podcast gmail.com Jtrain podcast gmail.com we are here every Monday with a mailbag. Monday. Share, share, share. Tell a friend if they're going through something that you heard here, and then you want them to get an honest take, send this to them. So back next week. Boom. Merry Christmas.
The JTrain Podcast Summary
Host: Jared Freid
Episode: My Boyfriend Won't Spend Christmas With Me! Help! – MONDAY MAILBAG
Date: December 22, 2025
On this Monday Mailbag episode, comedian Jared Freid offers his trademark honest and comedic advice on listener relationship dilemmas sent in via email. This week, the main themes are navigating the individual versus “we” dynamic in relationships, the courage to act on your feelings, and the tough conversations required as relationships progress—especially around the holidays. The episode covers three detailed listener questions, all revolving around boundaries, vulnerability, and reading intention in dating and relationship contexts.
Scenario:
A listener shares a creative invite she made for her fifth date with a man—taking the initiative to bring him to a comedy show featuring Jared himself—and wonders if putting so much effort into date invites is “too much.”
Jared’s Take:
Advice:
Notable Moment:
“Dating is an individual sport. It’s singles tennis. It is you, you, you.” – Jared (08:15)
Scenario:
A woman has been with her boyfriend for 2.5 years, living together in NYC. Despite an otherwise serious relationship, he refuses to spend Christmas together, insisting they each go to their own respective families as usual. She feels rejected, especially as he’s previously been the one pushing for more seriousness.
Jared’s Take:
Advice:
Notable Quotes:
Scenario:
A woman reconnects with a formerly “nice guy,” now “hot, buff, and well-dressed” artist she’s running into frequently. There’s flirtation, but he posts photos with a new girlfriend and introduces her. The listener wonders whether she’s delusional for feeling a vibe and whether she should subtly signal interest.
Jared’s Take:
Advice:
Notable Quotes:
Jared maintains a supportive but brutally honest approach, weaving humor and personal anecdotes throughout. He values emotional risk-taking and underscores the importance of individual action in dating rather than seeking broader approval.
Useful for listeners looking for tough, empathetic relationship advice—served with a joke and a nudge toward self-respect.