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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. Hi. From Richmond, Virginia. Almost forgot where I was for a second. That's right, every Monday is a mail bag. Monday. Me, the comedian gives you the listener advice. Like, that's a little strong the way I just said it. I'm not giving you advice. I'm giving perspective. You write your emails in. What would you write about? Dating, relationships, family issues, friend issues. Anything that's on your mind that you want an honest opinion of because this is the reality. I'm sorry to break it to you. Nobody in your life is being honest with you. Everyone's softening, everyone's using what they know about you to give you the advice. I only have the email that you wrote. That's the power of this show. So I do want you to send your emails if you've got questions, comments, concerns. J train podcast@gmail.com. that's J train podcastmail.com. i have three advice emails in front of me. I've got two sponsors, which is always great and encouraging for me because that means we have listeners, that means we have people. It's working. This is a, this is a very nice relationship. When it works, I put out a show, you get to put your brain on the shelf, let me take the wheel, you get to go to mush and let me take over your head for the time you need to get away from your own thoughts. And then sponsors come in and if they can help you, you use their promo code and then they help this show stay afloat. That's the whole thing. So. And listen, if you have no use for the sponsors, that's okay to share the show. Like the Instagram account, send an email. There's, there's all these non currency ways to help the show. And here's a great way to like help everything. I'm sitting here in Richmond, Virginia. I am going to talk about this on Coffee with J Train, which is probably out already on Patreon. I just love being at a comedy club in a mall. I feel so good right now. I'm so happy to be working on material and people after the show, they go, I'm sorry you have to be here in Richmond. I am so damn happy to go to a first watch and have a breakfast and then come back here and tape a podcast and then roam around this mall. And try to make my jokes better. That. I mean, that's what makes me happy, which is like, how do I. You know? And. And that's why this show. This show makes me happy in a way. But it all leads to that. For me, having a coffee and a weird square that looks like it's from a Hallmark movie. You have the mall near you. This. This mall that I'm in, in Richmond, exists in Alpharetta. It exists in, you know, Dedham, Massachusetts. It. It exists in, you know, the Grove in la. It's all over the country. Some of that is good. Some of that might depress you. It can be both. So I want you to come to the show and make my dreams come true. That's a weird way to put it, but yeah, that's what you're doing. I'm coming to Milwaukee, Minneapolis and Chicago. I heard Milwaukee, we're having trouble. I heard Minneapolis is okay. Chicago is better than okay. I think it's going to sell out. Durham, Charlotte for Lauderdale. I heard Durham is. Is an issue. So we need some Durham activity. I heard Fort Lauderdale having some problems, so we need some help there. Miami. I added Miami because everyone in Fort Lauderdale, if I'm honest, I probably should have added, like, Boca and Miami. I don't know. I don't know. I. Miami and Fort Lauderdale. That's Thanksgiving weekend. Detroit, Columbus, Orlando, San Diego, Philly. That takes us to the end of the year. I added Tempe, Arizona. So all those people that asked for Phoenix. I've done Phoenix so many times. And it's. It's been okay. It's been fun. I mean, the show's been fun. I'm saying ticket sales have been okay. You know, everyone's always like, go to Tempe. I'm like, I've been wanting to. I heard the club there is awesome. So I asked to go to Tempe instead of Phoenix. So that is my shows coming up. Jared free dot com. Go to the YouTube. We're doing some different stuff on YouTube. I'm taping behind the scenes from the DC show. It might be out already if we turned it around. I don't know. It won't be out. That will be on my YouTube. Sorry to cough. I don't know. This is what happens. I start the show now. It's Monday morning. I'm coughing in your ear. What kind of a. What kind of an orator am I? Orator is a very crossword puzzle word. I'm into crossword puzzles now. All right, let's do the emails. Jared Feather. Feather. I'm a benefit subscriber and I've seen you live a few times. Thank you for bringing the laughs, helping me put my brain on the shelf each week. You're welcome. Thank you for writing in and thank you for being a subscriber, that is. I was thinking about that last night. Like, Man Patreon and the subscriber version of the shows have been, like, life changing for me. It just makes this, this all kind of go. And I really appreciate anyone who's involved with those platforms. It means a lot. Here's my question. I've been in a weekly Spanish class for about a year and a half. That is one of those things that I would never do, but I think it's awesome. You ever hear someone do something and you're like, I'm happy you're doing that. Like, you're good for. I wish I would do stuff like that. I wouldn't, I wouldn't. But I think that is really cool. Instead of like doing the phone version, listen, if they start sponsoring the podcast, I'll understand the value of doing, like, you know, whatever the phone version of, you know, Rosetta Stone. But going to a class, maybe meeting some new people with the same interest as you, I'm like, so happy with this. The first few months were a rotating group, but for the past nine months we've had a steady crew of eight people. This is setting up as advice I will give forever on how to meet new people because I think this is great. It's become one of the highlights of my week. We hang out after class in the parking lot, sometimes grab a beer together. This is the dream. I think New York City, you don't need this. It'd be New York City. This is a good way to make a big city small. I think this is great. Over time, it's turned into a little friend group. I'm on a texting basis with a couple of girls. We have a class group chat, but we mostly use that for logit. Logical logistical questions. I read these with you. I never read these before. Just if you're new here, I take the emails. We read them. We go through them as I read them. Okay, so over time it's turned into a little friend group. I'm going to text it here. And here's the thing for, like dating and relationships. This friend group knows 200 people each. That's what they used to tell you with when you saw. I think of dating a lot of times, like selling life insurance. When you sold life insurance, they'd be like, everyone knows 200 people. Same for dating. So it's like, well, are there, like, the most miserable single person will respond to, like, hey, take a Spanish class. You're looking to learn Spanish? Well, I don't think any men are in the class. That's a miserable fuck. No. Meet the people, become friends. And that will be the tentacles that go out and find you someone new. But let's keep going. I'm on a texting basis with a couple of girls. We have a class group chat, but we mostly use that for logical question, logistical questions. I'm an idiot. For the first year, I had a boyfriend who I'd very occasionally mentioned. An espanol. They wrote, I am like. So I like this email. We broke up several months ago. But it's not like I would announce that to the class. You're right. Hey, I don't even know how to start that. Miscomplianos. No, that's like, happy birthday. Okay, amigos. Me, me, boyfriend con me. But, yeah, how would you. You wouldn't tell people. Just people will go, you have a boyfriend. And here's the thing about, like, this group that you met like, a year ago. They'd be like, I think she has a boyfriend. That's how they talk about you. It's not like, oh, she's married and engaged. They wouldn't be that. We broke them several months ago. But it's not like I would announce that to the class. A few months out of the relationship. I think I have a little crush on my small group partner. Here's the dilemma. I'm not sure if you were even. I'm not. Here's the dilemma. I'm not even sure if he remembers I used. Here's the dilemma. I'm not even. I'm sorry, I'm reading badly. Here's the dilemma. I'm not sure if he even remembers I used to have a boyfriend. That doesn't matter, and I don't know how to. Or if I should bring it up that we broke up. I'm not sure that he is single, though. He's never mentioned a girlfriend. You can't be sure. You don't know what he's got going on. If he's never mentioned a girlfriend, that doesn't mean he doesn't have a girlfriend. With men specifically, they say they have a girlfriend, and if they don't, they might have a girlfriend. Just. Just an FYI, men are not very good at outwardly saying unless they're, like, in love. I'm in love. I don't care who knows it. Like, you know, you don't know. But I wouldn't assume he doesn't have a girlfriend because he hasn't mentioned. Plus, I don't want to mess up the good group dynamic if dating would be weird. So any ideas on how to put out some casual feelers without making it awkward? Gracias, Jared. Well, let me just start at it's going to get weird. You have a crush on someone. The group will be fine if the group is worth keeping. So you are a single person who's looking to meet the love of your life. Like that's the stakes, right? That's what we're after. So it's either meet the love of your life or never meet them at all. Never try. Here are the options. Go for it. They become the love of your life. You have kids together, you die while holding hands. And the. The dream. Or you never try and life just kind of goes on. Or you try, it doesn't work out, the group explodes. A group that you know you weren't going to be friends with forever anyways. Or you try, the group take sides and you still have a couple friends from this group and it's different than it used to be. I think of all those options, the worst is not trying. You know, just life goes on. You live in these repeats and you always wonder what could have been. Now I agree with you. There's no need to go to this guy and do a full on. I mean, there's no need to go to this guy and be like, I'm in love. I'm in love. I don't care who hears it. Take me on a date, you cutie piece. You don't have to do that. You could that that's an option. Hey, I've really enjoyed getting to know you over the past year. I don't know your dating situation, but I'd been broken up with the. Well, you don't even have to mention that. I would say, here's the text I would send. Here are the options. You send a text that's like, hey, I really enjoy getting to know you during the Spanish class. I not. I'm not positive of your. I'm not positive your situation. But if you're up for a drink, you have my number. I'd love to get to know each other more. That's. Make a plan and I'm in. That is. And you could even end it with no worries if you've got something going on or this isn't of Interest to you. I'm not looking to shake up the group and make it weird. It was just a thought I had. And that's like, hey, would love to get drinks. That's not you being like, I'm in love with you. I need to have you. That's just, hey, let's get drinks and see if there's like, something different here. Because I kind of caught a vibe. Okay, that's a. That's an option. You're looking for casual feelers without making it awkward. Would that make it awkward, that option? It doesn't have to. It could. Now, let me give you another option. You have friends in this group who are probably closer with you. I would go to a side friend in the group and I would ask, hey, what's so and so's situation? And they're going to go, I don't know. And they're going to have an idea of who they could ask. Oh, I think this guy is closer with him. He would know. And now the game of telephone begins. You have to trust currents. You have to trust inertia. You have to trust gossip. People love gossip. People love other people's problems. People love other people having to deal with the mess that might ensue. That's where you're lucky. None of them are going to wait to make sure. They should talk to their friend about you wanting to fuck the other guy in the group because, oh, my God, I. What if it gets awkward here? They don't care. So they're acting. They're on the tight wire without a net underneath. The way you should probably act in your own life. The way I should probably act in my own life. We should all dance on the tight wire because what's it all for if we don't? But we stay safe? We play it safe. We don't want to shake things up. We're so worried of falling off that tag wire and drop into our death. But that's never going to happen. It's always going to be okay. So that's why the first option of like, hey, send them a text and just let them know, no harm, no foul. Or this route, which is easier but also longer. But you have to trust inertia. So you tell one friend they're going to go to their other friend, hey, what's Jason's deal? And then that person who's closer with Jason is going to go, jason, this chick likes you. And now, honestly, that results in more awkward than you think it's going to. That's the easier route. That will result in more people knowing and inevitably making the group a little different than it was before. So it's, like, weird. It's funny. It's easy route that makes it so everyone knows, or more people know and more chance of awkward. Or the more difficult route that gets you an answer right away that no one else finds out, and you hope that you two adults can be adults about it and not make it weird. But. And that's generally the harder route, which is fun. It's funny. As I talk this out, so. So again, it's. Hey, man, I really think you're cool. I'd love to get a drink sometime. I don't know what your dating situation is. That's. That's the move with anyone that you have. Have a crush on when you say that. This is the move when anyone. If you want to text someone you have a crush on, you want to get a drink. Hey, I'm not sure of what your relationship status is, but I thought we had kind of a cool vibe. I'd love to get a drink sometime, make a plan. And I'm in. So when you say, I don't know your relationship status, you're saying this is under the umbrella of, I'm looking to maybe date you. See what you did? So it's this subtle, languaging thing you stick in something that is so not sexual. Not like, will you please go out with me? You're not holding a flower. I like you. It's not that. It's. Hey, I'm not sure your dating situation, but if you're up for it, I kind of thought we had a cool vibe, would love to get a drink sometime, make a plan. And I'm in. Now, you've been confident, you've been positive, you have let them know what you want, and. And you've put it in a yes or no situation where you can walk away. If you get a no, you go, well, what if they say nothing? That's a no. What if they say, maybe that's a no. What if they say, oh, my schedule this, schedule that? That's a no. Make a plan and I'm in. Plan is yes. Anything else? So those are your two options, or you go to your friend, hey, what's Jason's deal? They go to someone else. Hey, I was just asked by Rebecca what Jason's deal was. I think she likes it. Then that slowly makes its way to Jason where he goes, oh, she wants to fuck me. Of course she does. I'm Jason. I'm Big J. Bo. And Then he either makes a plan or he doesn't. Or in that case, he doesn't make a plan for a long time. I think you're. The more I talk about it, the better option is just go direct to Jason. I gave him the name Jason. Jtrain podcast gmail.com jtrain podcastmail.com that was a fun one. Herobred. I'm really a fan of Herobred. I have it. It's delicious. I make it for breakfast. I make toast with Herobred. And that's the thing about Herobred. They're going to give you the bread that is exactly the same taste as any other bread you'd have, but it has more fiber to keep you fuller, longer. It's lower in calories and it's got like protein. 60% fewer calories than other brands. So if you're like me and you want to eat bread but you want to be more efficient, Hero bread's the answer. And you can put it in the freezer and it stays good for a while. So I'm telling you, I love it. It tastes like any other bread you'd have when you make it with eggs and some turkey bacon. Look at you. You just started the day on a healthy note. If you want a no regret sandwich option, Hero makes bagels with 17 to 19 grams of protein along with sliced bread, tortillas and even croissants. So they have every bread option but better than the bread you're eating. That's it. You'd never know it's low carb and high fiber from the texture. That's a big deal to me and I'm telling you, I eat it. It's good, soft and fluffy, just like you want it to be. Herobred is a huge favor for good reason. Keep an eye out for their delicious small batch drops and get on the wait list for any best sellers. So Herobred is offering 10% off your order. Go to Hero Co. Use code J train at checkout. That's J trainhero co. Every sponsor is in the description of the episode. Jared, big fan of Jay training you up. Thank you. My friends and I send clips all the time and can't wait to see you in New York City. I'm coming to New York. I'm doing a big show. The goal was to add a second show because I did that last time. It's town hall, New York City. It is Valentine's Day or Valentine's Day weekend. Truly, it is a win for any single person. The show is called table for one. And it's about being single and 40. I, you know, if I was to describe the show, it's the show I would have wished I could have done when I made 37 and single. Like, in a world, you know, the thing is I have to put out my work in ink, and you got to move on from it. 37 and single, I was proud of. It's a good special. I think I'm going to put it up somewhere. It got, you know, it's done with its Netflix time and it's going to do live somewhere else at some point. But this is kind of, you know, it's tough because it's like I already talked about dating, but like, it's about my life at 40 and the frustrations of single, but also, like my closeness with my family. It's really turning into do I want to find someone? And weirdly, that's a tough question to answer. All right. I've listened for years and often hear about guys who won't commit because they're quote, unquote, not ready. I mean, I didn't even read this, and I'm talking about this. This person will love the show. But what about the ones who do commit only to cheat from the start? I am sorry. I've known this guy for six years, and after our long situationship, he told me he couldn't be in a relationship due to where he was in life. Okay. Then he started dating someone else, which hurt. But a few months later began texting me again, saying things with his girlfriend were up and down and that he wanted to see me. Hey, I'm sorry this is happening. Why commit to someone just to cheat with the person you once rejected? Well, here's my answer to that. Tough to do. Easier to say than do take. Make it less personal. Consider yourself a situation. You called it a situationship. And then you tried to say, I don't want the situationship. I want this to be real. And he said no. So he said no to the situation you had put up with a certain way it was going for whatever amount of time it was going that way. So when he comes back to you, it is not as personal, even though you know you have to take the good and the bad when it's bad. I'm telling you not to take it so personally when it's good. I also have to tell you not to take it so personally. So the good feeling you got when he came back to you thinking, wow, he must have realized how great I am, it wasn't that it was. He realized how great the situation he had with you was. That is something you can't have forever with anyone. And he's trying to make that happen again. So you're asking for whys. Why risk your whole relationship for someone you wouldn't even date? It's not about that. That you're. You're making it all very personal. And I know that's hard not to do, but it isn't about you. It's about how you and him operated. And right now, he's in a new thing that you're going, well, he committed to her. No, he committed based on the line. They walked. So sometimes you end up in a situationship, and it's like, how do we get here? Oh, we were casual. Because it was casual, and you had good excuses. He might have gotten this new thing, and he had no good excuses. He walked around that walked him into a corner, and the only way to go was to commit. And now he's realizing he can't do that with her, and he comes back to you. I just think this is more about choosing situations than people. So I get the question you're asking. My response to that question is, it's not about you, and you shouldn't go back to this person and you shouldn't text them, and you should dump him and should I tell his girlfriend what's going on? I. I'm always on the side of, like, walk away from the burning house. What's going to happen with his girlfriend? I. I don't think you need to be a part of it. I think if I were you, I would say to him, you're in a relationship. I don't want to be with you. I think you don't even. I think his relationship and all this, like, these other things at play are all excuses and all the reasons. You know, when you guys didn't. You know when he says where he was in life, that was an excuse. He didn't want to make you a responsibility at that moment, and he didn't. So I think what you need to do is dump him. Hey, we're done. I understand you're bringing up his relationship. It has nothing to do with this relationship. This is about you. You and him. Hey, you didn't want to be in a relationship. That hurt me, but that's okay. I'm telling you right now, I don't want to date you. I don't want to be with someone that I'm turned off by this. I'm over it. You have to tell him that because that's why he's coming back to you. Because he is coming back to the situation. He's not coming back to you. He's not even thinking of you too. And, and I, I hate to say it this way, but he's not even thinking of her or you as a people. He's thinking of you and her as options of lifestyles. So you say, why commit to someone just to cheat with the person you once rejected? Is. Is. That's the thing I'd zone in on. They're not committing to them and not you. They got cornered by them in a way they couldn't get out of it, and so they committed. And in your situation, they were never cornered. They always had good excuses. You were part of that. You also were part of allowing that to happen. And I'm sure you allowed that to happen because of the situation. Well, when we first started, I wasn't into him and it was casual for me. And then we tried to do serious and I wasn't even into it. Then I got tired of it. I started to like him. So now when I asked for serious, he wouldn't do it. Like yours offered a lot of ease of situationship hers might not have, and it probably didn't. And then he gets in it and he's trying to find a place he can land after it because he's got to end it with that person. They're not going to make it. And if they do make it, they'll be very unhappy. J train podcast@gmail.com J train podcast@gmail.com Cornbread Hemp. I you know Cornbread Hemp. I use it to get to bed. It's pretty good. Your current CBD isn't hitting like it could be. Make the switch to Cornbread Hemp. Made from just the flour of the plant, this stuff packs a punch and is ready to help fix what ails you. They make THC gummies, THC drinks, CBD oils, capsules and creams, and even CBD for anxious pets who take after their parents. I am using the CBD to get to bed. I love it. It's great. It's helped me. I've been waking up early to go to the gym and it's really been helpful. Whether you're looking to relieve stress or help soothe aches and pains, Cornbread Hemp has what you need right now. J Train fans can save 30, 30% on their first order. Just head to Cornbread Hemp. Just head to Cornbread Hemp dot com J train and use code J train at checkout. That's Cornbread Hemp dot com J train. Use code J train last email. Dearest J Train, we have friends. We have friends having a destination wedding in Mexico. I love a destination wedding issue. They live in the same city as us. So I was excited to potentially have a local wedding for once, especially now that we have a toddler once we learned it was in Mexico. Still excited, but a little concerned how it would work logistically. Now that I've looked up the logistics, this wedding will easily cost us 5,000 for just flights. This wedding will easily cost us. A lot of logistical questions today. This wedding will easily cost us 5,000 just for flights and three nights at an all inclusive hotel. And I thought Mexico was supposed to be cheap. Lol. Can we afford that? Sure. But we also just went on a 10 day incredible European trip for that amount. This would be a not relaxing vacation considering we're bringing a toddler and not planning it ourselves. So we have to add on worrying about car seats, transfers, etc. It feels like they're having guests foot the bill for their wedding. And while I understand money may be tight, I'm annoyed. That's interesting. So it is interesting that I never thought, and you might be right, that people have destination weddings because the destination says get 20. You know, get 40 of your friends to come here. You get the wedding for free. I guess I never thought about that. That was always how spring break worked. I remember when we went to this garbage hotel in Cancun. We went to like, everyone was at one hotel where MTV was. And me and my friends were at this hotel where they had like broken plastic cups. And it was called El Pablito, I think. Is that what it was called? And our one friend Dan, who put it together, we, we. The joke since then, now 20 years later is, yeah, we all went so that Dan could get his free trip. And it is funny to think that's happening with weddings. They said if we're coming and bringing the toddler, he would be a ring bear. Which is adorable, but added pressure to go. Yeah, they need as many people to go. We'll make them a ring bear. Please, please come to our wedding. We need to pay for it. We told them, we told the hotel we'd have 40 people. We're at 39. Please, we'll let you do anything. I've never been to an AI resort before. All inclusive. Okay. AI that could get confusing. I've never been to an AI resort before, so maybe it's actually worth the Cost and worth it. To celebrate our friends. I could just. I just couldn't fathom asking guests to pay this much for a wedding in North America. What do you think? Just grin and ring Barrett. Great. Sign off. Here's your first issue. Here's where your problem lies. You can't do this. I liked your email till the end. I just couldn't fathom asking guests to pay this much for a wedding in North America. Stop it. Stop it, stop it. Don't get on this hot in North America. I couldn't imagine asking guests to pay for a wedding in the northern hemisphere. Stop it. This is destination. You know, it's not like you get to choose the destination. It's their destination to choose. 5,000 in or out? That's it. To me. You go, I. I it it. I guess. What do I think? Is. Can you. Is nor they wanted to have a destination wedding. That's fine. That's the cost. I think it's okay to be like, hey, we are so flattered you invited us. We just can't make the money work right now. We got a toddler. We just took a trip. We wish you the best and send a really good gift because you can afford it. That's. It's that or you go and have a great time. Would you have fun? I think you would. I think you're like, it is funny. You wrote it twice. I thought Mexico was supposed to be cheap. Lol. And listen, jokes all have honesty in them. And how could they make us pay this much for a wedding in North America? What you're saying is this is a trip I would never take and you're turning it into a morality issue a little bit. My point to you is if you go, enjoy, go to Mexico, sit at the beach, have the toddler take a great picture, it's going to be a pain, but not as much as sitting at home with a toddler. You'll enjoy it. The memories will be great. Go have fun. Do you have the ability to say that? Listen, it's great, but the cost right now is not working for us. Absolutely. I think anyone having a destination wedding where it costs 5,000 to go, I think anyone I've ever gone to a destination wedding for has always been like, we can't believe you came. Thank you. Thank you. That's their response, and I think it's the proper response that they're like, oh, my God, we're flattered you even thought they're like, always. They do say thank you to you as if they're in Debt to you. So I do think they acknowledge the money and that they're getting a free wedding and how lucky they are that people want to spend time off from work and their lives to spend it with them. Like, I think destination wedding people do generally understand how to thank their friends and family. You saying that if they chose a better location, maybe you'd go where you think money is worth spending is not a part of this discussion. That has nothing to do with. It's do I want to go to Mexico with my baby and my husband for. And, And I would say all inclusives. I. I think this, I think the all inclusive wedding is fun if you can do it. And if you're sitting there going, I don't know, we're not going to make our mortgage. No, don't go. But I think the idea, what I find most fun about an all inclusive wedding, don't touch your wallet once you get on the property is the, the fun of, like, taking over. You feel, you know what a destination wedding at an all inclusive feels like. It feels like you're on the vacation episode of a sitcom. Like when Zach and the rest of the gang on Saved by the Bell went to Stacy Karosi's beachside hotel. Like, that's what that feels like. Because hilarity ensues. You have the couple that's in a fight. You have the grandparents who are, you know, you know, taking their walker around the facility. It's all fun and games to me. So I think that there's different type of fun that you get with this cost of admission. If you want to do it, where that is, doesn't matter. Like, to me, the destination wedding, where it is is so secondary because where it is is this confined space that could be. It could be San Trope, it could be the Dominican Republic. It could be, you know, it could be Mexico. It doesn't matter. You're at episode vacation at this really bubble experience. So you're signing up, you're paying for the bubble that includes a bunch of characters that you kind of know the backstory for, which is fun. A beach, a buffet. And you talk about transfers, but that's really only the hotel. You don't have to move from there. So when you're asked to pay for the destination winning, it's not, please take this trip to Mexico. It's please take this trip to hilarious episode of a sitcom where you know all the characters. Would you pay for that? Some yes, some no. That's my opinion. J Train podcast back next week. Boom.
Episode Title: Should I Go To My Friend's Destination Wedding?!? - MONDAY MAILBAG
Host: Jared Freid
Released: October 27, 2025
In this Monday Mailbag episode of The JTrain Podcast, comedian Jared Freid answers listener emails covering friendship, relationships, and post-grad dilemmas. The main theme is advice-giving—really, offering perspective—on tricky life situations with Jared’s hallmark humor, candor, and sharp, relatable insights. The highlight comes with a nuanced debate on whether to attend a costly destination wedding in Mexico.
(08:00-23:00) – Email #1: Spanish Class Friend Group & Potential Romance
Listener’s Situation:
Jared’s Advice:
Memorable Quote:
“We should all dance on the tight wire, because—what’s it all for if we don’t?” (18:30, Jared)
(27:30-42:00) – Email #2: Why Do Men Commit, Then Cheat with Their Old Situation?
Listener’s Situation:
Jared’s Perspective:
Notable Advice:
“He's thinking of you and her as options for lifestyles.” (34:18, Jared)
(47:00-1:03:30) – Email #3: Is It Wrong To Skip an Expensive Destination Wedding?
Listener’s Situation:
Jared’s Insightful Breakdown:
Memorable Analogy:
“What a destination wedding feels like: you’re on the vacation episode of a sitcom. Like when Zack and the rest of the gang on Saved By The Bell went to Stacy Kurosi’s beachside hotel!” (1:00:48, Jared)
On meeting people through classes:
“Instead of the phone version... meeting some new people with the same interest as you, I’m like, so happy with this.” – Jared (11:38)
On not letting fear kill opportunity:
“The worst is not trying... life just goes on, you live in these repeats, and you always wonder what could have been.” – Jared (16:10)
On what to text a potential crush:
“Hey, I’m not sure of your relationship status, but I thought we had kind of a cool vibe. Would love to get a drink sometime. Make a plan and I’m in.” – Jared (21:40)
On understanding why people cling to past situationships:
“He’s not even thinking of her or you as people—he’s thinking of you and her as options of lifestyles.” – Jared (34:18)
On destination weddings:
“Go have fun. The memories will be great… but if not, it’s perfectly fine to say it doesn’t work for your family right now.” – Jared (53:55)
Jared maintains a mix of empathy, directness, and humor throughout. He encourages listeners to be bolder in their own lives using gentle but honest logic—never mean, but always real, with plenty of laughter and relatable anecdotes framing every advice point.
If you’re grappling with whether to risk group dynamics for romance, feeling burned by someone holding onto you as a “comfortable backup,” or debating whether an expensive destination wedding is worth it, this episode offers Jared’s signature blend of wisdom, laughs, and practical advice. Key insights: take your shot (if you’re nervous about romance), don’t take other people’s shady relationship behavior so personally, and never feel guilty about declining a wildly expensive invite—just send love and a good gift.
For more, send your dilemmas to jtrainpodcast@gmail.com and join the Monday Mailbag!