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It's a mailbag Monday. 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. I'm from Delray Beach, Florida. That's right, every Monday is a mail bag Monday, where you, the listener, email me, the comedian with your questions, anything you'd like, anything you want. Any question you have that you want to hear someone just air out. That's the whole point of this podcast, to give you relief. Relief from the everyday struggles of your life, the everyday stresses. I have them too. But this podcast is to be able to put your brain on the shelf. And if you do, email in for someone else to chew on the bone of your issue. We like specific, we like stories. We like friend debates, family problems, relationships, dating. And if you're a fan of the perspective given here, you're going to love the book Walking Red flag. It is out. It's there. You can order it, you can listen to the audio version, send your emails. We've gotten more emails since the book tour because I think, you know, the more you put out of this type of content, the more people trust it, which is a true compliment. Thank you, J train podcast, gmail.com. let's start. We have three emails from listeners. Jared, huge fan of you up and the daily J Train episodes. My mailbag Monday is I'm a female, 28, trying to navigate my relationship with my fiance's sister. 23. 28, 23 female. Two different humans, that's okay. Not different doesn't mean bad. 23 year old woman is gonna 23 year old woman. 28 year old woman, gonna 28 year old woman. Generally, again, I'm living in generalities, but like, there are things that would surprise me from a 23 year old woman and there were things that would surprise me of a 28 year old woman. Same with you. Oh, I own my home and I have a great job that I love. You'd be like, and I'm 23. You'd be like, what? How? What? Good for you. Surprised I wasn't there at that age. All of those things are true. So I mean, 23 year old man, I want to get married, I want to settle down. I'd be like, what? Where are you from? They'd be like, the big city. I live in New York. I want to settle down at 23. I'd be like, who are you really? You ready? You must have confidence up the wazoo you must be delusional too. Confidence is a form of delusion to me. So again, like these things do matter. And if you're writing in as a 28 year old female trying to navigate your relationship with a 28 or 23 year old fiance sister. There's a lot in that sentence. I, it is two different age groups, two different mindsets. Also it's your fiance's sister. You, you need, you need this relationship to be okay. It, it serves your life. There is per, you know it. We, let's not overlook 28 year old female trying to navigate my relationship with my fiance's 20, 23 year old sister. She is personally motivated. How do I make my life easy thanks to this woman I have to deal with for the rest of my life. That's like a meaner way of putting it, but it is a real way. Okay. She recently became single and has a one year old again, navigating a part of life that I can't understand. I can't understand being a 23 year old woman with a 1 year old. I look at that, that's like, that's like a, that would put me into fear like that, like I, the, the prospect of that. I go, oh, oh, oh, oh, oh, I, I'm, I, I, I would say good, you know, good luck to you would be my response. An honest response. A response that only works over podcasts. Like if in the comments section if someone's like, hey, here's my 20, here's my newborn, I'm 22. And a comment was like, good luck to you. You'd be like that person. And I'm saying it right now. And, and I'm hoping you're hearing the intent of like, oh my God, okay, you're 28, you're married to their, or you're going to get married to their brother. The 23 year old is sitting there single recently with a one year old. Single with a one year old. Something happened that wasn't the, the, you know, I don't think people Again, my personal opinion, young baby, when you're single you go, okay, did you choose to have it alone? Did you choose, did you a breakup happen that you didn't expect? I don't think you go into a baby expecting to be with, without your partner in, in some sort of way, you know, you don't expect a breakup to come. I would think not. Again, these are all, these are all biases. But then they're not personal to the person. Like I didn't look them up and down and go, well, one year old with a baby. I'm just hearing the facts and then my biases come. Okay, I'll stop vamping. But I, I do think these are important to like let off again as a. This is an alone show that I do daily and if you're new here, this is how we go through the emails for advice to just give you one what's going on in my brain because when I say these things out loud I go. I'm assuming the general people would say the same things but maybe not say them. She recently became single and has a one year old. I see her as a little sister, a friend, sometimes an equal since we're in similar stages of life. I get that if, if maybe you are you have a fiance and you have a child. Okay, 23 doesn't even matter anymore. She also lives within 10 minutes while my sisters are all hours away. So this is a companion of sorts. This is a female figure that you can talk about what you would want to talk about with a sister that is close by. I get that my friends and I would love to spend more time with her, whether that's girls night out, going to the bars or just hanging out with and without her baby. Well, I don't think the baby's coming to the bar with you and the gals for a girls night out, but yeah, I, I hear you. She has friends of her own, but they're often busy and they're often busy and I want to be supportive now and through the future. Well, her friends are also to go back and again admitted assumptions. Her friends are 23 and maybe without a baby so their concerns and their worldview is probably way different than you probably are. A pleasure for her to hang out, I would assume. The listener writes how can I support her as both a family and a friend without overstepping overall navigate this relationship. Thanks so much. You know that question which could have gone deeper didn't that's okay. I made more assumptions than the question even had. But you're saying you know it's written with you know when you write it the way you wrote it. How can I support her as both family and a friend without overstepping? I think this is like way more simple. I again, I don't know all the information you might say you might be because you looks like you're treading lightly and I would understand treading lightly when she recently became single and has a one year old. Hey, I, I know she needs some sort of help, but I don't Want her thinking herself as a pity project. That's. Those are like totally normal ways of think again. That's why I'm saying the things I'm saying. I'm not looking at a 23 year old with a 1 year old and going, oh my God, I pity their life. I'm looking at them going, hey, they might need some extra help, they might need some extra care, some, some hugs, you know, some, some. And also some help that I never needed. And I think allowing yourself to think that way also allows yourself to be compassionate to them and what they're going through. So how can I support her as a, both a family and a friend without overstepping? I think letting her know I'm here for you, you have my number. And letting her know that, listen, having a one year old and being single, I'm sure comes with some, with some insecurities. I don't think say insecurities. But if you want to be, I would say I would let them know you can't understand what it is to be in their shoes. I think that's helpful. Hey, I don't know how you know you want to be helped, but know that I'm here to help you is like a really nice way to put it. I don't know how, but everyone needs help. And letting her know that she's not alone, everyone needs a hand. Whether it's friendship, whether it's, you know, more logistical, whether it's just the listening ear. I think you, you say to her something along those lines, I am here for you. And then list it. You what you listed to me. If you ever need a girls night out or just want to hang out on the couch and watch some bravo, just know that I'm here for you, baby or no baby. You find a sitter, no sitter. You want to have your night away from things, just know that I'm here. And it's not just because you're my brother's or my brother, not just because you're my fiance's sister, but also because I kind of need you. My sisters are hours away. You say that I see her as a sister, a friend and sometimes an equal. She also lives within 10 minutes while my sister are all hours away. So I don't think you have to say I am your sister because I'm close. I think like the reference to hey, my sisters are miles away. So I always make it personal, vulnerable. This is vulnerable invites vulnerable. Hey, my sisters are all miles away and I feel a little lonely sometimes. So I can Understand if you ever have that feeling like I'm here for you, you have my number. I don't want to press because I don't want to like become a nudge and bother you. You're 23. Maybe there are things you want to do that you think I want, don't want to be a part of. But I'm around. Use me. I think that's in the same way I say for this podcast. This podcast is here for you. Email in. Hey, I'm the podcast. I'm here to be some sort of relief for your life. I'm here to get you through some of the anxious times right here. And, and listen, you might be emailing me a year from now. Oh my God. My, my sister in law is a giant pain in the ass. She took my invitation and totally took advantage of it. We'll cross that bridge when we get to it. I think for now you want to be a non judgment ear and you got to let her know that. J train podcast gmail.com j train podcast gmail.com Three emails as usual. Keep sending them in. I'm on the road. If you're listening right now, you enjoy the perspective. You're going to love the comedy show. I mean stand up, you know. That's why I do this show, to have a direct line to you, the listener to come to a show. West Hampton this weekend, Doral, Florida. That's near Miami. Red Bank, New Jersey. I'm doing like my weird Northeast American tour. Red Bank, New Jersey. Foxwoods, Portland, Maine. Huntington, Long Island. There'll be more dates added. I'm talking about being on a GLP1 and body issues and my parents. I mean, those are all things I've done in the past. I like the story I'm telling. I'm adding to it. I'm making it better. I'm feeling really good about it. Let's do another email before we do. We are sponsored. When you run a business, every missed call is a missed opportunity. That's why today's episode is brought to you by quo, the business communication system built so you never miss a call. QUO is the number one rated business phone system built to work on your phone and computer so you can respond anywhere and anytime. Get calls, texts, voicemails, transcripts and contact details all in one place. From solo operators to growing teams, QUO takes you to the next level. QUO automatically logs calls, generates summaries and flags next steps. It can even respond after hours so nothing falls through the cracks. Replies happen faster and customers actually feel taken Care of. This is a great thing to get involved with for your small business, especially this time of year. You know, summer hours. Quo. There are no summer hours. Communicate faster, stay aligned and deliver results with Quo. Try it today and see why. Quo is trusted by more than 90,000 businesses. Money is on the line. Always say hello with quo. Try quo for free. Plus get 20% off your first six months when you go to quo.com j j train that's quo.com j train quo. No missed calls, no missed customers. Let's do the next email. Jared, Big fan. Love it. Thank you for writing into the show. I've seen you several times when you come to Pittsburgh. Love the berg. Come back. I'm writing for Mailbag Monday. Okay, we're here. I have a best male friend, 43, that I've known forever over 20 years, since we were in college. Got it. So you're around my age, you have a male friend from college. In all the times I've known him, he has literally never had a girlfriend or even a date back in college. And right after he would make friends with these girls that I think in his mind were the start of a relationship, but they definitely just had him friend zoned. They would then find relationships and he would get angry and stop being friends with them. Since his early 20s to now, I've never even known him to have that. Since his early 20s to now, I've never even known him to have that. All his friends, besides me and my husband are men or old ladies who hang out at his dive bar. I think the problem is that he has so little self esteem that he is already afraid of getting rejected. Well, I guess that, that is if we were to like kind of dive into. Why do people engage in the friend zone? It's to miss, you know, to avoid the bullet of rejection. You know, if we were to think a little bit deeper, you know, and we all don't. I don't. It's hard. It's, it's, you know, the minute you start going down that little hole in your brain, you feel horrible and so you avoid that hole. So, you know, but if any of us, all of us listening or, or you know, to this podcast, who have ever been in the friend zone, if you thought of like why you did the friend zone or why you went that route, it was to avoid the conflict, you know, to avoid the answer to your question, do they like me as more than a friend? Is really tough to ask and to get it. And you can always get that answer. Why do people not get answers to the questions that they can easily ask because they don't want to hear those answers. That's why. So you become a friend. You go, oh, we're just friends. And, and, and. And at some point, while I sit here as their friend, they'll come to and realize that I'm the wonderful person they should be with forever or the person they should view in this way that I view them. You're hoping for a different result. And it's not a plan. It's not a way to get an answer. And we all know that I'm not smart. I went to a state school. I didn't even get a 3.0 average. I had to go into the economics program because I couldn't get into the business school because I didn't have the gpa. I am an idiot. I don't know more than you. I know just as much as you. And you and I both know the friend zone is because the person who likes the other person is afraid to hear that that person doesn't like them. Nobody is put in the friend zone. That's the problem with the friend zone. We all say it wrong. I put myself in the friend zone is what we should all be saying. No one did this to you. It was your choice between hearing rejection and becoming their friend. You chose the friend route, the safer option. So you wrote this in. We all know this. Does he want to admit that? He doesn't have to. He knows it, too. Whenever I bring it up to him, hey, tough that he should try to date again. You're avoiding. You should try and date. Oh, really? I'm 43. I didn't think of that. You think you're braver than him? You're as. You're as much of a wuss as he is. Hey, you should try and date. Oh, you know, I didn't think of that. I've been sitting here my whole adult life alone. I thought I should just become friends with people and they would realize what a wonderful person I am and how I could probably make them come because I'll do anything they want. But. But this whole date thing is. Is probably something I should have thought of 20 years ago. Yeah, they're not. So, again, like, we all point the finger, but we're just as much of a wuss. He just says he doesn't need the drama. I've even tried to set him up a few times with girls who are willing to go out with him, but he would never agree to go along. I'm not saying you have to be in a relationship to be fulfilled. But I feel like he's just hiding from it and will end up old and alone. I, I would also say you don't know what's going on. As it is, the older we get, the more often he is just a third wheel with me and my husband. He isn't the most attractive guy in the world. Photo attached for context. I mean, the attraction doesn't matter. That doesn't, that doesn't even play into my thought process of what they look like. Anytime you ask a dating question and someone asks what they look like, they're not a thoughtful dating answer. That's just a stupid. The looks do not matter in when it comes to dating questions. That is like a billionth on my list that I think of. That is him on the right with my husband and me. Yeah, I, I, I can look at the picture. I see you and the husband and the friend, but there's definitely someone out there who would date him. I mean, I have to say to you, I. Nobody single wants to hear the sentence. There's definitely someone out there who would date you. Who would date you. That is the lap. And again, single people, people with insecurities, have really good hearing. I, being one of them, hear very well. I would not want to hear, there's got to be someone who would date you. There's definitely someone who would date you. I think you, I think I get. This is feedback. This is gentle feedback. And I know you're trying to help your friend, but sometimes the most helpful people are the ones who get it the least. And they, sometimes people help people because they are personally motivated and they say they want to be the one. You know, there's a little bit of greed there. What advice should I give them or should I just stay out of it completely? Can't wait for your sage wisdom. Listen, I appreciate you writing in, and I didn't, I hope you didn't take me your, my feedback. I mean, I don't know how you avoid sounding a little bit. I don't have the word for it. A little demeaning. You're talking about your friend who's 43 and never had a girlfriend and he's just the third wheel and there's got to be someone out there. I mean, I'm even changing your words when you say there's definitely someone out there who would date him. It's. I don't think you know all the facts here. That, that's my feedback to you. What advice should I give him I don't think you should give any advice because we don't know what's going on. You know, before when I was younger, I didn't even know that asexual existed. But that's, that's something on a, in a mess of answers. That's one of the answers. But you do say that he gets mad when the person he has friend zoned finds a relationship. But that could be a reaction to his own, to not knowing what's going on in his head. I mean, to me, you know, the, you know, the advice to give him is to speak to someone like a professional because if he's getting mad, I, I, I think stick with what we know. If you, because something you wrote, they would then find relationships and he would get angry and stop being friends with them. That's what I would zone in on. On what? I know you get angry and you stop being friends with Marsha. Why is that? That's where my questions. I think you saying there's definitely someone out there who would date him. We don't know if he even wants to date someone. I think if you wanted to be a friend, it's, let's attack the thing we know you are angry right now. I'm really sorry you're angry. Can you talk more about what that's Even if you enter this whole conversation? Because my most, you know, the advice is really to be his friend. If you, you know, I would also say why are you and your husband friends with him? Do you enjoy your time with him? Is, is, are you hanging out with him? Because if you don't hang out with them, no one will. I don't know. Like, I think that's like a, I think a little soul searching is in store for you too. I, I know you, you wrote in about your friend who can't find someone, but he's not. He can't find someone would describe someone who's looking. It doesn't sound like he's looking. And if he hangs out with the people in the bar and you guys don't want to be in the bar, you know, what is this friendship that you have with him? And I'm sure he's a great guy. I, I feel for him because I listen these, you know, this, this exists. I, you know, I, I spoke a lot over the last year, especially on Coffee with J Train, which is my personal diary. And I get very personal and I, it's a, it's a, a lot of going in my head. If you and, and just thinking of like why I make the decisions. I do. And I talked about buying the apartment that I sit in now. And I talk about the. The decision between getting a place that doesn't challenge me versus a place that challenges me, challenges me financially, creatively. And when I saw the apartment and I'm again, I'm relating this guy moving forward with his life to me purchasing an apartment. And if you can follow me to this area, you might be able to understand him where he's opting for easy. Because I remember I was looking at places that were, you know, in high rises in Delray beach where I could afford, as I stand here today, to maybe also get a smaller place in New York and split my time between the two and live on as I was living. And if I wanted to make a change in my life to live, I could be that happy forever or I could risk that happy to have a really fulfilled life. And I took the risk. And that was hard. And even sometimes some days I sit here going, man, it would be. I kind of look back at that. I think a lot of, you know, I. I'll speak specifically to men I come in contact with that are married with kids, and they used to talk to me when I was single and be like, you know, they'd have that moment where you could see that they were like, ooh, that sounds good, but. It sounds good. I think like a hot dog sounds good. You know, a hot dog sounds delicious on a Saturday, but do I want a hot dog on Tuesday, you know, at 8:00 clock at night? Or do I want to have, like, chicken so that I can feel good, you know, throughout the week? Again, these are so. I think your friend might be dealing with that. You know, he can go to the same bar, see the same people and have easy conversations. And he, as he says he's avoiding the drama. That's an easy way to say I'm avoiding having to grow in my life. And discomfort that comes with growing and comes with not knowing if I can afford a family or a girlfriend or heartbreak or, you know, no chances taken. No chances. You know. You know, what is. There's got to be a saying for that. No chances taken. So I think if I was dealing with this friend, I would notice what you're noticing. I would let them know I'm here for you in any way I could be here for you. I would also, if they do come to me with an emotion, I would attack that emotion as a friend. So I'm. If he's angry that his friend, again, I use the Name? Marcia. Who knows that Marsha's in a relationship. I'm not going to be friends with her anymore. Can you talk to me about that? That's. I. I thought you were friends. You know, I think you can investigate that. I think getting into. He's not the most attractive and he's never had a girlfriend. We don't know. He might be asexual. He might not be needing that. He might be so afraid of. Of being turned down that he just. Why try in the first place? We don't know. I. I think we're missing information. He might be questioning his own sexuality. You don't know. He might have kissed a woman and been like, oh, my God, I don't like it. But I don't want to know what's on the other end of that. And then I don't want to open that Pandora's box that becomes, you know, a different life than I imagined for myself. All of those things are at play. But I. I think as a friend, I would. I would challenge you. Why are you friends with him? And to have fun with you and your husband and him in those ways. And if you're not having fun with him, I think you gotta, you know, maybe you gotta move on from the friendship, as sad as that is, because. Are you just with someone that you pity? I don't know. This is really tough. 1. I feel. I feel for them, but I feel for this guy in the way. Because I don't. I don't want that for my life. I don't know what he wants for his life. Life maybe, though. Are you having those con. What do you want from your life? What do you. I think getting away from relationship and girls, I think that's a. That's my best piece of advice. I think anytime you bring up someone specific for him to get with or to be with and whether he wants a relationship, it's not going to help. And you're going to sound bad. He isn't the most attractive guy in the world, but there's definitely someone out there who would date him. Is a sentence that would cripple me to my core. J train podcast gmail.com. j train podcast@gmail.com. let's do one more. We do three every week. Join the Patreon if you want to get to know me better. Five bucks a month, plus you get first dibs on Tik Tok Tuesday. Jared, I need your help with a reveal. Ooh, the reveal from the book Walking Red flag. I've been talking to a Guy from Hinge. Since mid May, as I sit here reading this. June 22nd, we spent about two weeks having really substantial conversations on the app before meeting in person. Since our first date, we've texted every day and have now gone on two dates. That is two different things. Let me give you some light feedback. Since our first date, we've texted every day and have now gone on two dates. Let me assume, best case scenario, you've been on three dates and you met each other over the app. Mid May, May 15, June 22. I'm sitting here. A month and a half. You've been on three dates but text every day. I think we have to come to terms with. Effort is not through the fingers. It's through the feet. So effort not on the fingers. In the feet. Unless they use their feet to use their fingers on your genitals. That's effort with consent, obviously. So that's. Let's stick to that. Right now, you've been on three dates with someone. There's a lot more effort going on in the fingers than the feet. Those are two. We've texted every day means nothing. We've been on three dates in the span of a month and a half means something. We've been on three dates in the span of a month and a half and we text every day. There's a lot there and it's not good. He's dating other people. That's okay. We can date other people and still date one person from those other people. And that can be a relationship. It can happen. I'm not saying it's over, but I'm saying right now, the way you're judging how this is going might be fraudulent. Both dates last. Oh. Where? We've been on two dates. Two dates, a month and a half. Text it every day. We have a problem. Both dates last around three hours. I don't care. Two dates is two dates is two dates. And the conversation has been that rare combination of fun, easy, and surprisingly deep. We have a lot in common, and I genuinely enjoy getting to know him. Here's the complication. Right now, I would say you've been on two great dates with a guy that has come over the span of a month and a half. We have a problem. You're not seeing each other enough. Here's the complication. In about 10 days, I'm leaving for my family's beach house for four weeks. I do this every summer because I work remotely, so it's not a surprise. But it does mean we'll be apart for a month. At very early stage of dating, I would say you're not dating two dates over the course of a month and a half. No matter how good those conversations are. I need more in. In person time. I've realized I've already made some decisions on my side. I've paused my hinge profile, stop pursuing other conversations, and honestly have no interest in dating anyone else while I'm on. While I'm home. I'd rather keep getting to know him. But I have told. But I haven't told him any of that. Yeah, I think that's okay. But two dates might not be enough for him to keep his concentration on you. But his concentration is not as important. And because I haven't told him, my brain starts filling in the blanks. Will he keep dating while I'm gone? Will he meet someone else? Will a month apart be too much effort for someone? It's not about effort. It's about. See, this is where the. If he wanted to, he would really breaks down. Will a month apart be too much effort for something that's only two dates in. I think your concern is in the wrong place. This feels like the perfect situation for what you've described as the reveal. Yeah, I. I would say it is. But I think you need to be cognizant of what you're asking for and what you're also not asking for. Why aren't you asking for more time in person while you're here and not moved away for the summer? And here's the thing. And here's the if he wanted to, he would. If he wanted to, he would. Falls flat. Because that lives in a world of zero other options where it's tough to find options. What you're asking for is for someone to go, please be with me. Please be with me. And then take on all the responsibility of that decision while there are easier decisions to make otherwise. Hey, let's push this off. Isn't that he doesn't like you, but it's also that we're not making a. You know, the, the stakes are not the same. Your stakes of being told to be in a relationship with him are not the same as him telling you to be in a relationship with him. The stakes are uneven, but also. But morally, your stakes are also unevenly uneven with his. Hey, I'm not sure. Not really that great. Hey, I'm so sure. Based on these two dates, you seem like a great person. I'm. I'm just giving you the other side feedback on that. This feels like the perfect situation for what you described as the reveal, but I'm struggling with how to do it. I don't want to tell him what to do. I don't want to demand exclusivity. I don't want to have the talk. What I want is to share where I'm at. I think you need to read the book if you haven't already. I'd love to keep texting while I'm away, maybe have a few phone calls or phone walks and continue to get to know each other. I also want him to know that I'm not planning to spend the next month on hinge looking for other options. So my question is, do what does a good reveal look like here? How do I tell someone I like where this is going and I'd love to keep investing in it while I'm away without turning it into a relationship definition, a conversation or asking for reassurance. Thanks. A girl heading to the shore Leaving boy in the Midwest. I don't think you've been on enough dates. That's my initial thing. I don't know why you been on two dates and you know in 10 days you could have gone. You have a lot of dates to go on if you are being. And again, all things can happen. You can go on two dates over the course of a month and a half and end up in a relationship with that person. That can happen. I would say for you to be as swept away as you are and you're looking beyond the 10 days you have here and now that you can spend time together, you could literally spend. And again, this happens. This happens. And it's not that crazy to say we've hung out every day until I left and it's been wonderful and magical. I think you are so held up on this trip that's coming up that you're not even looking at what you can control now, which is, hey, I would love to spend more time with you. I enjoy our two dates. Let's go on a third before I go. That's not that big of a deal. Let's go for a walk. Why aren't you going on like where. What is going on in these 10 days? That's my feedback. You can do the reveal. The reveal is easy. You wrote it already. Read this script. You wrote the reveal. I've paused my hinge profile and stopped pursuing other conversation and honestly have no interest in dating anyone else while I'm home. I'd rather keep getting to know you, but I haven't told any of them that I would read that sentence. That's the reveal. Oh, the scariest one is the one I should do the most. Yes. Sorry. Sorry to inform you, but I think that happens after these 10 days when you are two people who are everyone's busy, but you're two people with enough time to go for coffee in the morning before you go to work. You're two people with enough time to get together and watch TV on the couch before you go 10 days from now. You're two people who can go get a bite to eat. You're two people that can get a bite to eat, not have a sleepover. You're two people that can have a sleepover with no bite to eat. You're two people that can go to the movies together. You're two people that can go get, you know, go get an ice cream. What's with those 10 days? That's my question. At the end of those 10 days, I would say, wow. And at the end of those 10 days and I still feel this way, hey, I'm about to go for a month to a family summer vacation spot. I just want to let you know I've paused my hinge and I'm not really, I'm not pursuing other conversations and I really don't have any interest in getting to know anyone else while I'm getting to know you. And then you stop talking, Let them talk. And then I think worst case scenario, they blabber along and they don't give you an answer and they don't make you feel loved, then you have to kind of feel that and take that information in and, and make a decision from there. Or they blabber on and then, oh, you know, a day later, hey, I've been thinking about what you said, and, you know, I, I think it's too much, too soon for me. Or best case scenario, hey, I feel the same way. Our dates have been wonderful these last 10 days where we finally got to hang out on a more consistent basis has made me feel the same way. How can we figure out this summer? How can we figure out this summer is where you want to be? It doesn't need to be where you be. It is where you would want to be. I think that would be a. But it has to come after you feeling really good about what they say back to you. How can we figure out this summer? Well, you know, I'm going to come back this, you know, in two weeks and you're going to, maybe you can come in three weeks. And, you know, those are all buyers decisions. But before that, I gotta ask you, what are the 10 days? What are you doing two dates in a month and a half? I don't think are enough. I think you're gonna. I don't think. I don't believe in too soon. You can still have the reveal, but I think that mountain for them to climb over, I would be like, I don't know again. The, the connection might be so great, but something's off about two dates in a month and a half where you're this swept away and they're not swept away enough to make more plans. J train podcast gmail.com j train podcast gmail.com we'll be back next week. Keep sending your emails. Boom.
Host: Jared Freid
Date: June 29, 2026
Episode Focus: Jared answers listener emails about relationships, friend dynamics, and dating, offering his signature candid, humorous, and practical advice.
This Monday Mailbag episode revolves around the complexities of relationships—romantic, familial, and platonic—through answering three anonymous listener emails. Jared unpacks:
Throughout, Jared leans into his forthright, relatable tone: he’s open about people’s motivations, fears, and social dynamics, and never shies away from giving the honest advice he would want for himself.
Email Summary:
A 28-year-old woman seeks advice on supporting her 23-year-old fiancé’s sister, who is newly single and has a one-year-old. The two live close by, and the emailer wants to balance supporting her as family and friend—without overstepping.
Email Summary:
A woman asks whether and how to help her long-time male friend who has never dated, avoids romantic risk, and often ends friendships with women who find partners. She wonders if she should intervene or simply let him be.
Email Summary:
A woman just started seeing a guy (two dates in 1.5 months; texting daily). She’s about to leave for four weeks of summer travel. She’s interested in telling him she wants to keep up momentum (the “reveal”) but doesn’t want to be pushy or demand exclusivity.
“You wrote the reveal. …‘I’ve paused my Hinge profile, stopped pursuing other conversations, and honestly have no interest in dating anyone else while I’m home. I’d rather keep getting to know you.' …Read that sentence. That’s the reveal.” (53:50)
On Relatability and Assumptions:
“This is an alone show that I do daily…and if you’re new here, this is how we go through the emails for advice—to just give you what’s going on in my brain, because when I say these things out loud, I go, I’m assuming the general people would say the same things but maybe not say them.” (06:01)
On Friend Zone Dynamics:
“No one is put in the friend zone. That’s the problem with the friend zone–we all say it wrong. I put myself in the friend zone is what we should all be saying.” (21:03)
On Relationship Effort:
“Effort is not through the fingers. It’s through the feet.” (44:24)
On Compassionate Invitation for Vulnerability:
“Vulnerable invites vulnerable.” (10:45)
| Segment | Topic | Timestamp | |---|---|---| | Opening & Purpose | Podcast’s mailbag format, types of questions | 00:00–01:23 | | Email 1: Sister-In-Law | Navigating age gap, supporting without overstepping | 00:41–13:17 | | Email 2: 43-Year-Old Friend | Friend zone, self-esteem, when to step in | 16:48–38:50 | | Email 3: The Reveal & Summer Travel | Early dating, making intentions clear | 41:22–1:01:26 |
Jared brings the empathetic, no-BS perspective he’s known for to three relatable listener dilemmas. Expect candid breakdowns of motives on all sides, a focus on autonomy and authenticity, and permission to be real about your needs with friends, family, and romantic partners. If you left the episode with only one lesson, it’d be:
“If it feels scary to say, that’s probably the thing you most need to share.” (Paraphrased, 55:30)