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It's a mailbag, Munder. You got problems there. I'm gonna help you from the comfort of my chair. It's a mailbag Monday. Hello and welcome to the J Train Podcast. This is Jay Train Jared Freed coming to you live from Delray Beach, Florida. That's right, every Monday is a mailbag Monday, where you' or email me the comedian with your questions. That can be any question you have. We do all types of questions. Really. You'd say, well, you know, the. The response might be, why would anyone send a question to you? Well, something's on your mind. You want to hear it out loud. You want to hear someone who doesn't know you. Just hash it out in a fair way that I'm not thinking about how you used to act in college. And I'm not thinking of whether you are a mess with your, you know, your apartment. I'm not thinking of what your car looks like in the passenger seat has a bunch of McDonald's wrappers. You know, I'm not using that to give you my opinion. I have the email. That's it. I got your words, the ones that you chose. So if you have a question, email J train podcast gmail.com. that's always appreciated. Relationships, friendship, drama, wedding stuff, bachelor party stuff. Anything you're going through, family, friends, all that stuff, send it in. I am taping this. It's Monday, May 18th. I'm taping this. It's coming on the 25th. The book tour. The book tour. The book tour. If you are in New York city, Boston, Philly, D.C. chicago, Denver, we're gonna have a book tour. Walking red flag I'm holding in my hand, you can order the book. Pre order the book. If you want me to do a cameo for you or the. The pre order campaign was I want you to order the book for a friend and I'll make a cameo for the friend. If you want to do that. Still available, just DM me. I'll get back to you. Friend. Friend's name and a fun fact. That's all I need. I'll make you a video where I talk directly to your buddy and let them know that you got them the book. Also let me know if they're single or not. That's kind of helpful. That might be helpful. So book tour, book tour, Book tour. If you are in Austin, Texas, I will be there this weekend. Cleveland, the Hamptons, Miami, Red Bank, New Jersey, Foxwoods Casino, Portland, Maine. So those cities are all coming up. Order the book, Come to a show. Let's do the emails. I got three emails. This one's a. This one's hefty and I got two sponsors. Jared, Longtime listener, huge fan, Patreon subscriber. Have been to several of your shows. Now for my question. I have a family friend from my hometown. Our parents are close, but we didn't really get to know each other until a couple years ago. The first time I met him, I immediately thought he was super cool, smart, funny, social. Just really good energy. We exchanged numbers because we both live in the same city and would occasionally text or see each other at family events. The last time I saw him before recently he was with his girlfriend of three years. So I fully filed him away mentally as unavailable. Sounds like there's about to be a change with your family friend. Fast forward to my birthday a couple weeks ago. Happy birthday. He texted me and asked if I wanted to grab dinner or drink sometime. I was excited, but also genuinely had no idea what the intention was because as far as I knew this guy still had a girlfriend. We ended up at dinner for over two hours just talking non stop. Then went to another bar for drinks after. That's when he casually mentioned his now ex girlfriend. I mean if it took you two hours to figure out that he wasn't in a relationship anymore. He just didn't mention the person that he's in love with the for two hours that the person that he's like working towards a future with for two hours. No, he is single. And if he wasn't single, I mean he was about to be. Turns out they broke up in February. So I'm sitting here May 18th February breakup. Okay, spring flowers brought along this doodaloo. I also get out got out of a rough situationship recently. So we started talking about relationships and dating. Suddenly the whole night shifted into feeling very daty. Lots of arm touching. Well, I would say to you I and I know this is a woman writing in because I can. Well I think you already said you it was a woman but I, I will say the need for categorization. The need for. I mean you wrote I fully filed him away mentally as unavailable. I think that is very female to me. I'm. I'm just giving feedback on things I've heard in the past. Everything. That's my best friend. That's my friend from college. That's my friend from my best friend. Not best friend people. It is all boxed up neat and tidy almost to a fault. So it doesn't really let you let go this guy. You know, when I. You. When I'VE been out on dates. I'm just out. I'm just with someone on, you know. You know. He called you. Some chick I called. I'm going out with her. Oh. Family friend. We'll see what happens. I just. There's a, there's a. There's a organization that a lot of women tend to do where. I mean, you were in a rough situationship recently. I was in that. And we started talking about relations and it's like suddenly shifted into feeling very daty. He asked you out to dinner and drinks. That is the fact that this didn't feel daty before that. Like, let it happen, let it be. Lots of arm touching, long eye contact, huge smiles, etc, were together for almost four hours total. And honestly I feel like I was floating. I left. Let me read that sentence again. It's important. We were together for almost four hours total and honestly I left feeling like I was floating. I love that I've gone on other dates recently trying to get back out there, but nothing felt as remotely like this. Nothing has felt remotely like this. This felt easy, exciting and safe at the same time. At the end of the night, it felt like there maybe could have been a kiss. But I think we both held back a little because our families know each other, which definitely. Because our families know each other, which definitely ups the stakes. Now here's my issue. He's going away with his family for like 10 days and I'm trying not to spiral because I already know him outside of dating. I already know he's the kind of guy I could genuinely see myself with. Again, box neat, tidy organization. I know he's the kind of guy I could genuinely see myself with. She's already, she's already lived out that fantasy. She's being, she's being. She's not even admitting she's already watched herself walk down the aisle with this guy. It's. Which is totally fine. Like, I am. Let me. I hope I don't sound like I'm being negative. I. This is not. I'm just assessing the situation. I'm looking at what the words she's putting down and I'm telling her her problem right now is. Is constriction. The organization feels like it's her problem. 10 day vacation with his family. I don't, I don't. 10 days with you. And I do say it. Beware of vacations because it creates space, it lets people think. It goes, you know, you go, oh, well, I can get away from that person and they'll forget about me. A Little bit. And it won't be, you know, out of the blue if I say, hey, I don't want to go out anymore. That's what a vacation does. Gives you space so that you have a reason. But I also. It goes the other way too. No, you know, no vacation is the reason someone doesn't, you know, date someone that they like. The vacation is the excuse to get away from someone you've already decided you don't want to date. So the vacation is here nor there, but. Okay. I could genuinely see myself with. He checks a lot of boxes again. I'm neat and tidy, but I'm also not trying to emotionally masturbate the situation after one day. You already have. It's okay. I think it's okay to emotionally masturbate. Enjoy you ha. Let's look at the positive. I know I've been negative now. I've been, I've been. I've been a realistic Ricky so far. That's who I've been. I've been. I've been Riley Real. I've been Joe Rogan real, real time. I don't know. I'm looking for other our names. I use the most divisive name. No, I. I'm being, you know, I'm being Rodney Real. And let me be, Let me be Erica Excitement, Eric. Excitement. For two seconds, you went on an awesome date with someone whose company you truly enjoyed. And they are someone that you want to see again. Hooray. Yes. We did it. The dream. An arm touching date. Baby girl, we love it. That's what it's all about. And, and there's reasons you felt comfortable. You guys have, you have safety, you, you. Everyone wants a safe adventure. This guy is a family. You know, trust, understand, you know that he's not going to do wrong by his family. You know that your family knows him. And he's not going to want to embarrass his family name. He wasn't going to embarrass his family by being a douche to you. But he also was new enough and unknown enough that he was an adventure. He's a safe adventure, which is what we all want. We want a tightrope walk with a net underneath. And this guy gave you all of that. You could go on the date. Wait, is he in a relationship? Is he not a relationship? Oh, my God. He's touching my arm. This. They broke up in February. Holy shit. His family's cool. I get along with his mom. There's a lot of great here. And it's okay to get Carried away a little bit. What's the best move with texting while he's away? I don't want to overdo it, but I also don't want to act weirdly detached when he clear when we clearly had a great time. Also because this is a family friend situation, I haven't told my family yet because I don't want everyone to get invested after one date. Would love your thoughts. Thanks. Totally understandable. My thoughts with texting is if you have something to say, say it. No text you send that is sent thoughtfully, happily and energized is going to be the reason this ends. There is no text you can send to screw this up. Literally you. Unless it's just being mean, which you're not going to be. There is no text that you can send to this guy that is going to be the reason you guys ended because I trust that you want to get to know him. Want to keep talking, want to go out again. You're going to do fine. Listen, you went on a four hour date. Let me, let me, let me just give you. Let's go back to Rodney. Real 4 hour date doesn't matter. He reached out to you to make a plan. Does matter. You have family that you guys all know. He let. Let's think of him for a second. I'm all over the place a little bit, but I would say the positives are he. What you're saying is that you haven't told your family because you don't want everyone to get invested. He looked beyond the fact that this is going to be a giant mess. Dating someone who knows my parents and I know her parents. And he said, you know what? I'm attracted enough and and thought and think highly enough of her to go who cares what will be will be. So he took a real chance. So that's great. You also share a lot of memories and a lot of things in common that make it feel way more lived in than it is. So you're ahead of yourself because you know the same street signs, you know the same cousins, you know, whatever, you know, you know his mom's name. So acknowledge that. Let's acknowledge two things at once. The good, he took a chance by asking you out and doing this date. And two, you're a little ahead of yourself because you share a lot of things in common that you wouldn't share with someone off a dating app. So those two things are important. But I really think texting him, if you have a thought that comes to mind that makes you think of him, text it don't even like a sneeze. Just do it, do it. You can't fuck it up. I would also say to you, let's get a date on the calendar. Let's let him know. Let's be a little bit more vulnerable than we're being. Let's let him know. Hey, I've been thinking about our date and it was just a really great time and I, I'm excited to get together again whenever you're back. Let's make a plan. Make a plan. And I'll make sure my calendar can, can work out for that. So I think put the cards on the table. We want this to fail quickly again. You said you're not telling your family. I, I'm kind of, I'm okay with that. Let's get, let's keep the family. That'll be fun. If it can be fun. You know, maybe a month from now you guys are dating and you go to your family like you're not going to believe this. I, I'm, I'm, I'm, I'm Jason, your friend. Your, your friend's son. Yeah, Great penis. You wouldn't believe it. I mean, you're not going to say that, but that, you know, that's going to be fun. You're going to be excited to tell your fan. Let's, let's, let's let that happen. But for now, I think you have to. Let's, let's, let's be romantic and realistic. The romantic is you got something to say, text it. You think of him, text it. I don't give a fuck about his 10 day vacation. There is no such thing as too much. There is no such thing as saying too much. There's no such thing as saying something weird or off. You guys had a four hour date where you know enough and you can think of enough things to say that will probably come to mind from that date that will make you think of him. And let's, you know, maybe he gets back to you and we'll judge him appropriately. Maybe he never gets back to you and you go, what the fuck? I guess you're a dick. I guess you didn't hook up after the date with your family friend. That's a weird way to go out and try to hook up. Like, you know, that could happen. So it's twofold. Text when you got something to say and I'm sure you got something to say and let's get a plan. Let's let him know you want that plan because he either makes it or he doesn't. And if he doesn't, you can kind of back away. And you know, maybe, maybe you say to him, hey, because of the family involved, I'm looking to go out again. And I let you know that I was vulnerable. But I'm not gonna like let this hang here because, you know, I got parents to answer to and they're and, and I got to see what events in the future this that's the beauty of knowing people in common is that it has to fail quickly. You're actually in a good spot if it does. J train podcast gmail.com j train podcast gmail.com quo. You shouldn't have to text, call and email your coworker to get a reply. That's why today's episode is brought to you by Quo, spelled Quo, the business communication system. Built so you never miss a call. Quo is the number one rated business phone system. The Quo app works on your phone or computer wherever you are. Calls, texts, voicemails, transcripts and contact details all go to one place. Communicate faster, stay aligned and deliver results with Quo. 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 train that's q-uo.com j train I got two more emails. Keep sending them in again the YouTube channel. We got standup videos every Saturday on my YouTube. Jared I'm a subscriber to both Patreon and Benefits. Thank you. Love your work, the laughs and advice for dating in 2026. I'm 36 year old widow. I was with my late husband from age 19 till his passing when I was 32. I am so sorry. That stinks. I've taken the past few years to work on myself and I'm ready to start dating. Well, welcome back. I'm really sorry again for your loss. That sucks. I mean 19 to 32. My questions are what are the best ways to communicate wanting a casual relationship? I've been married and widowed. I'm not looking for anything that serious right now. Should I be on the apps? Never use them. I recently went on to a speed dating event and realized many guys my age are looking for something I've already had or have. Marriage, kids, happily ever after, which I hope they find but not what I'm looking for. How do I date as someone who really never has and and when do I bring up being a widow? Appreciate any insights you have. Widow plea widow help please. P.S. saw you in Nashville last year. Love the show Hope you make it back on your next door. Well, thank you. Well, there. Let me just start by acknowledging there's a lot here. Let's start with, should I be on the apps? I've never been on the apps. How do I communicate? I want casual. How do I tell someone I've been, I'm widowed? I mean, holy. I mean, this is like seven emails in one. Let's start with you're not an idiot. I, I, that seems like pretty simple advice. I think a lot of people, when you say not, because right now I can tell by the way you tell your story. You're also telling people, I was. When you say 19 till 32, it, it. And I'm, I'm, I'm, I'm making an assumption based on things other people do. But I, that's all kind of how that's the only way I got to work. When people reference being 19 to 32 in any relationship, they kind of act like, oh, I've been locked away in this other world where I don't know anything. You know, when someone stops texting you, you know when someone's acting weird, you know when a friend or family member is just being off. All of those instincts are the same for when you're dating and when you're trying to hook. Hook up and when you're trying to meet people. So my first piece of advice is, you're not an idiot. Trust your instincts. Just because you've never dated doesn't mean you've never lived on earth. And that is a story that many, I have noticed many divorced and, and, and in your case, widowed. I, I think many people who didn't expect to be single at a certain age often tell themselves this story. They often tell themselves, well, I've been out of the game for so long, I don't even know what's this phone? How do I use it? And it's like, you're not new to earth. Let's, let's, you know, and I get it. You, you are, you, you are telling a romanticized tale. And I'm giving the general you. Because having a husband pass away or having a spouse pass away is horrible. And that is a story that I can't even imagine having to tell. And you know, I, and I'm sure it comes with tears and it comes with, you know, how you met and you were 19. Again, like, there's, I'm not trying to minimize your story because there is a story to tell, but sometimes we can believe in the story we tell a little too much. I think sometimes we can give, give in to our story and kind of self victimize and I think you sound like a very strong person so who went through something tragic and that, that happens to people a lot and we got to go get through it. So, so I'm, I'm giving you a little bit of tough talk and you're not an idiot. One, two. Speed dating event. Let's stop going to these. I, I, I know you, you're looking for ways to try and just being alive is trying. You don't need to go to a speed dating event. Let's cut that. I, I just, you want casual, which lucky for you, you're a woman. And that kind of is the default for most men who are dating that aren't signing up for a speed dating event. And, and like you and you, you seem to realize it very quickly. You said that you, these people on the speed dating event are looking for what you already had and have a marriage, kids, happy, happily ever after. I would say the first step for you, and this is something I write about in the book, is hanging out with friends and family. But you said you've been, you know this, you were 32 when your husband passed and now you're 36. So it's four years old, four years later. I, I would, that's my first move if I was to like do a pemdas here. Go to brunch with your most fun friends and let them know, you know, let them know that the, you know, the, the old cooch is back for business, so to speak. Have a flirty, fun brunch with the drinks flowing with friends. Let them know that you've been horny and you're looking to get out there. And I think this is an easier conversation amongst women than it is men. Like I think if I went out with my buddies and got a little drunk at brunch and I was like, I've just been so fucking horny lately, it would be disgusting. I think for women this is a little bit, I, I've never been, I mean, maybe I'm just imagining a porno that I had a dream about, but I, I do think that my assumptions might be true where you can go and get drunk with a few friends and let them know I'm just looking to get in a safe and casual situation, which is fine. So I think those people now become your henchmen and if they're married, that's fun for them. If they're in relationships, if they're dating someone, if they and, and they can kind of start to like, spread the word in their way that they can. I think that's your best group for that. Now downloading the dating app. Yeah, you should do it. I don't think you should say, I'm looking for casual. I, I wouldn't even answer that box. I think you can go out with men the first thing you want. Because I, I think everyone's definition of casual is different. If you say you want casual on a dating app, the version of casual you will get back from men is going to be, yeah, I'll sleep with you in an alleyway on top of a dumpster, and then we'll never see each other again. Oh, good, we're both looking for casual. I think your definition of casual is probably a little different than that. It's probably, I want safety. I want to feel a little cuddle. I want to feel excited. And I also don't want to have to call the guy and see, you know, what, what he's up to next week and have a, like an appointment that's on the calendar all the time. I, I think that's kind of the, the dream scenario for widowed woman who's kind of looking to like, have a little bit of fun and touch a testicle or two. So I, what I would say to you, go on the app, make a profile and, and let's get to. I think you can figure casual is to be figured out. It's not to be get gotten ahead of. If you get ahead of it, you are going to be like a bleeding, you know, fawn in the wild and the lions and tigers will pick up on that. And, and you don't want that. How do you say that you're a widow in whatever way you want to say it. I think someone has to earn that information. I think if you don't feel comfortable, I think going on a date with someone and if they don't even take the time to ask you about your past relationships, they obviously aren't even looking to be a fun date or a trustworthy date. I think if someone takes interest in you and you feel comfortable telling them. Yeah, let them know your story and how they react is where you get to judge. I think that's like the reversal. That's the power play. And not that you, you're looking, I think looking for a power play is, is, is a small time maneuver. But understanding that if someone doesn't react well to your story. 19 to 32. And now I'm back out here after working on Myself. If someone can't be caring and nurturing to that story, then they can't really handle being casual with you. And it's kind of a great way to figure out if someone's not for you or not. I'm not, you know, I'm not trying to like, again, this isn't. Your story is your weapon. Your story is your is, is your filter. So I hope that all helps. I do think woman on app looking for casual. That is again, another thing that someone has to earn. That's probably the best way to say it if I'm to review if, you know, I do these emails, I read them and I answer them off the cuff as we. I like to answer them as you hear them. But I would say if I was a woman looking for casual, that is like a power. Someone's got to earn that like that the end. And you might. And, and I guess the fear, the reason to say it up front is like, well, I don't want to fall too hard and I don't want to. Well, if you fall for someone that you thought you were going to be casual with, how great is that? What a. What a win. Why is that such a bad thing? Oh, but I wasn't ready. It's only been four years. Well, four. Feelings change. Allow them again. This is, this is same thing as the last email. Two people trying to organize too much. And I've done that. I listen, I'm, I'm, I'm one of those people too. But I, I think a lot of the, especially women write in. This is my home friends. This is my ex. That guy's in a relationship. I'm looking for casual. I just want to make sure I'm not like leading anyone on who's looking for more. You'll know. The idea that you don't know is crazy. I, I've been on dates. I've dated women. Been two months in. Oh, she, she wants more. I'm. I'm going to be rude if I go another month. We know. You know, I don't want more than another month with this person. That's hard to. That's hard to say. But if you try to get ahead of it, you are going to be let down by the type of people it attracts. 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You don't. So Rocket Money is going to let you know that and, and you're gonna, it's gonna sting. You're gonna sign up for Rocket Money. You're gonna go, oh, I've been paying for that for like six years. And then you're gonna stop paying for it and the bleeding's done. And now you get to feel good about yourself. So Rocket Money is a really good way to feel good about yourself. Do you want that? Sure. Rocket Money's dashboard makes it simple to manage checking, savings, loan and investment accounts with a clear view of your finances on one screen. Let Rocket Money help you reach your financial goals faster. Join@RocketMoney.com J Train that's RocketMoney.com J Train RocketMoney.com J Train that's our two sponsors last email Jared, longtime listener, you made the call for more advice emails. So here's my predicament. We always want advice emails. J Train podcast gmail.com A few months ago I, 40, female, visited my boyfriend's family. We've been together for five and a half years, choosing to be child free by choice. Zero pressure to rush down the aisle. And while I was there, my dad asked me to pick up my late grandmother's ring from my aunt and an uncle who had been holding on to it. It's stunning. A 2 carat center diamond surrounded by 20 smaller stones. Not my personal style, but still beautiful and sparkling with diamonds. At our next family dinner, my dad asked me to bring the ring out and proceeds to suggest that my brother, who is 35 and has explicitly said he wants to get married and have kids, could use the center stone to propose to his girlfriend and then I could have the smaller diamonds to make into earrings or something. Thing to me. I don't know what the email or where it's going to go. To me, this sounds like a very fair tribute to the the late grandmother while also kind of like helping everyone out. For context, my brother and his girlfriend have also been together for five and a half years. We actually started dating our partners about a month apart. He's already planning to propose on a trip this summer, but the rest of the family didn't know and know about this until this dinner. I told my dad that didn't feel fair and that I wanted the ring or at least the solitaire. So I guess the solitaire is the center is the center diamond. My dad looks sad and hurt by my reaction. My brother, bless his chill, golden heart child, also said it felt too soon to dismantle the ring. Okay, here's what's really eating at me. I'm the oldest daughter. I am the one who gets called first when anything goes wrong. I hold everything together and somehow I still end up feeling like an afterthought. Well, my brother waltzes in and gets put on a pedestal for simply existing. The fact that I'm not in a rush to get married and have chosen to not have kids apparently means I don't deserve a piece of our grandmother's legacy. We've agreed to get the ring of praise and figure it out from there, but I'm still not over it. Am I wrong for feeling like I should have been considered from the jump? First called, last considered eldest daughter. Well, I really appreciate the email. I think you said, am I wrong for feeling like I should have been considered from the jump? No, you're not wrong for your feelings. I can't say that to you. I can say you've made a lot my, my, my feedback is that you have a lot of issues with your family and the ring was the straw that broke the camel's back for all these issues. So I think the ring, you know, when you. Because I, I saw this as like, like, and, and I felt for your dad when you told him and he got sad. He didn't get angry so. Because in your dad's mind, he was like, I got this all figured out. She'll get this, he'll get that. We're all set. We got the ring, good to go. Like, and you have this already. I think your dad would be surprised to find out this is how you feel about the dynamic of the family. And when you say I'm the oldest daughter, I'm the one who gets called first for anything that goes wrong. Like, you know, if you haven't put up a fight to that to this day, this feels like it's like all coming pouring out of you, which, listen, you're entitled to your feelings. I hold everything together. Like, this is to me, like, where's my money for all the work I've been doing? And if people don't see it as work and they just see it as the dynamic of the family, they're going to be surprised to hear that you've been keeping a running tab. So I'm just telling you how it sounds. I'm not telling you you can't feel that way because it, it's, I, I'm going to trust you. This is how it's been operating. You're the oldest and you feel you should be compensated for all the service you've been doing. That's the way your email sounds. And I think if your family and, and I think also, like, you know, your brother, like, I, I'm going to come back at you a little bit because you say my brother, bless his chill, golden child heart, also said, so your brother took your side. And then you write to me that your brother waltzes in and gets put on a pedestal for simply existing. Like, you've kind of, like, you kind of on your brother. And I know you're saying that your parents are doing this for your brother, but, like, he's being good to you, like, he's looking to work with you, you know, So I don't know. I, I, I don't think the idea that you should have been considered from the jump, I, I don't think your parents would see it that way. They would, your parents are like, how do we keep this fair? And they're not really putting on the bill what you've put on the bill. So I don't know how you, I think you gotta take the ring out of the picture and kind of. Because right now you've set up a scenario where, and what I've just said, I'm not getting compensated for my services in a fair way. I don't think your family is gonna, like, take kindly to that. And I also don't think that they're gonna look at the bill the same way. They, they have a different bill in front of them that they think they're being fair. So I don't think they understand the load that you've been feeling like you're shouldering. And I think that's something you have to communicate to your family because maybe if they knew that, then they would have divvied up this ring in a different way. But to me, the, the ring is them showing you how them calling you first means nothing to them that the ring just showed what tab they've been building and how it doesn't match with yours. So do with that information what you will. You know, if you take that information, you go, hey, you up. You guys don't realize how much I do for this family. You, I don't know, you've created this like battle that I think is very difficult for you to win. Like do you want to be right or do you want to win? You know, that's kind of a decision you have to make. You might be right. I, I listen, I'm not going to deny your feelings. This family is annoying. They call you with all their problems. They expect you to fix it. They don't go to your brother for anything. All right, so what now that you have all that out of your system, what are we going to do here? Is it about the ring or is it about, hey, I want to be acknowledged that I just found out that none of you really acknowledge that I'm doing a lot here. I think if you separate the ring from the problems you have with the family, future rings quote will be handled better based or you won't have as many first calls. And I don't think you need to throw your brother under the bus who was really nice and was like, hey, it's a little too soon. Let's, let's not do anything too much. So that's my feedback. I mean, when you say the fact that I'm not in a rush to get married, you've made it a very personal thing like that. I, that's what your, your email reads. I'm not in a rush to get married and have not chosen to have kids apparently means I don't deserve piece of our grandmother's legacy you have taken, hey, let's whack up the ring to a different place. That's my feedback to you. You took, hey, we got this great family heirloom. I want you to have this and you to have that. And you're like, oh, cuz I don't want to have kids. You don't think I deserve the whole ring. And it's like your family will be like, what the just happened. They're not going to get it. I think you need to understand that the bill you feel you have rung up with the family does not match the bill that the family has felt it's rung up with you. That's your issue. I feel like King Solomon today. That feels very. And that's my, that's, that's my, that's my take. I, I. You know, I don't mean to come back at you, but your last paragraph will not be taken. Your last paragraph doesn't win you anything. Let me read it again. Here's what's really eating at me. I'm the oldest daughter. I'm the one who gets called first when anything goes wrong. I hold everything together. Like, you sound like you're giving a villain speech. Like, here's what's really eating at me. I'm the oldest daughter and I'm the one who gets called food first when anything goes wrong. I hold everything together and somehow I still end up feeling like an afterthought while my brother waltzes in and gets to put on a pedestal for simply existing. Well, not anymore. It's Nancy's time and you're all gonna pay for it. You sound like the Wicked Witch of the West. The fact that I'm not in a rush to get married and have chosen not to have kids apparently means I don't deserve a piece of our grandmother's legacy. We've agreed to get the ring appraised and figured out from there, but I'm still not over it. I'll be getting you, my pretty. See how you sound? That was a dramatization. You don't sound like someone who can be negotiated with. Right. Sometimes you gotta just hear yourself. I'm just saying that route and you wrote it to a safe space that I just maybe made you feel bad. I don't mean that wasn't to make you feel bad. But that route that you took with me ain't gonna for the dad that you could tell got sad when you said, hey, I, I, I, I told my dad that I didn't. That didn't feel fair and I wanted the ring or at least the solitaire. My dad looks sad and hurt by my reaction. You got a puppy dog dad. Let me tell you. I hold everything together right away on your broom. I'm just saying. Just some gentle feedback. Go to your parents with how you feel that you are leaned on a lot by the family and that you're exhausted by it. And then let's figure out the ring differently. Jtrain podcast at gmail com jtrain podcast at gmail com Mailbag Monday. We're here every Monday. Keep sending your emails. Tell a friend back next week. Boom.
Episode Title: My Brother is Getting My Late-Grandmother's Ring! Help! – MONDAY MAILBAG
Air Date: May 25, 2026
Host: Jared Freid
This Mailbag Monday episode of The JTrain Podcast, hosted by comedian Jared Freid, focuses on listener questions centered around dating, relationships, family dilemmas, and post-grad problems. Jared, known for his candid, humorous, and sometimes tough-love approach, takes on three substantial listener emails in this episode, addressing topics like the complications of dating a family friend, navigating casual dating after widowhood, and the emotional fallout from a family heirloom dispute.
A woman shares the story of reconnecting and going on a magical, four-hour date with a family friend after he ended a long-term relationship. She wonders how to handle texting while he’s away for a 10-day family vacation and is nervous about getting invested too soon because of their interconnected families.
A 36-year-old widow, single after her husband passed four years ago (together since age 19), seeks advice on how to navigate returning to dating, specifically looking for something casual (not marriage/kids). She’s tried speed dating, unsure about dating apps, and wonders how and when to share her widow status.
A woman faces a family dilemma: her father suggests splitting their late grandmother's diamond ring between herself (the eldest daughter, child-free) and her brother (who wants to propose soon), giving him the center stone for his engagement and her the smaller diamonds. The emailer feels discarded and overlooked, fueling feelings about her family role as the “fixer” and afterthought.
“I think the ring… was the straw that broke the camel’s back for all these issues. The family calls you first—but doesn’t see it as labor. They’ll only understand if you actually tell them what you’re feeling.” (49:42)
Jared Freid is warm, energetic, and direct—mixing heartfelt compassion with sharp humor and “real talk.” He’s sensitive when needed (consoling the widow), but doesn’t shy from challenging listeners to see uncomfortable truths about themselves or their situations. He frequently uses exaggeration and playful dramatization to both lighten and spotlight the emotional stakes of each scenario.
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