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Jared Freed
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 mail bag Monday, where you, the listener, email me, the comedian with your questions, anything you'd like. You can send in anything you like. Friendship questions, relationship questions, anything family, anything. That's like a real specific story that you want to hear the feedback from someone who doesn't know you, where you can be anonymous so you can hear an honest answer. That's the problem with advice from friends. And they know you and they have already built all of their biases. Is it biases or biases? Whatever it is, they know you from college and they go, well, you got drunk that one time, so you're probably doing this or that. I come here just with what you write to me in the email, and I'm going to give you a perspective. It's going to be honest, it's going to be thoughtful, it's going to be kind. It's also going to be real. I hate those people. I'm gonna be real. I, you know, I'm not saying as a brat, anyone would. It's easier here from my computer at the beach, baby. Listen, want to thank you for being a Listener. It's week two of the year. We're in 2026. It's happening. Thank you, thank you, thank you. We're gonna get right into it. I got three emails from listeners. I want your emails. Jtrain podcast gmail.com jtrain podcast gmail.com Also, you can follow the Instagram account at J Train Podcast. Jared, Saw your show with my family in Florida over Thanksgiving, and my dad loved it. Thank you. On to my dilemma. I hope they liked it, too. Just the dad. Okay. The dad was like, it was great. Everyone else is like, no, it's a good show. On the subject of shows, I am going to be in Tampa, Florida. Atlanta, Georgia, Charleston, South Carolina. Beach Mountain, North Carolina. Boston. We added a second show. First one is sold out. Dallas, Houston, New York. We're adding a second show first sold out. Toronto, Vancouver, Seattle, Tempe. Always more dates getting added, but those are the ones I have. Jared free.com come to the show. We got a good show. So it's a. It's a fun show. I just did San Diego Shout out to Mic Drop Comedy club in San Diego. Fantastic club. I loved Everyone who worked there, they, they, you know, sometimes you go to a comedy club and they take care of you. I felt taken care of. It really was nice. So let's get into the show. Come to a show. Let's listen to the show, share the show, and thank you for being a listener. All that good stuff. Okay, on to this person whose dad liked my show in Florida during Thanksgiving.
Co-host or Guest
A jury is still out on whether.
Jared Freed
They like the show, but they are writing here, so I'll take it. I'll assume the best and think that they had a great time but were worried about their dad. And then the dad was like, he's pretty good. And now they feel relieved and now they're writing into me. On to my dilemma. I went on six dates with a guy, overall pretty good. You know, I'm just gonna say if I go on six dates with someone and my review is pretty good, I don't know what I'm doing there at this age. I think age comes into this, you know, at 40, with my life set up and things are good. Why do I, am I, am I here single today for Pretty Good? And what sucks about this conversation is that it becomes some sort of me getting to judge the other party and it gets personal and it sounds mean. It's not mean. This is about the match, not you versus them. Is it, Is this we spectacular. There's a lot of people in couples that I would not want to be a part of at all. And in their world, in their bubble, they are in love and enjoying and they are having the time of their life. And I am happy for them. I'm jealous of them, I'm envious of them. But that doesn't mean everyone is a match in that way. So pretty Good is to me, over. You know, when you say I went on six day, I can answer your email now. It's a longer email. We're going to get into it. But I mean, to me, if someone, if my best friend came up to me and said, I went on six dates with this guy, overall pretty good, I would go, is that the life? Is that kind of where, you know, if we get 10% better than, oh, pretty good, is that the life you Want to live? 10% is a lot of movement. If you do in the market, if you make 10% on your money, you've had a great year, do you think it's going to get 25? Like, if we put this in numbers, it gets less personal and it makes the decision easier. If this got 10% better, would I Be with the love of my life in a life that I would hope for and want for any of my loved ones. Probably not end it. There's your answer. Next. No, I'm kidding. So let's get to their email. But maybe that's the pep talk you needed, because sometimes this feels like, you know, I have this, where I'm like, who am I to say that these dates weren't enough for me to go to the next level?
Co-host or Guest
Let me get to their email.
Jared Freed
But overall, pretty good. But there were a few moments I just should. I just couldn't shake. First time we hooked up, he went at it like a bunny rabbit that just drank a Red Bull. I tried to let it go. I mean, of the reasons to, like, not keep going, the sexual stuff to me is, like, stuff you can work through with someone you love and that you're excited about, and then you go, oh, they're doing the bunny rabbit. Okay, I can have a talk with them. Like, to me, now you're just making fun of someone you really don't like. And I'm not saying you're being mean. I'm just saying that's why, like, if you did this on stage, maybe your friends would laugh hysterically and the audience would be like, oh, then just don't go out with him anymore.
Co-host or Guest
Why are you telling us about this?
Jared Freed
All right, then I took him to my friend's Hanukkah party. Instead of grabbing food like an adult, he leaned over and whispered to me, can you go get me a latke.
Co-host or Guest
And put it on your plate?
Jared Freed
Immediately, I was icked out. Just get your own food. That, to me, is worse than the bunny rabbit fucking. Like the jackhammer thrusting. I'm fine. We can. Hey, I like it a certain way. What do you like? What do I like? There's a negotiation.
Audience Member or Friend
Can you get me the lake over there? I just don't want to make a. I don't. I don't want to make a fuss, and I don't know anybody here. Yeah, just go grab me the lock. You put a little sour cream on the side. No, I don't like applesauce. I like to keep my sweet sweet. My savory savory. Yeah, but just go over there, because I don't want to, like, walk up in front of everybody, and it's a little embarrassing. Like, what if everyone knows that I'm eating food right now? Yeah, I. I just. You know, I want to save all my energy for all the jackhammer sex that we're gonna have later. Yeah, yeah, yeah. When so just one locky.
Jared Freed
Listen, I guess a single locky would be more the most annoying part. Yeah, I, I and this lands in the like, you know, the ick is really women wanting to be treated in an old school womanly way by a man who's strong and gets what he wants. You know, like all that stuff that people will deny like, exists, but it's a know. So him going, can you get me a loy?
Audience Member or Friend
Yeah, just go across the room. Yeah, yeah, yeah. No, make sure it's the one that's a little bit more fried than the others. I like them a little well done. Yeah, yeah, yeah. Just get the well done, Locky. One single Locky. A dab of sour cream and then on your way back, just put it on the table and look away so that nobody sees that I'm the one you got it for. Okay.
Co-host or Guest
Yeah.
Audience Member or Friend
Thanks. I'll see you later.
Jared Freed
That would be. Yeah, I'm turned off by the act out. I, I get it. I, I mean, to me, this is over. Next, a hockey game date.
Co-host or Guest
He asked if $60 ticket for a.
Jared Freed
Next we planned a hockey game date. He asked if $60 for a ticket was okay. That alone gave me pause. Yeah, well, if they're asking you if the amount's okay, you are paying. I guess I expected him to just get the tickets and let me grab drinks or food. That's how you would want it. That's the fun way where he says, even if she doesn't get the food.
Co-host or Guest
Or drinks, we're good.
Jared Freed
You know, the expectation is, I'm taking you to the game. Hey, let's go to the game. Is I'm taking you to the game. He's saying, hey, so if you wanted to do a hockey game, if I get the $60 ticket, is that cool with you? Is, are we on the same page financially with this ticket decision? Yeah, it's not sexy. Make it feel like a date, you know? Then the day of the game, he texts me this, I'm about to buy my ticket. Want me to get yours too? Oh, he is like making sure something.
Co-host or Guest
About that absolutely sent me.
Jared Freed
I wouldn't even say that to a friend. We just the tickets in Venmo at the game. I was said I was at the game. I said I was thirsty. He told me to use the water fountain. I bought my own water. Later, I was hungry, so he bought a hot dog and we shared a hot dog. You shared a hot dog? She writes, oy, yeah. You don't like him. It's okay. There's not much he can do at this point. It's over. Share a hot dog. What? Like, lady and the. You get one side, I get the other. Do you bite from the same side? I guess you do. But even that, there's some foods, when you share them, if you think too much about it, you go, uh, yeah, I don't know. Like, try and share soup with someone. Some. If you think about soup for too long, you're not sharing soup. I share soup with family, but we gotta, like, share DNA or some shit. I ended things a few days later over text. My question is, was I being too picky? No, you weren't. You didn't like him to be. The. The reasons make you too picky. The. I. I just don't see where a match doesn't make you a picky person. Should I have communicated how these things made me feel? No, they are him. That's it. Or is this just a classic case of listening to the ick and moving on context? After I ended, he asked if anything, if I. After I ended, he asked if any he did anything wrong. I said he didn't. He said he would hang out with me if my feelings changed because he really enjoyed spending time with me.
Co-host or Guest
Thanks a girl who wants her own hot dog.
Jared Freed
Yeah, this is one of those things. I think you did it right. I mean, you wrote into a podcast with the specifics, like, the specifics you gave to us. And I'm, like, appreciative that you did, and I am. This is an email that I would ask for from any listener, you know, but us kids are here having fun. Like, I. I think, like, if he was like, is there anything I did wrong? And then you sent him this. This podcast episode, I would actually, as much as I want you to share this show, I would tell you, don't do that. This is a conversation had amongst friends where you have a little laugh and then you go. And then you end it by going, he's just not my match. This is just not for me. And the minute you go into, am I being too picky? Well, if you said if everything was amazing and you really love this guy and you go, but he bought a hot dog and said we could share it, I would go, yeah, you're being too picky, because that. Here. Here's the thing about, like, what do I end it? Do I not? And I go through this myself, and it. Listen, I'm. I'm sitting here answering this, but it is much as much my problem as it is yours. Where I. You. And I'll speak from my own personal.
Co-host or Guest
Experience so that you can take away from that what you will.
Jared Freed
You get into this mode where you go, who am I to end this with this really nice person who's just trying their best, and you start to get down on yourself and you think, and you know they're going to be okay without you. Of course they are, because you're fine and they're fine. It's. It's the match you're looking for. You know, at this point, I'm just repeating myself because I do think, you know, like, you know, the idea of asking yourself, too picky, not too picky. It's going forward in a relationship is like a mathematical equation too. Like I said before, can this get 10% better? To me, you go on six dates, and if you're still thinking about the hot dog, then the relationship, the interpersonal thing, wasn't so extraordinary to make you not think about the hot dog. There it is. Not too picky. Good luck. And it sucks because you go, I got someone. I, you know, they're trusting and they're nice and there's so much other horrors out there that why don't I just know with what I got? I think you move on. You've already. I. I don't think you're. There's not, there's nothing to question other than, you know, the one thing I would question is how honest am I being on the dates? This guy, you know, let's. Actually, now that I think about it, this guy is being his whole self. I don't want to pay for the ticket. You're going to pay for yours. I'm going to pay for mine. Let's go to the game. If anything, you can learn from this guy that he owned who he was. I'm a guy who takes a girl to a game and we split the tickets. Let's respect that. You are someone who laughed along even though you didn't think it was so fun or funny. Maybe this whole thing is a lesson for you to be a little bit more you when you're dating you six dates in, and he has no idea that you were a little turned off along the way. Hey, you're humping me too quick and fast. I'm not a. I'm not a piece of wood you're hammering. You know, I think that conversation could have happened. You're. You were intimate enough to be intimate, but not intimate enough again, like, these are easier said than done. But I think if you're going to Have a takeaway. It's let's fail quicker. J train podcast gmail.com j train podcastmail.com I'm on the road. We read the road dates because you said your, your, your dad loved it.
Co-host or Guest
And then I went into it.
Jared Freed
Come to a show. Come to a show. Come to a show. Come to a show. Bring your friends. Boston, New York. We're adding a second show. I'm taking a chance. I've gotten enough messages, we got enough time. Get the tickets. Now. If you're looking at my calendar and you see a date and you're like, we'll probably go, that's if you want to like support the show, that's supportive. We have a sponsor. Every plate Keep meals easy in 2026 with every plate. Every plate gets you restaurant level deliciousness every week. All in the comfort of your own home. Every plate offers tons of flexibility and a great rotation. Amazing meals with affordable meal kits to simplify your day. Every plate now has their biggest menu yet with options like Crispy Buffalo Crispy Buffalo ranch chicken and caramelized onion smash burgers. I gotta say, if you're looking to start your new year right, I'm always looking for a refresh. These meal kits, these meal plans, these, first of all, they're economical. It's hard to shop for. One, you end up wasting a lot. Two, they're going to apportion it right for you, so they're going to send you the right amount of ingredients you're not going to waste and then you're going to portion it right and you're going to get options. Crispy Buffalo chicken. Crispy Buffalo ranch chicken. You are not even close to making.
Co-host or Guest
That at home for yourself.
Jared Freed
And you got a couple moves. You got like grilled chicken. You do different sauces, but then you get tired of it and you end up spending more and eating more than you'd like. You'll spend less on every plate meals than you would on groceries or at a restaurant. Try every plate and pay just $2.99 per meal on your first box, plus free steak for a month. Are you kidding? Go to everyplate.com podcast. Use code J Train steak to claim your offer. That's code J Train steak at every plate.com podcast to get $2.99 per meal on your first box plus free for a month. Offer varies by plan. One free 10 ounces serving of steak per box for four weeks with active subscription. Ditch the dinner time dilemmas with every plate. Okay? I love that sponsor. What a helpful new Year sponsor I we got two more emails. Jared, I hope you're hanging out with your girlfriend. And they write in parentheses cell phone after a great show. That's what I do. After a show. I sit on my phone and I ooze. I hope you're in the mood to help a fan out with some dating advice. I am on this show. You write in here. I'll get back to you. Let's do it. Because I don't have enough time to wait for an email. Read on you up episode and I find myself in the need of the wisdom of Papa J. Papa J.T. listen, I'm here for you. J train right in. I started dating the sweetest, kindest man in the world about a month ago. I'm going to guess I haven't read this. They don't like them that they are mad at themselves for not when you call someone the sweetest, kindest man that is 10 minutes from someone getting dumped. They're the sweetest, kindest person. Sweetest and kindest. I know bad news is coming and especially on a fix up, you have to meet my friend. They're the sweetest kindness and I'm like, I don't want to meet him.
Co-host or Guest
I already can tell.
Jared Freed
No, I want pain in the ass like opinionated asshole. That's what I want. Yeah, I'll introduce you to my friend. But they're like, they're a lot. Bring that on. They're a lot but they know what they want. Kind of sweetest. That's usually someone who doesn't have an opinion on anything. I need opinions. But let's see if they're going to dump this this sweetie. I started dating the the sweetest, kindest man in the world about a month ago and it was a welcome change following a really crappy marriage.
Co-host or Guest
Well, I'm sorry to hear that.
Jared Freed
So I got in too deep too quick. I got in deep too quickly. We were going on our first trip away tomorrow and I've already realized we're not compatible. I mean I'm looking at the camera. I just gave a Jim Halpert at the camera. I told you. Yeah, I and I get it. Post marriage you're used to relationship interactions and then you get out of the relationship and now you're a house cat out in the wild and you got too far along and I get it. So they write we are going on our first trip away tomorrow and I've already realized we're not compatible. I. E. Your girl got the ick.
Co-host or Guest
And now I don't Know how I should behave this weekend.
Jared Freed
He's a had a. He's had a really awful rough year. It's about to get worse. So I'm trying to tread lightly with.
Co-host or Guest
As little hurt as possible.
Jared Freed
Should I a, show him an amazing.
Co-host or Guest
Weekend and be as loving as he.
Jared Freed
Wants to me, wants me to be.
Co-host or Guest
So I can make the weekend as wonderful as he thinks and hopes it.
Jared Freed
Is going to be? No, no, no, no, no, no, no, no, no. Stop it.
Co-host or Guest
End it.
Jared Freed
B. Start withdrawing.
Co-host or Guest
Grow colder now. So he isn't surprised when it.
Jared Freed
When I ended soon. You got to end it before you go. On one hand, I don't want to give mixed signals. You already are. But on the other hand, I do want to boost his spirits. No, nobody's spirits are boosted by the person who's going to dump them. And especially afterwards, you start to think back. You're like, man, was that all a lie. So you feel even more delusional. And I've done this. I've been you. I'm not saying I'm above you. Believe me. This is a tale as old as time to me.
Co-host or Guest
I'm just.
Jared Freed
And this is the hard part about getting older and being single is you're almost too aware. So you become. You start to get scars from stuff like this. Like, and I've been there where I'm like, I know I want to end it. Should I be nice and try and ease them off to see or do I just shove the boat off the marina? But on the other hand, I do want to boost his spirits and show him some light and beautiful time. No, he doesn't want light and beautiful time with someone who doesn't want to be with them. I'm just torn and needing to know.
Co-host or Guest
What the good word is. Haha. Keep doing the Lord's work. Thanks for even acknowledging me. You're the best person to be a.
Jared Freed
Fan of since we all know you read all your messages. Yeah, I read them all. I'm happy you wrote in here.
Co-host or Guest
You have to end it. Don't go on the trip if you've.
Jared Freed
Already gone on the trip. You gotta end it. It's over, you know, and it's like, this is the problem, you know, the ick has turned into since I did.
Co-host or Guest
The bit on the special.
Jared Freed
I was working on that bit two years before the special came out and it wasn't what it's kind of turned into today. Now it's like this just catch all excuse and it's like. And it's an excuse for our own insecurities we are too insecure to say, hey, I don't want to be with.
Co-host or Guest
This person because I don't see a future with them.
Jared Freed
That's okay. And I get why we're insecure. We. I say we because I'm insecure. I'm too insecure to say that. Who am I again? This is the first email again. If I'm you, you have this trip. I mean, here's what I would also say to you some. Sometimes you're getting an answer to something you're not asking about. So I'm trying to tread lightly with as little hurt as possible. Should I, A, show him an amazing weekend and be as loving as he wants to be so I can make the weekend as wonderful as he thinks and Slash hopes it's going to be, or B, start withdrawing, growing colder now, so he isn't surprised when I end it soon? On one hand, I don't want to give mixed signals, but on the other hand, I do want to boost his spirits and show him some light. Slash a beautiful time. Here's my advice. Stop saying shit like that. That's annoying. I want to boost his spirits. You two are two human beings on this rock that's spinning in space. You're not better than him. You're not worse than him. You're just trying to get yourself to where you're trying to go, and he's trying to get himself to where he's trying to go. Sometimes those two paths intersect and you guys are on the same page, and you go. You both want to go to the same place, which is a loving marriage. That ain't the case here. So stop talking down about him. He's fine. You said he's had a tough year and a half. She wrote.
Co-host or Guest
I missed that.
Jared Freed
He's had a really tough, awful year and a half. He's going to be okay. He's human. He'll be her. He's gotten this far. He's going to keep going. He's not going to just lie on the ground and go, it's over. I need to give up. He's not going to do that. So you need to stop talking to someone like they're a child. And you need to say, hey, I've had a really great time with you. This trip we have coming up, it's just not going to happen for me. I am not in this relationship for the long haul. And for me, at this age, I need to move on from that. I'm not going to waste anyone's time, especially my own. Jtrain podcast gmail.com, jtrain podcastmail.com One more email with screenshots. We love a screenshot email that just gives us more of the flavor. Lets me taste it. J Train Huge fan of the podcast. I've met you after shows in New York City and Chicago and my sister and I were in tears laughing at your last Chicago show. Thank you. I love that Chicago show. I'm dealing with a slightly alarming situation.
Co-host or Guest
And could use your advice.
Jared Freed
Okay, Trigger Warning. I don't know what this is about. I haven't gotten through it. I just see screenshots. So alarming alarms me.
Co-host or Guest
I had been dating my now ex boyfriend for five years. We're both 29.
Jared Freed
Less than two weeks ago we had an argument over the phone that I.
Co-host or Guest
Believed led us to a Less than.
Jared Freed
Two weeks ago we had an argument over the phone that I believe led Less than two weeks ago we had an argument over the phone that I believed led to us taking space, not breaking up.
Co-host or Guest
I checked in once or twice, but otherwise gave him room. During that time he publicly announced a new girlfriend, all within two weeks and without any in person or formal breakup conversation. I was left confused and answering questions from friends and family who had just spent Thanksgiving with us. Many of them were shocked as most of us didn't even realize we had broken up. He's struggling with mental illness for years, which I always knew could complicate a long term future, but we had been in a good place recently. Since then, he sent aggressive, unstable texts calling me delusional, claiming he's rallying his troops, taking no responsibility, taking no accountability, and insisting how happy he is now. I've attached examples for Tom how does someone meet, date and make things official within nine days of ending a five year relationship? I don't believe there was overlap, but this is is is this not is I don't believe there was overlap, but is this not a massive red flag for both of them? Would love your take. Thanks for all you do.
Jared Freed
I so before I say anything, I'm going to talk to you, the emailer, because I, I I just want to be sure that you're doing take care.
Co-host or Guest
Of yourself, take care of your safety.
Jared Freed
Tell friends and family I'm not a professional, I'm just a guy talking out.
Co-host or Guest
Of his ass on a podcast.
Jared Freed
So I'm going to read the email.
Co-host or Guest
The text as you said to get tone.
Jared Freed
I don't think the texts are going.
Co-host or Guest
To matter is my opinion.
Jared Freed
Again, just one guy's opinion. I have an opinion on Your email.
Co-host or Guest
But I'll get to the text first.
Jared Freed
But let me just say, please take care of your safety and talk to friends and family about this. Don't hide this.
Co-host or Guest
That you.
Jared Freed
To me, that's a just the hiding. I know it's embarrassing. I know a relationship ended. And just make sure you talk to people, especially professional.
Co-host or Guest
And I'm not that. So let me just make sure I say that. So here are the text between them. She wrote, I came home last night to my phone blowing up with dozens of texts that I haven't seen, that I hadn't even seen. So don't make me the bad guy. I had no idea anyone was going to message you.
Jared Freed
It's not like you gave me a.
Co-host or Guest
Lot of time to tell people. What was it, a couple days? Literally hadn't spoken in over two weeks. If we were together, he writes, we would have at least checked on each other. You're delusional. Please stop this. I'm happy. Finally. I'm not delusional. I genuinely cared about you and I'm worried about you. I'm not trying to make this more difficult than it needs to be. I was just trying to tell you my side. He writes, I'm happy. The messages need to stop. Please stop. We are done. Yes, you've made that very clear. Thank you. I don't know who's sending the messages or what they're saying. Everyone that asks, I tell them not to not to. So please stop turning me into the villain. He writes, stop pretending like you don't know what you're doing.
Jared Freed
Bye.
Co-host or Guest
She writes, I honestly don't Laughing face emoji. I don't want anything to do with this. I'm just trying to find some peace. You clearly have a lot going on. If you want to have an adult conversation, let me know. Otherwise, I hope you take care of yourself. He writes. So I'm guessing you were embarrassed that I broke up with you again and didn't tell your friends and family. I get it's quick.
Jared Freed
I get it. It's quick.
Co-host or Guest
Bounce back. But we are done. But we were done. The messages I keep getting in my DMs are insane. Haha. So petty in such high school drama. Don't worry, I'm rallying my troops too. Okay? This is all very sad to me. Like I don't find any fun in this. And then she writes, I hadn't spoken to my friends and family about us because I was still processing and didn't know where we stood when we spoke on the phone. I Didn' not understand it. Was it as a clean final breakup. I thought you needed some space and that we would talk in person once emotion settled. I literally said we can have a face to face conversation about this. And you said you were checked out and needed some space. That's why I checked in. If I had understood it as final, I wouldn't have sent that text last Friday. And maybe that's my bad, but I clearly had still cared and didn't interpret it as the door being fully closed. Okay, it. So those are the texts.
Jared Freed
It seems to me, based on what I have here, that he posted about a new girlfriend and then he started getting DMS from your friends and family calling him out on that because you guys weren't fully ended as you sought to be fed.
Co-host or Guest
That's me.
Jared Freed
That's. I can, I can understand in a world how this is all happening. Okay, that sucks. Let me start with that sucks to have someone end something with you and have it be vague and not really ended. And then they all of a sudden are posting on social media with a new girlfriend. I would be angry, mad, upset, hurt, all of those things. I will say this. The. The, the way you write the email, I think you have to change your perspective. That's. This is my opinion based on everything I just said and this text. And it sounds like you do it a little in the text. And I'm just saying I can only speak to you. The emailer, he struggled with mental illness for years, which I always knew could.
Co-host or Guest
Complicate a long term future. But we, but we had been in.
Jared Freed
A good place recently. Since then he sent aggressive claiming he's rallying the troops.
Co-host or Guest
I've attached to that.
Jared Freed
How does someone meet, date and make things official within nine days of ending.
Co-host or Guest
A five year relationship?
Jared Freed
That is not your problem right now. I don't believe there was overlap, but this was not a ma. But is this not a massive red flag for both of them? I don't know why you're asking about them and their relationship that. Thank God you're not. If I was in a relationship with some. Listen, if you were his new girlfriend, writing in that is a different story. You and him are over. Obviously your concern is really about. It seems as though the concern from your end and this happens a lot after a relationship is with the news, with the pr, with the brand of this. Because you're getting questions. He just spent Thanksgiving with you. That's a big show of love and who we are and we are a couple and then all of a sudden he's gone. And now you're getting the question, and now you're looking for me to tell you, yes, this is awful. This is crazy. That he'd be with someone two weeks later. That doesn't help you. Yeah, of course I agree with you that all of a sudden being with your new girlfriend on Instagram is crazy. Again, that doesn't help you. Your problems are getting healed from this relationship, figuring out how you can be better in a relationship and owning your standards and knowing what you like and knowing that this thing was never going to work out. You got to be on the you train. Right now you're sitting on the sidelines watching him, looking for people to go, isn't he awful? What's that going to do for you? Nothing. Like. And. And that's what happens when you go. When it. When someone says I, you know, again, there's three sides to every story. He believed you were broken up. You believe you were on a break. The truth is somewhere in the middle. I'm willing to believe your side of the truth a little bit more based on how he's acted afterwards and you saying that he has mental illness issues. But I will say based on the tone of your email. And do you think they, they, they. I think you're concentrating on maybe the wrong things. You got to concentrate on yourself, me, myself and I instead of. Well, you know, because when. Usually when someone's worried about the outside world and how everyone's gonna see it and how embarrassing it's gonna be, that that's when people start not hearing the heart, the hard parts. That's sometimes when someone stops hearing we're broken up. I'm not saying he definitely broke up with you, that it was so ironclad from his point of view. I am just saying I thought we were on a break. And then he says we didn't talk for two weeks. I'm just saying there's. We're. I'm trying to get into you. I'm him. He is not who I am concerned with. Because even your just your question alone tells me your perspective is missing. Do I don't believe the. But is this not a massive red flag for both of them yet that's who you're asking about. Boy, that's crazy, right? What are you, your friends and family. We're all going to say, yeah, of course we're going to say yes, but you're still sitting here with an axe that you, you know, you're looking for answers from that you're never going to get it from. So I, I, I think you got to hang with your family and friends. I think you need to dump him. I know it's already been over. I think you need to say your final piece to him so you can get out of your system and let him know that you're moving on. And please do not text me again. I'm going to unfollow, unsubscribe. You have to unfollow on every social media. You got to get away from this person and start healing. You got to start thinking to yourself right now, you're so caught up, up with how you look that you don't really care about how you feel. And I know that's hard, but nobody really gives a shit. Nobody cares that, you know, the, the relationship ends. They just want you happy. So you're concerned with things that are not important in my opinion. So again, I had to get there because I do, I hope you heard how much I do know this. Yes, it sucks now. What? Yes, it sucks. He was at your Thanksgiving and now he's making out at Niagara Falls with his new, soon to be, you know, marriage. You know, to me, thank God I'm not in that picture two weeks after being at someone else's Thanksgiving. I wish her the best. I hope she, I hope that, I hope they are in a different world than we were. When you write you've been with your boyfriend five years and it, and it and you're left confused. You know, five years, a long time. Let's fail quicker. This is done. The relationship was a failure. You are not a failure. That's. We got to concentrate on you. JTrain podcastmail.com every Monday. Keep sending your emails back next week. Boom.
Host: Jared Freid
Date: January 12, 2026
In this episode of the JTrain Podcast, Jared Freid tackles a fresh batch of listener emails on the classic Mailbag Monday. Recorded from Delray Beach, Florida, Jared answers questions about whether to continue dating "really nice" people who just aren't a match, explores the "ick" factor in dating, discusses navigating awkward breakups, and gives insight on self-respect and honesty in relationships. Judgement-free advice, relatable stories, and a healthy dose of humor come together to create a supportive sounding board for all things love and modern dating.
“To me, if someone—if my best friend came up to me and said, 'I went on six dates with this guy, overall pretty good,' I would go, is that the life you want to live?”
- Jared Freid, (04:11)
“This is about the match, not you versus them.”
- Jared Freid, (04:25)
“If they’re asking you if the amount’s okay, you are paying.”
- Jared Freid, (08:20)
"If you’re still thinking about the hot dog, then it wasn’t extraordinary enough to distract you from the hot dog. There it is. Not too picky. Good luck.”
- Jared Freid, (12:02)
“Nobody’s spirits are boosted by the person who’s going to dump them.”
- Jared Freid, (19:55)
Listener Story: After five years together, a couple has a phone argument, takes a break, and the boyfriend announces a new girlfriend within days—without clearly ending the previous relationship. Now there are angry texts and public confusion.
Jared’s Insight: This is messy and more about miscommunication (and perhaps mental health struggles), but the key is focusing on your own healing, not his narrative.
Memorable Quotes:
“You’re so caught up with how you look that you don’t really care about how you feel.”
- Jared Freid, (30:43)
“Let’s fail quicker. This relationship was a failure. You are not a failure.”
- Jared Freid, (33:20)
“If you make 10% on your money, you’ve had a great year. Do you think it’s gonna get 25? If we put this in numbers, it gets less personal and it makes the decision easier.”
- Jared Freid, (04:45)
“The minute you go into, ‘Am I being too picky?’... If everything was amazing and you really loved this guy and you go, ‘But he bought a hot dog and said we could share it,’ I would go, yeah, you’re being too picky. But that’s not what this is.”
- Jared Freid, (11:25)
“Maybe this whole thing is a lesson for you to be a little bit more you when you’re dating.”
- Jared Freid, (13:21)
“Stop talking to someone like they’re a child. You need to say, 'Hey, I’ve had a really great time with you. This trip we have coming up, it’s just not going to happen for me. I am not in this relationship for the long haul.'”
- Jared Freid, (23:20)
Jared consistently encourages honesty—for yourself and with others—and not to linger in relationships that lack excitement, connection, or authenticity, no matter how “nice” or “sweet” the other person might be. He underscores the importance of listening to your gut (the “ick”), failing fast, not worrying about seeming “picky,” and putting your feelings before outside narratives or concerns with how things look. The episode wraps up with a reminder: relationships are about the match, not the résumé, and self-respect is always the right decision.
To submit your dilemma:
Email jtrainpodcast@gmail.com or DM @jtrainpodcast on Instagram.