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Jared Freid
Hello and welcome to the UW Podcast. I'm Jared Free.
Jack Maloney
And I'm Jack Maloney.
Jared Freid
It is such a pleasure to be back here with you, Jack.
Jack Maloney
Thank you for having me back.
Jared Freid
I appreciate it. Listen, for everyone that has been listening, you know, it's Jordana Abraham Marinelli's maternity leave.
Sponsor/Ad Voice
We wish her the best.
Jared Freid
If you want to check in with Jordana, sign up for you up with benefits. You sign up, you get two extra podcasts a month. Jordan and I go over zoom. We're going to check in on her, the babies and all that stuff. So if you want an update from Jordana, go sign up for you up with benefits. We love doing those episodes. People really genuinely seem to like being a member of that subscription. We don't lose people, which means a lot to us. So go, go, go sign up. The link is in the bio. This episode. Jack, how are you? What's going on?
Jack Maloney
I'm doing great, Jared.
Jared Freid
You were on the show. You people loved.
Jack Maloney
You was on the show. It was so much fun.
Jared Freid
You were great.
Jack Maloney
This is so silly, Jared, but I always. This one line you just said, like a certain type way where you just go, I watch that clip all the time for no reason. I'm just like, the way Jared said that killed me.
Jared Freid
It was so funny.
Jack Maloney
I was like, that's the gay community in a nutshell.
Jared Freid
Only my new account, that's my new website where I put out my otter. You know, my otter, you know, pictures that I take.
Jack Maloney
I've been seeing that. I've been seeing that. But they're like otters only but you put little hats on them.
Jared Freid
Yeah. Love a little hat on an otter. Jack, what's going on in your dating life? When we last checked in, you were. You were like getting out there.
Jack Maloney
I was getting out there. I still am.
Jared Freid
Okay.
Jack Maloney
Yeah. But I think I. There's been some developments.
Jared Freid
Please.
Jack Maloney
So, like, I don't know, what was that a couple months ago? Three months ago.
Jared Freid
Three months ago, let's call it.
Jack Maloney
Yeah, it's been a minute. So yeah, I was really getting out there. And when I was last on I felt like I was really just trying to meet a lot of people. And now I would say I'm doing the same, but like with slightly more intention.
Jared Freid
Okay.
Jack Maloney
And like, so I kind of like kind of have a dichotomy in my dating life right now. I cannot lie. I have this one half of me that is like really dating with intention, like I'm looking for a boyfriend and then another half of me that's kind of just slutting it up if I'm being so honest.
Jared Freid
Well, I think this is where, you know, that's the, that's gay, straight, however you identify, that's like a man. Yeah, you know, like that's. This is where a lot of women get frustrated with men. It is because we have a mostly female, straight female audience, but we cater to all backgrounds. But for those women, they go, why would this guy say he wants a relationship? And now he's getting weird. And now because there is this like devil, you know, angel thing going on constantly.
Jack Maloney
And honestly, girls looking at you as a gay man, I can completely empathize with you because I deal with men, but as a man, I am a man. So I know how we think too.
Sponsor/Ad Voice
This is.
Jack Maloney
And I know I'm capable of the same evil.
Jared Freid
This is why I'm calmed by the gay community. Right? You know, like I me, yeah, I feel better cuz I feel crazy. You know, I'm like, wait a minute, I do. And then you hear from a guy who goes, listen, I, I kind of op. I'm operating the same as you with men and then I'm dealing with men in the same way that you're. That is, you know, not personal. I think like the fear with dating and I think most people don't want to be evil.
Jack Maloney
I completely agree. And I would say honestly, the homosexual dating patterns for both lesbians and gay men offer a really clear microcosmic example of the problems of women and the problems of men. Okay, I'll start with the problems of men, cuz I am one. We have this dichotomy. I want a serious relationship, but I kind of also want to get laid. And I'm always looking for both of those things, right? And sometimes they're with different people. And like sometimes I feel like a shitty person cuz I'm like, I'm on this date with you, but now I'm really thinking about having sex with you. Then you have a lot of my lesbian friends who are like, we meet for a week and then they want to move in together in a month. So it's like the emotions and the emotionality is. Is doubled. And with gay men and gay women, you have men squared or women squared.
Jared Freid
Right.
Jack Maloney
So it's like I always say, I truly think men and women balance each other very well.
Jared Freid
It's an interesting force.
Jack Maloney
Women force men to be more emotionally intelligent, more like connected to like the. The humanistic part of the relationship.
Skims Sponsor Voice
Right.
Jack Maloney
And I also think men can sometimes bring girls out of their shell a little bit, force them to maybe have a little more fun. I don't know, chill on it a
Jared Freid
little bit, Take some time. Let's have some fun.
Cozy Caravan Sponsor Voice
Exactly.
Jack Maloney
And that's not always a rule.
Jared Freid
Right.
Jack Maloney
Girls can, can get a guy to chill and a guy can be. Get a girl to be more humanistic, etc, but like when you have two men or two women, it's like you have the patterns of the sexes squared.
Jared Freid
That's so you really see that way to put it. So we're gonna do some emails here. We got a nick ear. Picky. We have. Jack is here. Jack Maloney is here. Go follow Jack. You've seen him on all the betches content. He's killing it. Hilarious. Does stuff on his own. So you want to go follow Jack Maloney. And he's also doing betches video club. It's a podcast where they basically go down nostalgia road and check out some old movies and TV shows and then have it out. I think that's a great idea for a show at the Jack Maloney. Let's do an ickier pick. You ready?
Jack Maloney
All right, let's do.
Jared Freid
So we know the game here. Icky or picky? You're dating someone, one thing happens. You're like, is it a valid ick or are you being picky? Dear J and J Medium time listener, hoping one day to be a longtime listener. Love the pot. I'm 31, female, recently reconnected with a guy from college. We had a really great first date. Easy chemistry, great conversation and quick goodnight kiss. I was feeling optimistic. So second date, not so optimistic. We had a good time, but wow. Our kissing styles did not mesh. He was very aggressive with a stiff and too plentiful tongue. And his attempt at second base felt eerily similar to a breast exam at the gym. So how would that be? Like, is he like clamping her titty yeah.
Jack Maloney
He must be, like, using, like, muff hands or something.
Skims Sponsor Voice
Like.
Jack Maloney
Right. Like medical. Medical hand.
Jared Freid
Right. Going real claw.
Sponsor/Ad Voice
Like.
Jack Maloney
Yeah, we're kind of. It's either. It's. I feel like it's either mittens or knives, you know, that's something that's, like, really unnatural, so. Right.
Jared Freid
Because I thought could be a snapper, but you think it's more of a cupping.
Jack Maloney
I think. I think it's probably a cupping because that would. That would be like a breast exam. Right.
Jared Freid
I would have to be deep in a relationship with someone where we were very comfortable with each other. But I'd like to feel what it feels like to cup. Right.
Jack Maloney
Like, what's the weight of that?
Jared Freid
Right. I just want to, like. And then they be like, what are you doing? I've had that with, like, my balls. Like, women will go, oh, I just want to, like, play and see what it is. And I'm like, oh, that's not. Yeah, yeah, go ahead.
Jack Maloney
I've had that with my balls, too. But it's less curious and more charged. Okay.
Jared Freid
It's a little more on the nose. So is this something you can be blunt about or is the only acceptable option to gently guide him in the moment with stuff like, I really like it when you. And even though everything I come up with sounds awkward or borderline rude, I've heard the advice to reinforce good behavior, but there was honestly nothing about the kiss that could be mistaken as good. I actually really like him, but I'm so turned off by the kissing that I don't think I can get past second base unless something changes. So icky or picky. He kissed like a medical professional looking for romance, not a medical exam. So have you dealt with this in your life? Have you ever been.
Jack Maloney
Yeah.
Jared Freid
Give me. Do you have an example of, like,
Jack Maloney
have a perfect example of a guy? Yeah, this was actually from a while ago, from high school. But I remember this guy was seeing super handsome, really into him, and I
Sponsor/Ad Voice
would assume high school.
Jack Maloney
We were high schoolers, you know?
Jared Freid
But I'm saying in high school, it's always awkward, but, like, of course you guys are both in high school dealing with your sexualities. It's a little bit like, who do you talk to? You know, who do you take examples from? There was no heated rivalry. You can't even, like, look to an example on tv.
Jack Maloney
Nope.
Jared Freid
I guess you got porn, we got porn. And that's it. That's kind of scary.
Jack Maloney
We had seancody.com which for the gays out there, I don't know it. Something. Yeah, you don't need to know it.
Jared Freid
Okay.
Jack Maloney
Don't worry. You don't need to know anything about that. How would you describe Sean Cody.com like a fraternity naked.
Jared Freid
Okay.
Jack Maloney
That's what it feels like.
Jared Freid
Okay. So.
Jack Maloney
Or go in the gym, undress all the guys and just have them keep doing what they're doing.
Jared Freid
Okay.
Jack Maloney
That's Sean Cody.com okay.
Jared Freid
But city.
Jack Maloney
So crazy, crazy, crazy place to be.
Jared Freid
I would say, though, this is jaredfreed.com for a very different, you know, thing going on. The tickets to my shows. Vancouver, Tempe. I'm gonna be in Seattle, so.
Jack Maloney
And if you really love Jared, you can also go to ottersonly.com where you can see otters and hats.
Sponsor/Ad Voice
Thank you.
Jared Freid
Hats. Otters with clams.
Jack Maloney
Yes. Otters. Otters. Otters.
Jared Freid
All otters.
Jack Maloney
Otters only.
Jared Freid
Otters only.
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Jack Maloney
I actually would say though, my experience with this guy was where I developed a very particular opinion about kissing. So he was so handsome. Whatever. We went on good dates and when I would kiss him, I felt like I was kissing a wall. Like there would be no tongue at all.
Jared Freid
Nothing.
Jack Maloney
It'd be like, it'd be like this, like just kind of like an old person with maybe no, no teeth or something. Like lips closed. I was like, we, we can employ a little tongue. And I would literally like, try to actually like aim my tongue into his mouth to be like, you got to open up, bro.
Jared Freid
You're trying to.
Jack Maloney
You.
Jared Freid
You're using the jaws of life to get the jaws out.
Jack Maloney
I was sort of doing what she's doing and trying him gently without being directly like, you're a horrible kisser. What's going on here? But here's the thing. My mom, when I was growing up, used to say something beautiful that I really love. She was like, relationships and dating are all about head and heart connection. You want to be with someone who your head and heart are in agreement with. Head being emotions. How do we connect? You know, do we have shared interests? Do we have good dates? Do we have chat? Heart is more passion. Sex, like physical chemistry. That's not everything, but it's half of the equation, right?
Jared Freid
Right. It doesn't have to be. It's not all head, all heart. You need a little bit of both.
Jack Maloney
You need both and they need to be in agreement. So to me, this sounds like a, a classic example of head loves it, heart doesn't love it.
Jared Freid
Does she give it another chance? Is this too icky to go back to? Do you you know, because she said it's one date and then second date. This is when the kissing problem. So you're on the second date. Like, I. I guess we go. We don't know.
Sponsor/Ad Voice
We.
Jared Freid
We don't know what happened from here.
Jack Maloney
Yeah.
Jared Freid
You get done with a second date and you've had a bad kiss with someone, do you give them another chance?
Jack Maloney
I would say yes. If this, if the dates were really good. Yes, I would give them another chance. And I think the instinct to guide them gently is. Is a good one. But I also think, you know, it depends on the context of intimacy. Right. If we're in the bedroom, I feel like you have more license to have conversations about what is occurring.
Sponsor/Ad Voice
Right.
Jared Freid
We got. We got feedback on that. That was negative.
Jack Maloney
Really?
Jared Freid
Herpes episode. And it might be different with the herpes episode. Well, not herpes, but like, STIs and testing.
Jack Maloney
Yeah.
Jared Freid
Have you that people said you don't do that in the bedroom. Because people might feel like they're being convinced. I guess this is different because it's like kissing. And maybe feedback could be easier because we're both being vulnerable. We're both in a state that.
Jack Maloney
I mean, do you not feel like when you're, like, in the, like in the situation of deep intimacy of, like, in the bedroom where you can kind of be like, ooh, actually, like, put your hand there. Oh, I like when you do this or just like, encourage this.
Jared Freid
You know, she said that there's nothing good to give a compliment on. And I think stuff. I think, let's wait on that. I think, let's wait. I think if I was on a second date with someone and we made out, I would assume the make out happened in a context matters. In a place that I would not normally make out.
Jack Maloney
Yeah, I agree.
Jared Freid
Street corner, car, restaurant, door, front. It's in a place that doesn't really make my kisses land the best.
Jack Maloney
Yes, I would agree with that.
Sponsor/Ad Voice
Like a.
Jared Freid
Like a show. Like if someone did a show at a bar, I would go, okay, I did my best considering the surroundings.
Jack Maloney
Right.
Jared Freid
So let's have some empathy for the venue that you had the first kiss. Let's just have empathy for you went for it. Like, let's be happy with the action that took place. You both were on the same page. Like, let's look for the. You were both having a good time. You were in the same universe as each other. You had fun, they had fun. Now let's give credit where it's due. You had the kiss.
Jack Maloney
Yeah.
Sponsor/Ad Voice
Okay.
Jared Freid
The kiss was Underwhelming. Yep. But great first date. Great second date. Until the kiss.
Jack Maloney
But here's the thing. I have to flag second base. Felt like a breast exam. That's tough.
Jared Freid
Right? And how are you and where are we.
Jack Maloney
Where are we having second base?
Jared Freid
Right.
Jack Maloney
Probably not the street corner. Probably not the concert. I would hope not.
Jared Freid
So maybe they were in a comfortable. They're in a venue where a titty
Sponsor/Ad Voice
grab could have happened.
Jack Maloney
Yeah, they're in a titty grab. Green zone. Let's call it somewhere more. Let's call it probably more semi private. Who knows? Maybe we got to an apartment. We don't know that. Or a house or whatever.
Jared Freid
We give it one more chance and
Jack Maloney
lean to Shaq, where you lean to all.
Jared Freid
All types of outdoor camping.
Jack Maloney
Yeah, of course.
Jared Freid
I think we give it one more chance.
Sponsor/Ad Voice
I don't think it's.
Jared Freid
I. I think it's a little picky to go. Great first date. The kiss was no good. I think it's a little picky.
Jack Maloney
I think.
Jared Freid
I think it's an. I think the second time around where. If you. If.
Sponsor/Ad Voice
If.
Jared Freid
Here's what I need to erase a bad kiss. Ick.
Jack Maloney
Let's hear it.
Jared Freid
I need them to respond positively and thoughtfully to me saying, slow down 100% slow down. Yep. Slow down is, like, not negative. It's not.
Sponsor/Ad Voice
It is a review.
Jared Freid
And it does help people reassess their timing.
Jack Maloney
Yes.
Jared Freid
So for a bad kisser who's coming at you with, you know, the hammer, tongue. Hey, slow down. The hammer down, like a whisper. Slow down. If. Because what they should say from slowdown is they should say, you take the lead. Let me. Let me follow you on this kissing journey. If they can't do that, then the ick is valid, because then if they. If they refuse to slow down and still try to lead, because if someone says it on to me, I'm gonna go. You're. You're the pacesetter now.
Jack Maloney
Yeah.
Jared Freid
That's the appropriate. To me. And again, this is all personal. This is my opinion. You might disagree. That's okay.
Jack Maloney
But this is.
Jared Freid
To me, slow down is just such a great way of giving a review that's not shaming them, but parenting.
Jack Maloney
Gentle parenting.
Sponsor/Ad Voice
Totally.
Jared Freid
And it's a way for them to go. For you to go, listen, I'm going to take the reins here. Yeah.
Jack Maloney
Now, this might be horrible advice, but maybe. And maybe this is because of my general sense of grandeur as a person.
Jared Freid
Okay. But I. I just want to go back for a second. That also doesn't help the titty grab.
Jack Maloney
I'm just saying the titty grab is.
Jared Freid
That's for kissing.
Jack Maloney
We're in a different. That's a different part of.
Jared Freid
We hope the slowdown lets them. Makes it so they rethink their grabbing of the titty.
Jack Maloney
Yeah. Cuz if we're kind of doing cup and cup and way, we don't want that.
Jared Freid
Oh, I've been wrong on everything. Let me unbutton the shirt. You guys take the. You take the. Okay, go ahead. I'm sorry.
Jack Maloney
No, I was just saying, I think, and this is probably just my general sense of gr. Grandeur and. And value of whimsy, but I like to sometimes in a sexual context or in intimacy, just, like, be like, okay, imagine if I was in a movie and I wanted this tape going because it's really good or because the date was really good, but it's not going the way I want it to. Like, how could I, like, keep the sparkle? How can I keep it cinematic but, like, direct him towards the way I want her to be? You know what I mean?
Jared Freid
So.
Jack Maloney
So how would I do it? I would stay in the zone of, like, sexy time. Like, maybe with tone of voice or like, and kind of be like, oh, like, really good when you do that. Oh, wait, maybe try this a little bit.
Jared Freid
Like, Right. You know what I mean? She's saying, I have nothing to say.
Sponsor/Ad Voice
Really good.
Jared Freid
I know.
Jack Maloney
And that's the tough part.
Jared Freid
I do understand. But yeah, yeah.
Jack Maloney
But I agree with you that we should have a third date. Because I think if this was. We had an okay date and the kissing sucked, I'd be like, all right, we're done. Bye. But if you're telling me we had a great day, great. We had a history.
Jared Freid
Except this.
Jack Maloney
Give it a shot. Maybe you need to reset the context. We don't know what the context of titty grab was. Where were we? So I would say maybe think about whatever, wherever that context was and try to make a better one for this next time and see if you can cinematically coach him.
Jared Freid
Right. So our advice for the icky or picky, we're saying it's a little picky, but with ick as an option.
Jack Maloney
Yeah.
Jared Freid
We're not saying it's not icky, but we're in picky land. On day two, everything's great, but a bad kiss and a weird titty grab. We're saying change the venue.
Sponsor/Ad Voice
Whisper your words.
Jared Freid
Yeah, and how about, let's see how they respond to a slowdown. Yeah, a slowdown.
Jack Maloney
Slowdown.
Jared Freid
I really think but I agree with you.
Jack Maloney
Let's get the venue to speed bumps ahead. Slow down.
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Alison Hammond
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Listener Voicemail
If the Featherington carriages are rocking, do
Jared Freid
not go a knocking.
Alison Hammond
It's a gala ball and you're all invited. Ta ra.
Sponsor/Ad Voice
We are pausing this episode with Jack because we have an exciting story that just came in and an exciting new sponsor. It's time for Smashing the Breakup, brought to you by Sonic. Sonic wants you to break up with your burger, the overpriced, low effort one that's been doing the bare minimum, and upgrade to their new All American Smashers Hand Smashed Angus Beef made to order classic toppings starting at six bucks. We have a voicemail from a listener who wants some honest advice on moving forward from a messy breakup, so let's go ahead and take a listen.
Listener Voicemail
Hi J and J. Looking for some outside perspective on a breakup that I went through recently. Maybe you can talk me out of doing something crazy. I broke with my last boyfriend not long after he lost his job. I know how that sounds, but I didn't break up with him because he got laid off. We were having some other problems in our relationship. And it was. It was just time. When we first broke up, it. I felt really awful about the timing of all of it because I've been laid off before and I know how terrible it feels to. Despite that, I thought we ended things in an okay place, but recently, one friend spilled that he has been talking to people in our circle, that I only ever wanted him for his money. It's just hilarious. I have my own money and that's not why we broke up. And he knows that if I was more spiteful, I would air out all of our dirty laundry from our relationship and make a big mess. But I don't want to do that. I just want to be chill and go our separate ways. I don't want to engage with his. But I also don't want people thinking I'm the villain here. I'm not a petty person, but I can go there if I need to. So how would you navigate this situation? Thanks for all that you do better than revenge.
Sponsor/Ad Voice
I love this because it's a tough one. Because the consequences of ending something with someone is that they have a story that people will agree with more than you. That's the consequence. You ended something for no reason at all. You had a good person that liked you, that wanted to be with you, that you were like, eh, I'm out. I can find better love somewhere else. Which I agree with you. It wasn't for you. It wasn't the match. That's okay. You're just gonna have trouble finding a lot of people who are gonna have fun with that conversation. Your story's not juicy. Yeah, it was a great relationship. They're a nice person, but I just had to move on from it. They lost their job, which was a little bit awkward, but I guess I'll have to deal with that. That's all your story is his story. When you're dumped, oh, you get a juicy one. What happened? I don't know. She just must have fell out of love with me. I just lost my job. Maybe she's more into me when I was making money than when I wasn't making money. Maybe that's all that mattered. Her he reality TV show episode that he can sit at the table and treat the brunch as if it's a campfire story. That is the pleasure of being dumped is that everyone gets to ooh and ah and you deserve better. And she can go screw herself. Fuck her. That is the unfairness of being the dumper. That's why I feel for the dumper. I am the dumper most of the time. So you have found a great place to complain to. As far as being seen as the villain, you're going to. I'm sorry to inform you that's going to happen for you. Someone's going to see you as the villain. There's nothing you can do about it. Meeting petty with petty will only get you more petty. Throwing gasoline at a fire will only make more fire. What I would do if I were you is I would shoot him a text. Hey, some things got back to me that made me feel really badly. I heard that you're telling people that I only wanted to date you for your money or for financial reasons. I want you to know that if it came off that way, I'm really sorry you felt that was why I was with you. That is not the truth. And I would really appreciate you not saying those things to other people because it really isn't my truth and it's unfair to me to be painted that way.
Jared Freid
That's all you have to do.
Sponsor/Ad Voice
You have to own it. You have to say, acknowledge that maybe they feel that way because it might feel that way from their end. You can't really deny that you can't tell someone how to feel. If I lost my job and someone dumped me within a month of me losing my job, that is something I could say if I felt my ego was bruised enough to say it. And that stinks for you because you have no control over the feelings that he's telling people. But you can say to him, hey, when you use my name, be a little bit more careful because it is getting back to me. So that's what you're letting him know. Hey, these things are getting back to me. I'm hearing about this. I want to let you know that that was not my intent. I can't convince you to feel a different way, but I'm letting you know these words are on paper. This is what I am trying to tell you is that it wasn't about that. But I can't control how you feel. But also, please saying that to other people because I'm hearing everything. And you think that you're being secretive and fun. You're not. And now you would hope he would feel bad. No one wants to be known as a shit talker. You would hope that he would take it back. The people he said it to will never unhear what they heard.
Listener Voicemail
He.
Sponsor/Ad Voice
But at least you have sent some sort of warning to let him know that his words are being heard. So I hope that helps You. I think you need to let go of this. I don't want to be the villain. You are. When you dump someone, you are. You are in a position of power. You are punching down. They're the loser. You're the winner. You're going to find hotter. He's going to find nothing. That's okay, but we're going to move on. You can send one text. One text. That's all for smashing the breakup. Thanks again to Sonic. Remember, breakups are about growth. And sometimes the best way to get over a breakup is by upgrading your standards, including your burger standards. Break up with your burger and try the Sonic $6 All American Smasher Meal instead.
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Jared Freid
And breathe.
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Listener Voicemail
Visit 1-800-contacts.com today to save on your first order.
Jack Maloney
1-800-contacts.
Jared Freid
Let's do another email. Uupetches.com Jack Maloney, you're killing it. This is the second time on the show.
Jack Maloney
Got it here. Also, I have to point out, we're still high. We're still J and J. J, we are still. We're still J.J. you don't even have to change.
Jared Freid
Keep it consistent.
Jack Maloney
You can keep that.
Jared Freid
I love it. All right, let's go. Let's do it. Do another email. Let's do. We got an advice email.
Jack Maloney
All right, you want me to read this one?
Jared Freid
Great. Go ahead.
Jack Maloney
Hi, J and J. NJ I am 24 and a trans woman, and I'm writing because I'm feeling really discouraged about dating and about not being seen as a real option. Recently, I was at dinner with friends and we were talking about this cute guy. Everyone kept saying how sweet he was and how they needed to find him a good girl to date. Half joking, I said something like, hey, I'm available and willing. And everyone laughed and kept going on about finding him a nice girl. I even doubled down and said, like, hello. And while I was joking, on the surface, it was very clear that no one actually saw me as a serious option. So, first of all, girl, hearts out to you. Hearts out.
Jared Freid
No, this sucks.
Jack Maloney
Yeah, this sucks. So let's see what. So let's sort of heighten it what made it hurt more is that I don't want to hide it. But it heightens, I fear. What made it hurt more is that these people are people I consider friends. They affirm my gender, use the right name, and call me a girl. But when it comes to real life dating, it feels like there is a disconnect. None of them would ever think to set me up with one of their straight friends. And it made me realize that being affirmed socially does not always mean being seen romantically. For context, I have not medically transitioned and I understand that might be part of it. I'm not expecting everyone to be attracted to me. But what hurts is the assumption that no straight guy ever would be simply attracted to me because I am not a CIS woman. It makes the dating pool feel incredibly small, makes me question if I'm being realistic or if I'm internalizing something that is not true. So my question is, how do you cope with feeling invisible or written off before you even get the chance? And how do you talk to friends about this without sounding accusatory or insecure? Thanks for reading and for everything you do. Complicated.
Jared Freid
I think this is complicated. This is very interesting.
Jack Maloney
It is very interesting. And I'm very curious, honestly, about your perspective as a straight man, because I feel like I have the queer eye in where I know so many trans girls and I'm. My absolute best friend in the world actually happens to be a trans girl. And it is a very, very, very, very challenging experience for dating. No, because you have gay men want to date men, straight men want to date women, and trans women are women, but are they women in the eyes of straight men because they were born male? So it's like, then they're thinking about, oh, well, do you still have a, you know.
Jared Freid
Well, let me start with your, your, your. You're bringing me into a world where I feel like I don't want to say the wrong things. You know what I mean? And I just want, like, please, if I make a wrong step, I'm giving you the permission to say, to treat me like a big dummy and tell me when I'm wrong, because. Will do. But this is also part of my answer, okay. Is that I think there's such, you know, like, again, what they're dealing with is friends who are somewhat being performative, in my opinion. Like their friends are saying all the right things. Again, in the way that I'm trying to say the right things. But what do they truly feel? And I'm sure she feels that and knows that from certain People, I'm sure there are friends she knows are like, we have this with comedy. Let me relate it to something.
Jack Maloney
Yeah.
Jared Freid
Relates that when I tell someone I'm a comedian, I know right away when they're, like, put off by that. Don't get it. And when they get it and when they're like wonderful people I want to confide in. I'm sure she has that, too. She has levels of feelings that no one can tell her how to feel when someone's like, oh, my God, you know, like they're talking about something or when they're. She said she's. They're using the right.
Sponsor/Ad Voice
Right terms.
Jared Freid
And it's like, using the right terms doesn't mean that they see you as the way that you want to be seen or asking them to see you. And this happens to everyone generally, like, that feels othered.
Jack Maloney
Yeah.
Jared Freid
You know, you're the. Again, like, I've. I've been the overweight friend. I've been, you know, the friend that goes.
Sponsor/Ad Voice
They go.
Jared Freid
They don't see you as the person they would fix up. I'm the funny friend. You know, this is again, like. And again, so, like. Like to make it so to kind of, like, normalize this, which is. I would assume what she wants.
Cozy Caravan Sponsor Voice
Yeah.
Jared Freid
Is to be just a part of the conversation.
Jack Maloney
Yes.
Jared Freid
I think it sucks because what her friends. And again, like, this is nothing about the prospective men as much as it is about her friends.
Cozy Caravan Sponsor Voice
Yeah.
Jared Freid
To me. Right.
Jack Maloney
And me, you know, like, obviously we don't know her friends. We don't know who they were talking about and how they're connected. But I completely agree with you. I mean, listen, from my own experience where I felt othered, I, you know, I definitely have been othered within the gay community before. The gay male community can be very harsh, very visual. It's men, right. So they're looking for a certain body type, a certain size, a certain something. And like, you know, there was a period of my life where I was overweight. And, like, that period proved a lot harder for me dating.
Jared Freid
Right. And it's also a lot of your own insecurities that you know, too, where you go, like, like. And again, like, when she hears everyone discussing this guy who's single, and then they don't bring her up as an option. She's saying it's because I'm a trans woman.
Jack Maloney
Yeah.
Jared Freid
It might be this guy likes certain types or has they know something about his dating history. Or it might be exactly what she thinks. We don't know. It might. Our Plight. My plight is with weight. And our plight is weight with. Or. Or comedian is not the same as hers.
Jack Maloney
Totally. We're just trying to 100 just like relating to the idea of other feeling other.
Jared Freid
Right.
Jack Maloney
And like, there are many ways, I think what becomes challenging about trans. The trans experience is like, when I was overweight, I. I could decide what I wanted to do about my body. And then that decision and the autonomy I had there changed my outcomes. And that's not me saying everyone should lose weight today, but I just felt like, oh, because of. I know. I know. The environment of gay men and of gay dating. I was like, I feel like maybe if I lose some weight, maybe I'll have better chances. Turns out I did. I had to make peace with the fact that that was a truth, because I think I also had to realize I was just as beautiful when I was heavier as I am now. I'm no different now, internally and even, honestly, externally, even with less weight. And I had to get to a point for myself where I could say, you are so beautiful and you deserve love in the mirror. When I was at my heaviest and felt physically the ugliest I ever was. But then I had to realize, if I keep saying that to myself and about myself, I will never exude the energy of somebody who is attractive.
Jared Freid
Well, but also. But also, this is the thing you can't really get ahead of. Like, you can tell yourself how to feel and try and work on that, but then your friends say one thing that doesn't fit in line.
Jack Maloney
Yeah.
Jared Freid
With the way you would wish them to act.
Jack Maloney
Yes. And on that note, I want to really shout out too, that my journey and the things I just talked about are much simpler, I feel, than the trans female experience. There's so many more barriers. Let's even talk about the fact that she's, like, for context, I've not medically transitioned. Okay. Well, there's a million reasons why that might be. It's expensive, it's inaccessible. We don't know where she lives. Is. Is it even legal anymore? I mean, we're in a time in our country where that's becoming a problem too.
Jared Freid
You know, beyond that, she just wants someone to go, you're into men and you want to be thought of. Like, to simplify, like, well, thought of in the context of dating.
Jack Maloney
Yes.
Jared Freid
Like, you want to be thought of. You want to be in the conversation with your friends. And right now, this is a show that your friends aren't thinking of you as an option for someone who might want to Date you. And then they're assuming for them and now you're seeing it. That's the problem is I'm getting an honest answer from my friends. And before I was getting a maybe not as honest answer. And I think to say to your friends, hey, I told you I wanted to maybe date this guy. I think this is like an argument with the friends. The guy is like kind of separate. Like, I think to my friends, I would be like, hey, when I brought. If I wanted to have this, I was.
Cozy Caravan Sponsor Voice
These were.
Jared Freid
And I would have to decide, are these close friends of mine?
Jack Maloney
Well, here's the thing too. It's like, really what I'm hearing through this as well is like, your friends see you as a woman until it becomes about sex and dating.
Jared Freid
Right.
Jack Maloney
We're talking about straight men specifically. Have you ever been on a date with a trans girl? I have ever, like masculine on a nap or anything like that. I don't feel like that you would have known about. Okay, yeah, I didn't.
Jared Freid
You know, I have seen trans women on the apps and have not matched or if I had, I actually unmatched. Because it wasn't for me.
Jack Maloney
Huh.
Jared Freid
And.
Jack Maloney
And what wasn't for you? I'm just kind of curious.
Jared Freid
I just. You know, what wasn't for me?
Sponsor/Ad Voice
It just, I guess it was.
Jared Freid
It was far outside of what I've known or understood. And I think that, you know, what the unknown is fear.
Jack Maloney
Yeah.
Jared Freid
And what were you afraid of? Does it feel. Probably the, the. The. Probably a million different things. You know, there's. There's outside judgment that I'm not, you know, you're not proud to say that, but that's probably a good. It's also like to hear. It's also like what I. What I've known. You know, we stick to what we have known and what we've been brought up with.
Jack Maloney
Right.
Jared Freid
I'm a straight guy. Does that change my. Like, am I looking to have the conversation with myself that would be included?
Jack Maloney
Yeah.
Jared Freid
At 40 years, like, this is all things that, like, you know, it's like you can't really control that like that.
Jack Maloney
It's so interesting that you say that though, because that's. I think what I was sort of. That's one of the main things that comes up in my. My brain is, do straight men feel like if they date a trans girl, that their identity is somehow not threatened, but in flux or in a. In a way that makes them uncomfortable?
Jared Freid
If you want to think about the plight of a straight man, which no
Jack Maloney
one's really the plight of a straight man. I, I, I, I'm deeply interested. Tell me about it.
Jared Freid
I like, I talk a lot about like a finger in the butt during a blowjob that I'm like, that is pretty amazing. It's like putting bacon on a cheeseburger. Okay. And when I talk about that, I, and I think it's, it's funny, but it's also like it, it's pretty unbelievable. I'm okay with that. I've, I've jokingly referred to myself as the Rosa Parks of straight male ass play. I'm okay with my sexuality enough to have that out and make those jokes. But there's someone out there who's like, finger in the butt during a blowjob. No fucking way. They don't know how to deal with it. In the way I kind of stammered on about dating a trans woman, I would think that they have a similar thing. The problem as a straight man, and this isn't, this is just society. I'm not going to fix this. A woman coming out and saying, well, he likes, you know, if I said if I went to a bar and I was in an argument with my girl, my ex girlfriend, I said, well, she likes like if. And she walks in the bar. We're at a bar, my ex walks in, she screams out, he likes a finger in the butt during a blowjob. Everyone's like, whoa, whoa. There's like a, there's a reaction, there's a, what's his deal? Is he off? Is he different? What's going on? If the reverse happened, If I walked into a bar and my ex girlfriend was there and I was like, she likes a finger in the butt. When I go down on her, everyone's like, all the men there are going, oh, that's pretty hot. I think straight men are not allowed to have a wide spectrum when it comes to their sexuality.
Jack Maloney
Now that's something that's, that's also okay. Now that's something to explore.
Jared Freid
Well, this is, this is my point with, yeah, the butts, right?
Jack Maloney
Yeah, yeah.
Jared Freid
I am judged on a dip. Oh, so he loves that. That's what the response would be. No, I did it once and I liked it.
Jack Maloney
And I liked it.
Jared Freid
Right. That's how it all. If I told a girl, like, so
Jack Maloney
you're saying that you feel like that judgment comes from women?
Jared Freid
Oh, yeah, of course.
Jack Maloney
Interesting.
Jared Freid
Of course it comes from everyone, but especially women, you know, Like, I, so I think like, again, to go back to, to the, the email of the trans Woman. Like, there's a lot of stuff to cut through.
Jack Maloney
There's a lot.
Jared Freid
And I don't.
Jack Maloney
You could talk about it for an hour or two.
Jared Freid
This podcast for a day has always been about, like, telling the weather and to bring an umbrella. So, like, I think to her, if I was like, you know, we start with my friends and like, hey, I'm a little annoyed at you guys that I was, like, ignored, and I felt like I was, like a crazy person for being like, I want to date that guy, give him the opportunity, and I'm not gonna make him evil if he's like, that's not for me. You know, that's okay to say.
Jack Maloney
That's not for me. She even said that she's like, I'm. I understand that. I'm not expecting everyone to be attracted to me.
Bilt Sponsor Voice
Right?
Jared Freid
And I think she has to deal with the. Amongst the many plights she has to deal with, like, I'm not. I'm not envious of that. She also has to deal with the men she wants to date having to deal with whatever they're dealing with. Right. Socks.
Jack Maloney
So I think in everything you're saying, I. I hear a few things. One, the patriarchy is doing us all dirty because we can't.
Jared Freid
We all. It's doing.
Jack Maloney
It's all dirty because you've. Your sexuality as a straight man even feels like it has these boundaries because of expectations, the plight of a straight man.
Jared Freid
Right? And because of the embarrassment, of course, you know, put into 100.
Jack Maloney
And then you have trans girls who just want to be seen as women, right? But also, you know, want to be seen as everything they are and just want to be considered, right? Just want to be visible, seen, validated by their friends, by. By men, right? And so I would say I challenge you and all straight men out there, right, To. If you know that your anxiety, your fear of maybe endeavoring a trans woman comes from society, then maybe push past.
Jared Freid
Like.
Jack Maloney
Like, challenge yourself to push past it.
Jared Freid
It's funny.
Jack Maloney
If you could be open to it.
Sponsor/Ad Voice
Well, it's funny.
Jared Freid
It's like, listen, that would be a nice thing. Yeah, but, like, we're even seeing in this email, even their closest friends are the ones in the way of that. Do you know what I mean? Like, who do we start with? Who do we start with? The random guy who's listening to this.
Jack Maloney
Like, to me.
Jared Freid
Do you start with me? Who's like, I don't know. That would be like, again, that's something I'm not, like, like, proud to say out Loud that I'm not the most open and ready for that type of guy.
Jack Maloney
You know what?
Jared Freid
I don't even know if proud is even the word. But, like, I'm like, I hear the friends. I go, well, the friends aren't even allowing for that to happen.
Jack Maloney
But you know what, Jared? I actually do think it can start with you also you or yes, you or any man who's willing to push past that societal anxiety. Because we have the Internet, we have phones, we can talk about our stories and share our stories. And I know my trans best girlfriend is always showing me a lot of videos about trans girls online. Being like, dating is so hard. Dating is that. And she, she's like, there's no good examples of actual successful relationships. If you become that or someone else like you. Like you becomes that, you start to break that barrier.
Jared Freid
Jim Norton, that someone we gotta have on this show. Jim Norton, famous comedian, been. He was on O A back in the day. Jim Norton. His wife is trans, I think. So we gotta have him on the podcast. I mean, we've been actually, we had him scheduled and we were trying to make it happen. That'd be cool. But. Jack Maloney, thank you so much for.
Jack Maloney
Thank you, Jared.
Jared Freid
Always a pleasure. Everyone go follow at the Jack Maloney We Are the U podcast. It's every Wednesday and Friday.
Sponsor/Ad Voice
It's a Friday feels.
Jared Freid
So we will see you next week. Boom.
Sponsor/Ad Voice
Thanks again to Sonic for sponsoring this episode. Remember, if it's not showing up hot, not giving you what you want, and costing way too much, you're allowed to walk away. And when you're ready, Sonic's new All American Smashers are here for you. Hot off the grill, they're premium hand smashed with Angus beef, made to order and loaded with classic ingredients like lettuce, tomato and melty American cheese. All at a price that actually makes sense. Break up with your burger and try the Sonic six dollar All American Smasher meal instead.
Episode: Should You Break Up Over Bad Kissing?
Date: February 27, 2026
Hosts: Jared Freid (comedian) & Jack Maloney (guest host)
Main Theme: Navigating modern dating dilemmas—primarily, whether “bad kissing” is a valid reason to end a promising dating situation. Also, broader issues around intimacy, vulnerability, perception in relationships, and advice for underrepresented daters.
In this engaging, candid episode of the “U Up?” podcast, with Jack Maloney stepping in during Jordana Abraham’s maternity leave, Jared and Jack explore a listener’s question: Should bad kissing be a dealbreaker after a string of otherwise promising dates? The duo offers humorous anecdotes, emotional insights, and direct feedback, also branching into deeper questions around attraction, intimacy, queer dating experiences, and inclusion. They tackle three main listener situations: “bad kisser—ick or picky?”, the social fallout of breakups, and dating as a trans woman.
[02:05–04:53]
[05:49–19:02]
Notable advice:
[21:32–27:03]
A listener broke up with her BF shortly after he lost his job; he’s now spreading that she “only wanted him for his money.”
[27:56–42:35]
A 24-year-old trans woman shares her pain: friends affirm her identity with pronouns/names, but never consider her “a real option” for straight male friends. She worries about being invisible or written off before being given a chance.
For full stories, relatable laughs, and more advice, follow the U Up? podcast on Instagram @u.up.podcast or subscribe for bonus content.