Judgement Call
Judgement Call
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Oct. 22, 2026

MARRIED TO AN INMATE: LOVE OR RED FLAG? A JUDGE DECIDES

MARRIED TO AN INMATE: LOVE OR RED FLAG? A JUDGE DECIDES
Judgement Call
MARRIED TO AN INMATE: LOVE OR RED FLAG? A JUDGE DECIDES

Why do some couples make you question everything you thought you knew about relationships? đź‘€ Judge Lynn Toler and Dr. Ish Major get into the dating debates that have everyone talking, from major age gaps and partners behind bars to sugar daddy secrets and money changing the meaning of romance. They also tackle a parent's worst nightmare: what do you do when your 20-year-old starts dating someone who's 44? It's a conversation about trust, attraction, power, and the choices people make for ...

Why do some couples make you question everything you thought you knew about relationships? đź‘€

Judge Lynn Toler and Dr. Ish Major get into the dating debates that have everyone talking, from major age gaps and partners behind bars to sugar daddy secrets and money changing the meaning of romance. They also tackle a parent's worst nightmare: what do you do when your 20-year-old starts dating someone who's 44?

It's a conversation about trust, attraction, power, and the choices people make for love, money, and everything in between.

Tune in to Judgment Call, then subscribe, leave a review, and share your verdict. Would you support these relationships or have some serious questions?

00:00 - Why “Odd” Couples Fascinate Us

02:22 - Marrying Someone Serving Decades

10:02 - Age Gaps And The Baby Clock

14:45 - The Sugar Baby Secret Marriage Fight

25:02 - Fantasy Selling And Transactional Dating

34:32 - Parents Confront The 44-Year-Old Boyfriend

44:22 - Fair Exchange, Clear Rules, Closing

Why “Odd” Couples Fascinate Us

SPEAKER_05

She's seen it all from the bench. He's helped couples through it all. Now they're making the call on the internet's biggest relationship debates. Real relationships, real reactions, real talk. This is Judgment Call.

SPEAKER_07

Have you ever seen a couple in a restaurant, walking down the street, somewhere out and about, and they just don't seem like they fit. Like they just don't look quite right together. Remember, we were in that restaurant that time, and we saw they were so co cozy and lovely. She had to be 21. He had to be 70. And it was just, and we were looking, and you looked and I looked and we looked at each other. And what is that? I mean, I mean, I don't know the know that I don't know their circumstance. I don't know their situation, but what happens when you have gaps like that?

SPEAKER_09

Yeah, you know, it's one of the things I missed the most about living in New York because we would see the fricks and the fracks together all the time, and we just didn't make sense of it. So it's it's a big phenomenon when we talk about relationship dynamics, and it's just it's our moments of humanity. Most of us wake up and we don't feel all the way complete or all the way there. So we're subconsciously looking for that other person. We literally call them our other half, our better half to help complete us. Let's say I'm a person who doesn't say no well. Well, I want somebody who can tell people no immediately because now when we're together, I can let that that's your job, right? You it's time to say no, you're on, do your thing. And now we can feel more complete together. So that's a very interesting thing. And it comes in the package it comes in, whether it's an age gap, a wealth gap, an attractiveness gap, as long as you've got the intangibles that suit me and help me feel more complete, then I can rock with you.

SPEAKER_07

Yeah, yeah, and and they have their relationship has no obligation to look right to me. I'm just being nosy and busybody matters, but I think it's fascinating. So we have a few of these here today to talk about. Madison, could you give us our first uh Mitch Matt? Mitch. Could you give us our first Mitch Matt, our first couple?

Marrying Someone Serving Decades

SPEAKER_01

Judgment call.

SPEAKER_00

My husband is serving 23 and a half years in prison, and I met him 10 years into his sentence. These are some of the smaller things that come with being in a marriage like ours that I don't think most people think about. I got my iPad and I've got notes. So I'm being serious about this one. Number one, we are not celebrated. If it was not for me coming on TikTok in 2020 and sharing my journey with my husband and having all of you amazing, supportive girly pops, I really do think that my marriage would just be completely in the shadows. For example, any milestones, I still aren't recognised. So we just celebrated our five-year wedding anniversary this year. Personally, I mean not everyone's the same, but personally, if I had a friend who celebrated a five-year wedding anniversary, I think that's quite a big milestone with like anniversaries, I would send them a card. Or if they were in a situation where their husband was not physically with them, like mine isn't, I would take them out for dinner or I'd take them out for drinks. I just want to do something with them to know that like their marriage is celebrated. But yeah, we don't get none of that. Number two, we aren't taken seriously even when good things happen. So we might be celebrating something, a big achievement, or it might just be something small that I want to gutch about. And I can just tell people aren't fully excited about it because I can tell in their head they're thinking, yeah, but he's also in prison. They also like to throw in a comment or two when you're busy gushing or excited and happy about something like that's nice, but wouldn't you rather be with someone that's like not in prison? That's not what I was talking about, but thank you. Thank you for that. Leading nicely into number three. If I vent about anything, anything, it could be that me and my husband disagreed on how long you should cook pasta. Their go-to response is leave him. Girl, leave him. That is not worth it. You're already going through enough. Wouldn't you rather be with another man out here? I don't know how you do it. I don't know how you do it. I think you should leave him. This isn't worth it. You're so young. You're so young, you've got so much luck, you're so beautiful. What are you doing? Just leave, just leave.

SPEAKER_07

I gotta say this right off top. There are a lot of issues, problems, and complications that I might imagine uh would be involved in a marriage with someone who is incarcerated. She didn't talk about any of them. All she did was talk about how the relationship looks to other people and how other people are responding to the relationship. It was more important that it was the problem, was the world wasn't celebrating her relationship, and the world wasn't, you know, giving them accolades and sharing them on, as opposed to what are the real issues involved in loving someone who is incarcerated. That's just me, though.

SPEAKER_09

Well, listen, uh, at that point, that's where my ears perked up, too, because what she's talking about is all the secondary gain she's getting from being with the person who's incarcerated, as opposed to the primary gain of how it helps me feel.

SPEAKER_07

Right. Right? Right. Yeah. And then no talk about love, no talk about you know how often they got to see each other or the difficulties with that or the complications with that. It was just that the world doesn't see us as a couple, and that distresses me. I there's a lot more important stuff going on.

SPEAKER_09

Yeah, you know why the world doesn't see you as a couple? Because you're not, because he's in jail where he's gonna be for the next 25 years, okay? So uh let's just be honest, right? Being a being in a relationship, and my God, I I we I do a whole show with folks who were incarcerated and now they're out. And how do we marry these two worlds and move together as one? But she looks super young. 25 years is a very long time to commit to being alone, a very long time, right? And so when you that you're not obligated to commit to 25 years of loneliness because he committed a mistake, right? Right? You're obligated to do that, and when you're and when you're in that dynamic, my question to her is who are you being loyal to?

SPEAKER_07

Right, right. And why I always ask myself in these situations, what would I do? You know what I mean? I wouldn't marry somebody already incarcerated, but I always wonder if something my husband did something incarcerated, what would I do? I think if I think I think if he was not guilty and incarcerated, or he did it for a good reason, I'd I'd stick with him. But if it was something I told him not to do, I'd be mad.

SPEAKER_09

And then it was and if you were and if you were 22 and he got 25 years, would you still make the same decision? I don't think my parents would let me. Right. That's a long time. So I yeah, I hear a lot of um, I think when we talk about the psychology behind it, we all show up in the world and we make the decisions based on those six human needs that we all have, right? Some of it's and and how we prioritize it. I am an OCD to the core human being. I have a primary need for certainty. I want to know what comes next, and then what happens after that, and then the next thing is so certainty is a need, uncertainty is a need. One of the big human needs these days is for insignificance. We all want to be important. Attention, right? We want attention, and she's found the thing that helps her get attention and makes her feel significant and seen, which is I am young and beautiful, and I'm dating the guy who's gonna be in jail for the next 25 years.

SPEAKER_07

What's he got for me? What she got for me? That's that this is me. So who's the judgment call for? Well, let me think about that. I wish her well. Um, but that 25 years is gonna get along. I guess he's got 15 left. Was he already in for 10?

SPEAKER_09

Yeah, I think he's already a bit in for 10. He's got a few a few left. And the big question is, like you said, were we together before he went in? Was this did this kind of happen afterwards? That's gonna be a big thing. Here's my judgment call. My judgment call is for father time, because that man ain't never late.

SPEAKER_07

Yeah, that's true. That's true, right?

SPEAKER_09

And the day wins out, right? At the end of the day, Father Time wins out. Uh, and the thing we do today, you are you are young lady, you are under no obligation to be the same woman five minutes from now who you were five minutes ago. No, right? Uh, and I I hear you you said it one night on boot camp, and you were like, listen, when you see me walk across this floor tonight, you should take a picture because the woman you're gonna see next week, different woman.

SPEAKER_07

Because I got to level up every day, I got to do something different, something better, something, something that's that's more, but I'm never it's I'm gonna be somebody different, right?

SPEAKER_09

Right. And what she's got to realize is when he went in the the day he went in, there's this thing called arrested development, right? Emotionally, he doesn't progress in prison. He's gonna come out the same as when he went in. You, young lady, are gonna be a very, very different person. Right, and so now that dynamic may not work, and that's gonna be a hard realization when you come face to face with that reality. So judgment call for judgment call for fall the time. She'll he'll help her figure it out. He's gonna help her figure it out, as my mom would say, by and by judgment call.

Age Gaps And The Baby Clock

SPEAKER_06

For all the people that have problems with age gap relationships, uh, try being a 33-year-old man with no children, a good career, and just wanting to start a family. And try to find someone your own age to start a family with. It's impossible. 33-year-old woman. So let's say I find a 33-year-old woman, I marry her today, and we have kids tomorrow. Her first child, well, her first child with me is going to be at 33 years old. That's like not dangerous yet, but you're starting to get there. Now let's work our way like seven years down the road and say we want to have a second or third child. Well, now she's like 40. That's unsafe.

SPEAKER_07

People out there making too many rules for themselves. Do you understand? You you you know what I'm saying? He's 33 years old. My age is anywhere from 26 or 25 to 30, to 34 or 35. I mean, it doesn't have to be exactly 33. And, you know, I had my first baby at 32 and my second one at 35, and then, you know, women are having babies later. I don't know. He just thinks like he's looking for an excuse not to, you know, I don't know what he was doing. I don't know what point he was trying to make.

SPEAKER_09

Well, you listen, as you said it was you said it the best, the more rules you have about your love life, the more you set yourself up for different ways to get disappointed. Because I don't know if you know, I don't know if he's ever dated a human, but they are highly unpredictable. Highly unpredictable, highly unpredictable. And so, like you said, okay, no, so now let me let me put on my doctor hat. Listen, uh, you can have, and for all my OB uh colleagues out there who tell me, listen, you can we we do not mind a woman coming in up until the age of 40 to safely help her manage that pregnancy. We don't like it over 40, but it's still not entirely unsafe. We can help you get through that as well, right? As they say, we have the technology, so he's he's making up a set of rules that's not based in actual reality, also, because you know, there's there's not as much runway as women would like, but there's more runway than we traditionally think when it comes to those child-bearing safe ages.

SPEAKER_07

Right, right. And and he's just putting limits on himself, and it doesn't seem reasonable, rational, or or something he needs to do.

unknown

Right.

SPEAKER_09

Well, Josh, have you ever noticed how when people come with come to you with their love story, whether it's uh you know, all men cheat, uh dating is a game, dating is a jungle, your mind has this subconscious way of making it come true.

SPEAKER_07

Oh, absolutely, absolutely. If you keep worrying and and and feeling that way about something, you you you you ultimately drive yourself in that direction, and that's where you end up. So, you know, if you put the scenario in your head, well, then seven years later we were gonna have a kid, most people don't wait seven years from one kid to another. He's putting in a whole lot of boundaries and barriers that aren't really there, like I have this problem. No, you don't. You're 33 years old, don't have any kids. You've got options, options and options.

SPEAKER_09

Right. It's just as easy to rehearse happiness as it is easy to rehearse chaos and disappointment. That's so true. Right? I you can it takes the same amount of mental effort and mental energy, right? It's the same amount of emotional labor. So, what would happen if you rehearsed a different story? If you told yourself a different narrative, you know what? I'm 33 and I'm young and I'm vibrant and I'm good looking and I got some stuff going on, and I can't wait to wake up this morning. Right, and see what the universe sends me.

SPEAKER_07

You know what I mean? Right. Absolutely. So judgment call, not but it not for him, but I judgment call. I don't I don't know who whoever misses him.

SPEAKER_09

I yeah, just listen, judgment call for um judgment call for being able to buy a buy a buy a pen and rewrite your love story. Right.

SPEAKER_07

Yeah.

SPEAKER_09

In a way that's gonna come out the way you want, you know?

SPEAKER_07

Yeah, things that I don't know these days, people seem to things happen to them as opposed to they are the author of their own story. You know, I'm in this position, I'm in one of these groups, and in this group, I'm not seen, or I'm not validated, or I'm not as opposed to, well, here's today. What am I gonna do with it?

SPEAKER_09

Right, that's right, that's right. You're right, you're you're a co-creator of your life. Right, you have some say the life is not happening to you, it's happening for you if you can relax and let it judgment call.

The Sugar Baby Secret Marriage Fight

SPEAKER_02

Am I the asshole for telling my wife that I never asked her out if I knew she was a sugar baby? I've been with my wife for five years, married for a little over one year. I was doing some cleaning and I came across something I'd never seen before. It was my wife's old jewelry. I knew she had it, but I just never noticed how expensive looking it was. I asked my wife out of curiosity, where did you get this and how much are they? She told me they were from an ex and they cost an ass load.

SPEAKER_09

I'm sorry, Madison. Uh, do we have a definition for the numerical figure for ass load?

SPEAKER_02

She told me before that she only had one ex back in high school and they dated for a little bit in college. I asked her, how the hell did a high school kid afford these? She looked confused, and I reminded her that she only told me about the one ex. There was an awkward silence, and I told her that it was up to her, did she have another ex? And if so, why did she tell me she only had one? She tried to play it off, but I pressed her. She confessed she had several sugar daddies for about three years. I was mad but kept calm. I asked her why she never told me that she was a prostitute.

SPEAKER_09

She tried to give me the spiel about he said that to her out loud, or is that what he thought?

SPEAKER_02

Uh I asked her why she never told me she was a prostitute.

SPEAKER_07

She said it was not out loud. He said he said it.

SPEAKER_02

She tried to give the me the spiel about how it was more a relationship but with gifts. And I told her to cut the crap. She told me I was afraid. She told me she was afraid I was gonna judge her. I told her I was seriously mad and she shouldn't have kept this from me. She says, Does it matter? And I told her it matters. She asked why, and I told her I would have never asked her out in the first place if I knew. And she straight up lied to me when she told me she only had one ex. She told me she did only have one ex, and that just pissed me off more. I quoted her saying, Didn't you just say the sugar crap was more like a relationship? She did cry and say sorry, and she'd do anything to make it up for me. She did cry and said she was sorry, and that she'd do anything to make it up to me. I told her I need some space. I don't know. I'm pissed. I do love my wife, but I feel robbed of my decision. I do mean what I said. I would have never asked her out if I knew back then.

SPEAKER_07

That's a lot of information to keep from somebody. It really, really is. But my question That may be the most politically correct thing I've ever heard you say. I think there's a difference between prostitution and being a sugar baby. I mean, there there's the qualitative differences. I'm working hard here, Ish. Help me out. Don't just laugh at me.

SPEAKER_09

Listen, I think I think you're 1000% correct. Listen, if can if can we be honest about it? As long as there has been dating and as long as we have been coupling up and uncoupling, there's never not been a wealth for beauty exchange. There's never not been a wealth for age or youth exchange. There's never not been a wealth for status. There's always, I'm always getting something, you're always getting something. I'm always giving something, and you're always giving something. There's always exchange, you just gotta be okay with it.

SPEAKER_07

Right, exactly. And and then the sugar baby thing is just more of a of an accurate light on the exchange. We're not we're gonna call it what it is. Right. We're just being very pragmatic. Yeah, very pragmatic. I guess my second question to him would be are you happy now? In other words, you've been five together for five years and you've been married for one. Absent this news, were you happy? Because if you were happy, you gotta ask yourself, what does this news change? Sure, she loses some points in the in the trust department, but if you're happy and you're getting along, being denied that decision whether to ask her out at first or not seems to me to be a moot point.

SPEAKER_09

100%. Um Yeah. What is what does that change for you, right? What is this what is this information change for for you other than the lens through which you view her? Right. Right? Um, you know, and I hate the fact that you know the default setting when men get angry, when men get hurt, when men get insecure with the woman in their life, the default insult is to insult her virtuosity.

SPEAKER_07

Yeah. Body count's a big thing with guys, yes?

SPEAKER_09

Body count's a big thing with guys, uh, but when the situation's reverse, body calcity is it's a great thing with guys. So I don't like that he went there. She's got a right to have had a life before you, she's got a right to have dated guys who she deemed worthy uh before you, and she's got a right to keep some of that secret. Like you said, there's a lot that he should have known for sure, but what does it change other than the lens? Right. You know what I mean? Other than the lens, what does it change about the woman you now know and who you've been happy with, I'm assuming happy with for the last five years. You know what I mean? Yeah, yeah.

SPEAKER_07

I you know, now she should have told. I mean, it would it was a whole lot of information to keep from somebody, and I can't imagine anybody not having a whole set of funky feelings behind that. Um it's not something fun to learn about somebody, but I just want to know, are you happy now? And is the change in that lens worth losing that happiness?

SPEAKER_09

Right. Um, and when we're trying to get to the truth of things with the person with the person we love, you've got to remember the rule, right? You always in a relationship, you're always trying not to hurt anybody you love. And you're getting information from this woman who you love.

SPEAKER_08

Right.

SPEAKER_09

What you can what you can't do is call her a hoe and then expect things to go back tomorrow, like it was because when you call her a prostitute, that's all she's gonna hear, and she's never gonna unhear that. That's just an ugly thing to go.

SPEAKER_07

Yeah, she should she could have done herself a favor after dating for a while. She should have been a little more clear about what she was doing. Give that man, because he does have the right to know all the information about somebody before he gets involved with her. I just don't want that information to to be so overwhelming that it hides. A true happiness that happened to be there just because he didn't know.

SPEAKER_09

Right, right. She's allowed to discover different parts of herself just like he has. You know what I mean? And so it speaks to a larger point where, especially as we as we talk about what are we bringing to the table these days, and women with their 666 rule, he's got to be six feet tall and make six fingers, six figures, and have a penis over six inches long, which puts you in the top one percent of men in the country. So there's never and and he should pay for everything. So, okay, so if I show up and we go on dates and I pay for all the Ubers and I pay for all the dinners, and if we do weekends away, and I pay for all the weekends, is that prostitution? Because we're we're exchanging time for value, the money's coming out of my pocket, and what I'm getting for you is something in return. So what do we call that? Right? There has never not been an exchange system when it comes to dating. You just gotta explicitly state the rules and make sure that you are both okay.

SPEAKER_07

Yeah, everybody's consented it's consented to the rules as stated. Right, right. So who's the judgment call for?

SPEAKER_09

Uh, the judgment call is for that ass load of expensive jewelry. I want to see what that looks like. Wait, and why is she still keeping it? Where, first of all, why is she keeping it? Where is she hiding it? What I have so many more questions.

SPEAKER_07

Yeah, yeah. I think I've I'm gonna give it to him just because he has had a gut punch and he's got a lot of things to think about, and I just don't want him to make the wrong decision. And I don't know what the right decision is. I'm not saying stay, I'm just saying consider how happy you are if you are really happy.

SPEAKER_09

I wonder if there's anything about the current way their relationship is set up that makes him concerned that he may also be in part or in whole a sugar daddy now. You know what I mean? Yeah. Uh in terms of, oh my goodness, well, does that mean that when I did this, was that's more of a sugar baby, sugar daddy situation? Or am I really your guy? Right. The question I hear him asking underneath is are you in this thing with me for real or not?

SPEAKER_07

Which is a very good point. And that might very well factor into his decision as to whether or not this information is gonna alter what he does. And that's more important than not knowing in the beginning. It's how does that frame her for you now?

SPEAKER_09

That's right. That's right. I would hate, I would hate for him. Yes, it's a lot to absorb, but I would hate for him to miss out on what could be one of the coolest things of his life because of the lens he's viewing her past behavior that she engaged in before she met you.

SPEAKER_07

Yeah, but she didn't have told him. She shouldn't have told him. I'm judgment call for him. Or sell the jewelry for God's sakes. Yeah, give him, yeah, right. Help with the bills a little bit. Right, right.

SPEAKER_01

Judgment call.

Fantasy Selling And Transactional Dating

SPEAKER_04

How many sugar daddies do you currently have?

SPEAKER_03

In a good year, I like to have around like 10, and then they all give me like $10,000 a month.

SPEAKER_04

They all give you $10,000 a month.

SPEAKER_03

Yeah, yeah.

SPEAKER_04

So you make $100,000 a month?

SPEAKER_03

When I have $10, yeah.

SPEAKER_04

So do you meet up with these guys?

SPEAKER_03

Sometimes. Like a lot of them live in New York or San Francisco. They fly out. They do, but I never really meet them. Like, I don't know, I just make up an excuse that I can't see them or something. Like, I just finesse. I literally just finesse.

SPEAKER_04

So fraud. Okay.

SPEAKER_03

But I've gone on trips with some guys before too, but they just want me to be around them. Like they just want to be seen with me. It's a win-win for everyone.

SPEAKER_04

So when you say finesse, what do you mean?

SPEAKER_03

I am basically selling them a fantasy. And that's all it is.

SPEAKER_04

What's the fantasy?

SPEAKER_03

That I'm interested in them.

SPEAKER_04

But you're not.

SPEAKER_03

No.

SPEAKER_04

Okay. And so you would say, hey baby, can you pay for my rent? Yeah. Can you buy for my app?

SPEAKER_03

Oh my gosh, this dress would look so good on me. Like, let's let's go shopping for dinner. I want to go on a date with you. I need an outfit for the date. Bam, outfit. Oh, I I need to, you know, drive up to see my family. I need a new car. Bam, new car.

SPEAKER_07

If you would, please, Josh, please. I find it distressing that this has become such a I don't know. I mean, I understand what you were saying about there's always been an exchange of money for beauty and you know, get married and good-looking women get these rich guys, and rich guys go after good-looking women. But the way she put it, like I finesse them. This is not an exchange. This is this is fraud. As the man said, she, you know, I'm defrauding guys, I'm playing with them. I'm not giving them the proper exchange that I asked for. And the proper exchange that you asked for might be really legally prostitution. So I just I don't know. I as a matter of law.

SPEAKER_09

Yeah.

SPEAKER_07

I struggle with the concept greatly, even though I don't condemn the people that do it.

SPEAKER_09

Right, right, yeah, yeah. So, you know, listen, I live in Miami, uh, and I'm not sure if you're aware, but this is the number one uh city for content creators in the country. Uh, YouTubers, our TikTokers, and this is the number one city for OnlyFans models, right? I did not know that. In the country. So I'll tell you a little story, Jabs. I'll tell you a little personal story. A little personal story. This is gonna be good at the risk of not oversharing. The number she shared, the $10,000 number, that is that is an accurate number. Met this young lady a couple months ago. Lovely, beautiful, you stunningly gorgeous. Oh my god, I couldn't believe my luck. And in a town like Miami, we met. She's from the same small place that I grew up. Are you kidding me? Where were you when I was there? Do you know that? Yeah, I know that place. What about had some common background, had some common history, were into some of the same same things, had an amazing first. I mean, a fantastic, couldn't stop just loving the conversation. It was like all into it. She's like, you know what? This is cool. We had a really cool first date. Uh, not sure if you realize or recognize who I am, but I am, in fact, an OnlyFans model. I was like, Oh no, I I didn't recognize. She was like, Well, let well let me show you. Here it is. Sure enough, that's what she does. And then right after that, she's like, and having that said, just so you know, um, I would love to go out with you again. I mean, I think you're wonderful. I'm very attracted to you as well, just as much as you're attracted to me. But there might be the small matter of a fiduciary responsibility we need to discuss before we go to that second date. And if you wouldn't mind helping me out with a small nominal fee of ten thousand dollars for date number two, and moving forward, I don't think that's an unreasonable ask given who I am and given that my last boyfriend did the same thing. How fast did you run? I'm still running, I'm still running. Um my legs are tired. I got my can you and listen, no judgment. I'm not here to judge you if that's if that's where you are. I respect the fact that you had the guts to ask for it. I do. Yeah, she said it outright. She said it outright. So I respect that. Now you should respect the fact that, and I'll tell you what I told her. I was like, listen, I I get it. You know what I mean? I mean, there's you're young and you're beautiful, and there are a ton of guys out there who would gladly fork over that 10K just to spend some time with you, but I'm not one of them because what I'm looking for is something a little more real. You know what I mean?

SPEAKER_07

That's why I feel so sorry for for love and and and and romance and marriage in this age, is uh everything is so transactional, nothing is just like, hey, I like you, you like me. We cangether, build something together, or not even build anything together. We just gonna be together because we like each other, you know. Everything doesn't have to be a you know, a Jay-Z Beyoncé super couple, you know. I'm an entrepreneur, I want you to be an entrepreneur. You can't just love somebody and just sit home and be in love.

SPEAKER_09

There's this sentiment in the dating scene now that says people are looking for partners, people are just looking for help. Because everybody's struggling.

SPEAKER_07

Yeah, we're really disconnected these days. It's a frightening thing.

SPEAKER_09

We are, we are now. This young lady here is gonna get herself in the trouble because, in the spirit of any fiduciary responsible agreement, there's a fair exchange of goods. Exactly. Exactly this is not a fair exchange when he's sending you money and then you are uh pulling the oakie doke and dipping out. That's gonna catch up to her sooner or later. Uh, there are two things that have that are undefeated on this planet father time and mother karma. And that karma's gonna catch up eventually.

SPEAKER_07

Yeah, I just the the whole idea of it being so transactional and you know, I mean, just it I oof well it spoils it, and the word I used for her, I was like, I was like, honey, I gotta tell you that feels a little icky to me.

SPEAKER_09

You know what I mean? Um, that's fine for you, but I don't think the way I the lens I view myself through says that I'm not the guy who has to show up and pay a fee for somebody to spend time with them. Yeah, right, right, right. Uh and on the other side of that, what is that? What is that? What's the other message it says? The the other message it sends says, you know what, dude? The idea of me spending a moment with you is so detestable to me that I'm gonna require a financial deposit in order for me to wrap my head around.

SPEAKER_07

Enumeration, yeah, yeah. That's it's uh it makes me sad. It really makes me sad.

SPEAKER_09

Well, it I'm still sad about it because I adored this person, and as you guys say in the legal world, if but for that, you're right, right, right. Then I was like, oh my god, this is I just met my person. Holy cow, she is absolutely fantastically wonderful. The fact that she asks for money doesn't change the fact, but it just means that she may not be my person. That's the space where she is in right now.

SPEAKER_07

Yeah, I I hear what you're saying, and I'm trying to be more equanymical, uh, more I don't know. It's got me so confused, I can't speak.

SPEAKER_09

Uh well, it's uh it talks about it speaks to the point, the larger point of why 50, almost 60 percent now of our guys under the age of 30 are happily single and not looking for anybody because there's something has soured the waters, you know. Yeah, and I'm not sure anybody's really quite figured out what it is. It is no one thing, as we say in medicine, it's multifactorial, but a lot of people, men, women, and everybody in between are really just soured on the idea of finding some true love, you know? Yeah, it's unfortunate. It is, and you know, my folks were married for 56 years, right? That's then that's them right back there. So I believe in the true thing, I believe in the real thing, you know. I one of the one of the things I love about our friendship are the stories you tell me about you and Big E, right? Because it helps me understand that it's possible.

SPEAKER_07

Yeah, right. We can we can possibly but but you gotta let the transactional part go. You gotta let the the the the you know the that that that sense of I gotta give you this for that, you gotta let that go. I don't know. I just I'm sad for us in that respect. Yeah, yeah.

SPEAKER_09

Well, you know what? That young lady taught me something because I I thought there were only five love languages, love languages. She taught me that there was a six. Because when I asked her, I was like, well, help me understand, help me understand the dollar figure, help me understand the 10 grand. She was like, Well, uh, just so you know, 10 grand, that's just uh that's just a part of my love language being being taken care of financially.

SPEAKER_07

That's her love language, huh? She ran that game over the last season.

SPEAKER_09

She ran, she ran game and I ran away.

SPEAKER_07

That's the thing for you to do, too.

SPEAKER_09

I so what what judgment call for true love?

SPEAKER_07

Hold out for it? It's obvious. Yeah, but definitely not for that nonsense that was going on.

SPEAKER_01

Judgment call.

Parents Confront The 44-Year-Old Boyfriend

SPEAKER_02

Am I the asshole for telling my daughter that her boyfriend isn't welcome in our home? My female 48, husband, male 46, and I have a 20-year-old daughter, Ellie, who is currently on vacation from college. About five months ago or so, Ellie told us that she had a new boyfriend, Tom. This came rather out of the blue as Ellie hasn't mentioned seeing anyone before that she was dating. But both my husband and I were very supportive and happy for her. However, Ellie was strangely secretive about the whole situation. Usually she's an open book, especially with me, and would always share details about her personal life. On this occasion, she wouldn't. On this occasion, she wouldn't show any pictures, and we knew no information about Tom other than that they had met at a party through a mutual friend. Ellie spent the past month of her vacation in her college town, and the plan was always for her to come back this weekend. Ellie asked if she could bring Tom with her for a few days of the trip as they were getting serious, and she wanted him to meet us. Although we mentioned that we barely knew anything about him, Ellie expressed that it would be a great surprise and that we'd love him. Given he's clearly an important part of our daughter's life, we agreed and said we'd look forward to spending the weekend together. Yesterday morning, we went to pick up Ellie and Tom from the airport and drive to our place, and we were shocked. We knew instantly that Tom was much older than Ellie, and he certainly wasn't a college student. I was just in a state of surprise, but didn't want to cause a scene, and I told my husband to do the same. We drove home and it was a frosty journey, which Ellie commented on. When we arrived, my husband point blank asked Tom how old he was. Tom said he was 44. I was immediately disgusted. He's only two years younger than my husband and old enough to be Ellie's father. My husband continued to interrogate him, asking how they met and the whole background. Ellie explained that it was at a party and Tom was there because he's quote unquote well known around the town. And they realized they had a lot in common and hit it off from there. I really didn't want to hear anymore, and my husband told Tom to leave. Ellie shouted and said how unfair it was that we hadn't even given Tom a chance and that he made her happy. Tom could sense the tension and left. And Ellie followed behind him. I texted Ellie to tell her we'd love to see her and come discuss the situation. She asked if Tom was welcome, and I said he wasn't. Therefore, after labeling me a judgmental asshole, she told me that she wasn't coming and that they would be staying at a local hotel and catching up with friends. I feel terrible about the whole situation and don't want to lose my daughter over it. My husband isn't budging and says he'd have to be held back if he ever saw that man again. Am I the asshole for saying he isn't welcome? Or have I done the right thing?

SPEAKER_07

I understand why you say he wasn't welcome, but that's gonna that's not gonna get you what you want. The minute you start pushing them, pushing her away, pushing her away, her whole job will be to go to him, go to him, go to him. You may not like him, you may not want him to be with you, and you may just want to wait, wait for her clock to kick in, like, oh, this this doesn't make any sense. I have enough problems and and issues going, but uh not having them around does exactly the opposite of what you want to have done. That's what I think.

SPEAKER_09

I think you're 1000% correct. Uh Sun Su, the art of war, it is always easier to annex the kingdom than keep someone from storming your castle, right? Yep. You want you want him in your house, you want him to park his feet under your table because you want to explore exactly who this man is, who your daughter is so enamored with.

SPEAKER_07

Right. And you want to be there in case it goes wrong and goes badly, and and and and you want to be there and want to make sure that your daughter feels like she can talk to you if something isn't going right. Because if you already don't like him and they know you don't like him, and he's starting to do things that she doesn't like, she's not gonna tell you because that's more fuel on your fire, that's more support for their position. You gotta stay friends. You be honest how you feel about it, right? But all but but leave the lines of communication open. Right.

SPEAKER_09

And two things can be true. Hey, Ellie, baby girl, what we don't like this age gap situation, we don't feel good about it, but we love you, right? And we're gonna be here for you. Uh, and we're gonna we're gonna figure this out and we're on the ride and we're gonna ride it with you, but you never wanna you never wanna put you never want to set somebody up you love to be in a situation where they're in fear of you coming back and saying, I told you so, if it blows up in your face.

SPEAKER_07

Yeah, right, right, and we're presuming it's gonna blow up, and it may not. Sometimes some relationships, you know, they start out so wrong, they end up right anyway, and you're you're surprised about it, and we don't know enough about you know his motivation and his his experience and his past and hers and all of that kind of stuff. It just looks funny from where we are, right?

SPEAKER_09

Well, and there is no rule that says your love is something that has to make sense to anybody else, it just doesn't right now.

SPEAKER_07

In my divorce court world, I used to find that often when there was a huge gap like that, there was a control issue. Yeah, in other words, I got somebody young and and and manageable and and and going to mold them into what I want. And I've seen that a couple of times, and I've seen parents have concerns over that, you know, as as as they well should. Yeah, but I just don't know enough in this circumstance to say, hey, he's one of those.

SPEAKER_09

Now, if you're out there singleton slugging it out, as some of the younger women will say in their 20s and in their 30s, they will say, Listen, guys, our age are not what we're looking for anymore. Because we out we out educate them three to one, we out-earn them in most cases, and emotionally, we are light years ahead of where they are. So we need somebody with a bit of an age gap to feel like they're on our level, and that's somebody who we can look forward to to learning things from and being with. And so a lot of the younger ladies are saying, yeah, actually, we are looking for those older guys because and now these days, Judge, because they are in more and they are more financially stable, right? They can they can afford, and it's not like we're asking for the world, but they can afford the little piece of it that we want to experience, right? Right, but also it goes so that it's going both ways, yeah.

SPEAKER_07

But I I just hope her parents leave the lines of communication open because they they do not want to become the enemy because they won't have any any role in the conversation, and there will be conversations that need to be made, even if it's a good relationship, there's still issues and problems that you have to deal with simply because he is so much older. You will turn into a caregiver at some point, you know. You understand that, you know, the children, all of that. I mean, it's right, right.

SPEAKER_09

At some point, you will be ordering uh adult depends on Amazon. At some point, that's gonna happen. So listen, and um, what was I gonna say? There is uh the wisdom, the wisdom is always like you said, always leaving those lines of communication open because uh we've seen this a bunch of times. You've had girlfriends, I've had friends, they get into a toxic situation. Everybody in the group knows though, that's probably not gonna end well for you. But if we say that out loud, now we become the enemy. So what we want to do, right? What we want to do is we just want to support it. Hey man, if that makes you happy, go for it. If that's if that's where you are right now, go for it, but leave the door open for them to come back and talk to you if if and when it starts to go left. Leave the door open and be supportive, and then you deliver the message that you're concerned and that you had this.

SPEAKER_07

Absolutely, absolutely. So, judgment call for I don't know, for the is for the young lady hoping that she'll make the right decision and the right and and the right call. Um but uh I don't know enough about him, and the parents need to keep those lines open. But judge, age age gaps, uh it's a thing.

SPEAKER_09

Look, one of my favorite actors right now, Al Pacino, he's 86 years old. Ask me how old his girlfriend is. Go ahead, ask her. How old? How old is it? Oh, she's 33. Yeah. And they and they just welcome the child together into the world.

SPEAKER_07

Well, that's wonderful. No, it is, it's wonderful. I just, you know, it's it's it just yeah.

SPEAKER_09

And there's all the ridicule and the judgment that you would think goes along with it is what they're getting, but to their credit, they're like, hey, this is kind of weird.

SPEAKER_07

Yeah, this is what we're doing. Um Robert Nero was an old father, and and all a lot of a number of them, you know, able to do that. So, you know, and it can't get mad.

SPEAKER_09

It's your love, it doesn't have to make sense to the rest of the world as long as it makes sense to you. So, what do we learn today, Dr.

Fair Exchange, Clear Rules, Closing

SPEAKER_09

Ish? Well, we have learned that um in the purest of terms, there should always be a fair exchange of goods for services rendered. Yikes, I think that sums it up. Well, I think there is something there is there's something to be said for laying your cards out on the table, letting everybody in the room know why you're there and what you're looking for, and then seeing who's looking for the same thing. I tell folks all the time, you don't have to lie to people to get them to, you know, to to to be into you, right? Uh uh as the kids say, you don't have to lie just to kick it. You don't, right? Because you would be amazed how many folks who are in that room with you are looking for the exact type of dynamic that you're looking for. Somebody's just gotta have the guts to say it out loud. And once you find it, now we don't have to find hide things. We don't have to hide the jewelry from our rich exes, we don't have to hide the AIDS from our parents before dinner. We can be what we can be full steam ahead because everybody knows why we're in the car and where we're headed, and the rules of the rules of engagement have been clearly defined, and we're all okay, and we're all obeying them.

SPEAKER_07

Thank you so much, ladies and gentlemen. This is Judgment Call. If you want to have your question answered by us, uh hit us up on Instagram at judgment.call.podcast, and we will answer your questions. We're also looking for you to come on the show if you want to. You and someone else not quite sure how to resolve an issue. We'd love to help you with that. Anything on on that, Dr. Ish?

SPEAKER_09

I think it'd be fun. I am looking forward to having some of our fans of the show come on because you you are like me. We love being in the room working with the people doing the absolutely.

SPEAKER_05

She's seen it all from the bench, he's helped couples through it all. Now they're making the call on the internet's biggest relationship debates. Real relationships, real reactions, real talk. This is Judgment Call.

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