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James Sexton

James Sexton

American attorney

Oct 30, 2026

1:05
One of the interesting things we were talking about before we started filming was it's really uncomfortable to turn to your partner and ask them for a prenup.
1:12
I know a lot of people say that, and I think it's a question of how you enter the conversation.
1:17
Again, like, you know, I guess because I get paid to talk, and I'm used to talking sometimes about difficult things with a judge or revealing, you know, things that are hard to reveal about someone and trying to make sure that they're not viewed negatively, even though they might have behaved negatively.
1:32
So I think prenup, it's all about how you bring up the conversation.
1:35
And my preferred entry point for a prenup when I talk to someone is every single person who gets married has a prenup.
1:43
It's either written by the government or it's written by the two people who love each other more than the other 8 billion people in the world.
1:50
I personally think that the two people in a marriage are better qualified to create the rule set of their marriage than politicians they don't know, especially when you consider the nature of politicians.

12 MINS LATER

14:03
You should have to provide receipts.
7:21
Antes de que sea demasiado tarde.
7:22
Deben ser proactivos e informarse de lo que va a ocurrir legalmente, qué va a pasar con mis derechos, qué va a cambiar en términos de propiedad, las obligaciones financieras que tendré con esta persona.
7:32
También diría que una de las mejores cosas que podrían hacer es hablar con alguien con franqueza que lleve casado mucho tiempo.
7:38
Eso no es algo que hagamos.
7:40
No se nos anima a ser honestos sobre nuestras relaciones.
7:43
No lo hacemos.
7:44
Una de las cosas de las que hablas en Mask of Masculinity, que me encantó, es sobre en particular para los hombres, pero creo que también es cierto para las mujeres.

1 HR 11 MINS LATER

79:07
Tienes un seguro de vida.
0:44
Mm
0:44
... to be honest about our relationships.
0:46
We're not.
0:47
I mean, one of the things you talk about in Mask of Masculinity that I loved is about, uh, particularly for men, but I think it's true for women, too, we don't share candidly what's really going on in our lives.
0:57
We're in a very curated society where you put up on social media the best picture and the best vacation photos and the best of everything we're doing, and we don't share with each other the challenges.
1:10
We don't share with each other even, even really relevant information.
1:14
Like, when I meet a couple who's been together for 20 years, I mean, I love the story.
1:44
Yeah
5:38
Mm-hmm.
5:38
And I, I say that's my job.
5:40
I'm, I'm a shield and a weapon, and I'm a shield in the sense that my job is to protect my clients' interests, and I'm a weapon in the sense that I'm there to advocate what it is that they need me to, to fight for, what it is that they need me to advance.
5:51
I represent people who've been cheated on, and I represent people who cheat, and I represent people who their spouse has a drug or alcohol problem, and I represent people who have drug and alcohol problems.
6:00
So- I've spent so much time with every variety of the person in a couple that that's how the book happened.
6:11
It really turned into...
6:12
You know, look, I'm not a therapist.

42 MINS LATER

48:36
And again, I think if people understood those concepts before they got married or even thought about them-
0:51
I'm an adult man." What's something cheating teaches you that divorce doesn't?
1:00
Oh, that's a really interesting way to ask the question.
1:03
So I think more people cheat than anyone wants to admit out loud.
1:08
I think it's one of those things that, like, no one wants to admit that they eat at McDonald's, and yet they sell billions of hamburgers.
1:15
So someone's eating there, right? Like, so I think people cheat.
1:19
People have been cheating a really, really long time.
1:21
That's why if you believe that God, you know, like spoke through a burning bush and gave us ten rules, two of them were, "Don't cheat." Like, thou shalt not kill got one, but don't cheat got two.

1 HR 54 MINS LATER

115:37
Is that what it was for you?
0:37
With blowjobs and granola
0:37
... it's no problem at all.
0:38
No. It's bl- it's, it's, so blow- bl- this is like, this story blew up.
0:42
So I, I was representing a woman, and she, I'd been a lot of miles with her.
0:47
It was an ugly divorce.
0:48
She was like a successful, you know, finance person in New York City, very put together, two kids, husband who was in finance.
0:56
Husband was kind of a train wreck.

1 HR 17 MINS LATER

77:27
Yeah.
48:02
What about the idea of staying in a marriage for the kids?
48:07
So staying in a marriage for the children isn't something people are actually doing a lot of the time, you know? Because your children are in the marriage with you, and the question is not are their parents divorced.
48:19
They're not gonna remember whether you stayed or not.
48:21
They're gonna remember what your marriage looked like.
48:24
Like, they're watching everything you're doing.
48:26
Like, my dad sat there when I was a kid telling me, "You definitely shouldn't smoke.
48:30
It's bad for you," while smoking a cigarette.

28 MINS LATER

76:11
but they just can't move on, like they're still struggling?
9:27
Mm-hmm.
9:27
Like, in every aspect of my life, personal and professional.
9:30
I'm very quick to apology because it doesn't cost anything, and most of the time, there is something for me to apologize for in almost any interaction.
9:37
Like, I think that there's, it's such a safe move.
9:39
Like, when I get on the phone with a lawyer, I have a lawyer on the other side of a case, and I've never had a case with this person, and they just come at me really hard.
9:47
You know, they just come at me really aggressive.
9:49
I'll immediately say, "You know, I, I know this is our first case together, but, um, just from the way you're coming at me, like, I, if I said something in our initial communication that, like, made you feel like I didn't respect you or that we had to be, like, off at this kind of tone, I'm, I'm really sorry.

20 MINS LATER

30:18
Are you giving anyone the opportunity to demonstrate excellence?
George HahnNARRATOR
15:15
Together, they answered a listener's question on what really ends a marriage.
15:20
You know, I think the biggest predictor of divorce is, is, is something subtle, and that is just disconnection between two people.
15:26
I, I think everybody looks for, like, the big relationship killers, you know, like people who are in open relationships or people who...
15:33
You know, sometimes that's the blood in the water, you know, of the relationship being in distress.
15:37
But I, I think it's actually much more subtle than that.
15:39
I think people get divorced and their relationships fall apart the same way that, uh, I think Thomas Wolfe said, uh, people go bankrupt very slowly and then all at once.
15:48
So I think it's a lot of little, small pieces of disconnection that eventually just catastrophically lead to the failure.
16:02
... can you tell that story?
23:22
Yeah.
23:22
Like, like, an economy is any exchange of value.
23:25
So, like, how many apples is worth apples? That's easy.
23:29
One apple's worth one apple.
23:30
How many apples is worth a pineapple? Okay, well, now we have an economy.
23:34
'Cause, like, an a- a pineapple's bigger.
23:35
It's harder to find.

14 MINS LATER

37:20
Yeah
28:45
Is it true that content couples really don't cheat?
28:50
I don't know that I'm qualified to answer that except to say that most of the couples that I meet, it's because their marriage has catastrophically failed.
28:56
So I don't know that I'm the right sample to answer that for you.
28:59
What I will say is, having been part of the Brazilian jiu-jitsu community for many years, I've spent a lot of time in Brazil.
29:04
And in Brazil, prostitution is legal.
29:07
It's restricted, but it's legal.
29:09
So there are what's called termas, which means spa, basically.

25 MINS LATER

54:26
But
14:14
How do couples preserve both fairness and desire over decades without one undermining the other?" James?
14:20
You know, I, I tend to think we need to be thinking about equity and not equality.
14:25
I think fairness is what's important.
14:26
I mean, I, I've said before when I talk about relationships, "Look, if I love to cook, and you don't like to cook, the, the, the school of thought that says, 'Well, we should do fifty-fifty on the cooking,' okay, so you should spend half the time doing something you don't enjoy, and I should lose half the time doing something I enjoy?" It doesn't make any sense.
14:45
But that being said, you should know how to cook a little bit.
14:48
Like, I'm gonna be away at some point, and you need to, like, do something other than DoorDash.
14:52
Same thing with finances.

13 MINS LATER

27:24
You go first, James.
26:01
Yeah.
26:01
Like, you, you can do that right now.
26:03
Like, you don't have to wait.
26:05
Like, when people have a crisis in their marriage, someone's parent is ill or dies, something horrible happens, there's this shared sense of, "Oh my God," like, "I gotta take care of this person.
26:16
Are they okay?" Like, my partner is, like, going down.
26:19
Like, I need, they need me.
26:21
You don't have to wait.

49 MINS LATER

75:39
[laughs]
7:12
When I was looking for a lawyer, it was, okay, who actually is known to settle? Who's not self-interested in the money? How does one figure that out when they're hiring an attorney?
7:23
yeah i mean gosh there's a lot there to unpack so what i'll say to you is as a trial lawyer who has a reputation as being a very effective sort of weapon in a courtroom what i will tell you is it makes a lot of sense when you're a client and a consumer who's in need of the work that divorce lawyers do to think that the right way to approach it is to hire someone who has a reputation as being settlement-minded and more of a non-aggressive attorney.
7:56
Unfortunately, in my experience, that often results in people ending up more in litigation than not.
8:04
I think it's better to be a warrior in a garden than a gardener in a war.
8:08
It's better to have a gun and not need it than to need a gun and not have it.
8:11
And a trial lawyer is a weapon.
8:13
What you said is absolutely accurate, which is you should never do something with a chainsaw that you could do with a scalpel.

1 HR 11 MINS LATER

Randall KaplanADVERTISER
79:48
as an example.
16:08
What's a divorce budget that somebody should keep in mind, like for a lawyer, forensic accounting?
16:15
That could be tricky.
16:16
You know, people-- The two most reasonable questions anybody can ask me at a consultation is, "How long is this gonna take and how much is it gonna cost?" And I always tell them those are the two questions no honest lawyer can answer, 'cause divorce is like a table with four legs.
16:28
There's you and your lawyer and your spouse and their lawyer.
16:31
If one leg is off, it doesn't matter how nice and straight the other three legs are, [chuckles] the table's gonna fall down.
16:36
Like, and then the next question people say is they go, "Well, give me a range." You know, like, what's the range? Like a easy divorce expense versus a really difficult divorce expense.
16:45
And I always say to people, it's kinda like calling your friend who's a doctor and saying, "I have a headache.

9 MINS LATER

25:23
... show up in an alimony discussion?
5:03
What should they do?
5:03
I think it depends.
5:04
See, I personally, I've represented extremely wealthy people for a really long time now.
5:10
Before that, I represented, you know, regular mom-and-pop type people.
5:14
I ha- I grew up poor, and I didn't have any money.
5:18
College, when I was in university, I worked as a waiter, as a server.
5:22
Um, like I, I had nothing.
10:05
Yes.
15:08
You know, as a kid, you're sitting there every six months experiencing sort of a living loss, which has to be just... tough you know my mom gonna die soon um and then as a result of that at some point you gain 30 pounds which is you as a lot of people do today they manifest their unhappiness in food some people do it shopping so how old were you when you got that weight gain and and did you realize at some point you know what i'm getting heavy this isn't healthy for me and I need to lose it and I really need to change and get my shit together.
15:45
Yeah, I took comfort in food from a very early age and I didn't, I think my mother and father were so occupied with the things that they were dealing with, the alcoholism, the illness, that I didn't really get an education on nutrition.
16:00
So like I would ride my bike down to the store and get like giant bag of Cool Ranch burritos and a big thing of Dr. Pepper.
16:09
And that was like, to me, that was like a perfectly acceptable snack or lunch.
16:13
And so I got very heavy as a kid.
16:15
I was a fat kid.
16:17
And that exacerbated some of my isolation because when you're a fat kid, you know, you're not good at sports.

18 MINS LATER

Randall KaplanADVERTISER
34:23
colder to me and meaner to me.
speaker_2HOST
25:01
Not once, not ever.
25:02
But understanding, like, how to have a conversation with your romantic partner, like the importance of checking in with them, how to tell someone something they don't wanna hear in a way that doesn't make them instantly defensive, like those are really, I think, easy teachable skills.
25:22
Like, how many men...
25:25
I, I will tell you, I've met so many men who one of their chief complaints in their marriage is, "We, we used to have so much more sex, and now we don't have as much sex." And if you say to those guys, "Have you ever brought the topic up?" They'll often say, "Well, yeah." And I'll say, "What did you say?" And they'll say, "I said, 'Hey, why aren't we having sex as much as we used to?'" I'm like, "Did you think that was gonna go well?" Like, that's an accusatory way of bringing that up.
25:48
It's gonna bring out nothing but defensiveness.
25:51
I'm like, "Whereas didn't anybody ever tell you, like, there's another way to have that conversation?" Like, what if you said to her, "You know what, I, happened yesterday? I was driving past that restaurant that we went to on, like, our third date.
26:05
I don't know if you remember it.

6 MINS LATER

speaker_2HOST
31:55
... all of that stuff were not enforceable.
50:38
Mm.
50:39
Like, I was arrogant.
50:41
I was angry.
50:43
I was terrified.
50:45
I was constantly, like, sticking my chest out and being way too prideful and being way too cocky, and sometimes got my ass handed to me.
50:55
I mean, I, I-- I'll tell you a story.
50:59
I don't think I've ever told this story.

16 MINS LATER

66:39
It will get me just like a centimeter closer.
5:36
Have you been noticing that?
5:37
Yeah, I mean, I definitely see those trends.
5:39
You definitely see that the earning capacity and actual earnings of women is going way up.
5:44
And certainly you see, you know, that when people marry, they have different levels.
5:47
People are marrying later in life.
5:49
So people are more established professionally when they get married.
5:52
But what I will say is, and all the statistics bear this out, women tend to date level or up.

42 MINS LATER

47:45
In all of your experience putting that all together, would you say in terms of marriage, divorce, all of this stuff, more money, more problems? Or less money, financial struggle, more problems?
2:02
You're still 12.
2:03
Right.
2:04
And so isn't that a beautiful expression of love? Like, I always tell people when they, they talk about this sort of like, "Oh, well, you're gonna age," and when someone ages, they j- Okay, I have a dog that is 16 years old.
2:18
I got that dog when the dog was four months old.
2:23
What a youth.
2:24
The dog is now deaf, okay? Gets up every morning, tail wagging, can't wait to eat breakfast.
2:29
He's liv- got a great quality of life.
4:14
Mm.
speaker_3ADVERTISER
6:21
See it in action at gendigital.com.
6:24
And it was just this feeling of like, like it's so quiet, you know, and they'll be back.
6:29
But God, it's so quiet.
6:32
And the greatest thing I did for myself.
6:36
And I don't know what pushed me to do it is I just started to create like routines like we live in a world of symbols.
6:44
And what I would do is they would leave and I would make a point of doing all of the laundry of their clothes and washing their sheets.
6:52
And then I would make their rooms like I would put their beds back just right.
8:58
Until you hit the ground.
8:55
So with all of that being said, if, if somebody doesn't know a whole lot about family law, and just, you know, talking to the average person who is maybe thinking about getting married or already is married or maybe is in a struggling marriage, what are some of the biggest mistakes you see people make, whether it's financial or just causing a lot of unnecessary stress and hassle in their lives as maybe they need to navigate a breakup?
9:23
Yeah.
9:24
I mean, you, you named a couple of very different cohorts there that I think all have different situations.
9:29
So if someone...
9:29
I'll, I'll take them in the order that you said.
9:32
So, you know, if someone is not yet married and they're thinking about getting married, of course that, that is the best opportunity to educate yourself.
9:40
You know, most people, by...

8 MINS LATER

17:38
What are some red flags to watch out for if you are dating someone? Is there anything in particular that kind of stands out maybe related to finances, either, uh, not being transparent enough about finances or just not even wanting to have that prenup conversation? Anything there that people should say, "Wait a minute, let's rethink this."
54:52
Now, you, for those listening who might not be familiar with, uh, EDIT, ca- can you just paint a picture of just how stark that difference is between when a child inherits versus when a niece or a nephew inherits under, looking under Irish court law?
55:09
Absolutely.
55:10
And, and that, that is really, really important because it is only when the numbers are presented to your listeners, they will say, "Oh, my God, this is me.
55:21
This is the situation that my loved ones or family members will be faced with when I'm gone." Because their family members, uh, brothers, sisters, nephews or nieces, um, carers, close neighbors, lifelong friends, they will be saddled with punitive inheritance tax bills that simply do not apply to other cit- to other citizens.
55:45
So if we take, for example, uh, this morning, a home in Cork, uh, bought and paid for, uh, by a citizen over an entire lifetime, uh, currently valued at, um, €400,000, and that cit- that person wishes to leave it to their only child upon death.
56:03
Now, that child will thankfully have an inheritance tax bill of zero.
56:08
Now consider the same home valued at €400,000 that a childless citizen wants to leave to, uh, a brother, a sister, a nephew or niece upon death.
60:11
There's lots of other groups who are very much affected by this.
42:11
We also need to have-
42:12
Well, we can agree on that.
42:13
But you, you can't agree that they could reallocate resources to childcare.
42:16
And by the way, to answer your earlier point, what's happening in the European Union, by the way, it, it could be that in various...
42:23
Like Singapore's reasons for not having children versus the United States' reasons for not having children could be dissimilar and don't have to be connected to each other, right? Like the proliferation of cigarette smoking in one country versus another is not a function of now this is global how we're feeling.
42:38
Yes, the birth rates are down in various places, but they might not be down for the exact same reasons.
42:42
When you ask women about what it is that they want, younger women, motherhood is lower on the list now.
45:48
Well, why, why do women ha- who have children have them later in life?

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