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Modern Wisdom

James Sexton, Rick Glassman, Matt McCusker - Mostly Wise #4 - #1156

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Original episode
PodcastModern Wisdom
Publisher/creatorChris Williamson
Published
Shortcast updated

About this episode

In the fourth episode of Mostly Wise, we explore:

If there is any sexual tension between clients and divorce lawyers.

Why Rick can't hook up with someone he isn't in love with.

Where all the hot goth girls up and disappeared to.

The craziest clauses found in James' clients' prenuptial agreements.

How to talk to your partner about gaining weight.

Gen Z's big problem with being the most sexless generation.

And much more...

Guests

James Sexton is a New York-based divorce attorney and author, known for his expertise in family law and insights on marriage and divorce.

Matt McCusker is a comedian, writer, author and podcaster.

Rick Glassman is a comedian, actor, and podcaster.

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Extra Stuff:

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Episodes You Might Enjoy:

#577 - David Goggins - This Is How To Master Your Life: ⁠lnkfi.re/SN-Goggins⁠

#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠lnkfi.re/SN-Peterson⁠

#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠lnkfi.re/SN-Huberman⁠

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Episode summary

This AI-generated Shortcast summary may omit nuance. Use the original episode when context or exact wording matters.

I’m apparently the granola-and-blowjobs divorce lawyer now. A client’s husband secretly burned huge bonus money in Vegas, but she felt the marriage end when he stopped replacing her yogurt granola. It wasn’t cereal. He used to notice her without being prompted, and that made her feel loved.

Or she could’ve said, “Hey, we’re out of granola.” The gesture matters, but waiting for mind-reading is a game. Though this guy was probably too busy having a Vegas weekend to notice the pantry.

Asking is healthy, but once you request it, it lands differently. She’d stopped doing an unasked-for thing that made him feel desired. Neither was owed; they were small signs of attention. That was the warning flare: granola in the coal mine.

You’ve seen relationships go nuclear, so divorce-level honesty on a first date almost makes sense. But bringing up a prenup that early sounds like opening a spreadsheet over appetizers.

Romance isn’t a transaction, but relationships have an economy: what do we bring, need, and call safety? A prenup is two people writing rules together instead of letting government decide later. If a marriage ends in separation, I want both people protected from economic devastation.

I prefer the zero-to-one-hundred model: my lady, take everything. Economics has no business getting its dry little hands on love. My murder-a-cheater exception was a joke, with an extremely long cooling-off period.

There’s no jury in divorce court, just one judge to persuade. Great lawyers learn that judge’s style, but I hate reducing cases to appearances. They should turn on credible facts, not somebody’s shoes or my stubble.

You don’t feel guilty flattening somebody because each side gets its best case. It’s like an MMA cage, not randomly picking on someone: everybody knows the rules, and the judge stops it.

I believe in proof, admissible evidence, confrontation, and advocacy within boundaries. I don’t need my client to be a saint. Strong facts beat smoke and mirrors. But earn the right to go hard: start gently, get commitments, then expose evasiveness or lies.

Casual sex gave me useful data. Sometimes it was fun; sometimes I couldn’t stay present, and pressure made it worse. I don’t need love or a relationship, but I need to like the person, feel safe, and want to hang out afterward. Otherwise it feels obligatory.

I think about it less spiritually: don’t turn your boner into a board meeting. But he’s asking whether he wants that connection, not whether somebody can make him hard. Mine has offered worse judgment, like a tongue demanding sugar.

Connection is the thing, in sex, friendship, or sitting here. Casual can be great if it’s chosen: yeah, steak and cake tonight. I just don’t want sex, food, or porn to cover loneliness. Notice whether you’re hungry or merely standing at the fridge.

We started as losers making each other laugh. I was thirty, on an air mattress, making peace with being the weird uncle. We weren’t trying to look impressive; we cracked each other up, and people liked being in the room.

Everybody is curating an advertisement now. Your thing feels like friends messing around while we happen to be invited. It may be curated, but it doesn’t feel like you’re begging for admiration. People are hungry for that authenticity.

Politics becomes a weird relationship test. A listener agrees with his fiancée on kids and where to live, but hides political views to avoid fights. Disagreement becomes a verdict on whether you’re morally fit to love.

My parents had radically different politics for fifty years, but shared commitment to family. Now it’s, “You disagree, therefore you’re monstrous.” Understanding fear, dishonesty, or the need to feel seen isn’t endorsing every claim; it’s finding the human need underneath.

Resentment is nasty. I’d rehearse how my wife was wrong, getting hotter in a story she wasn’t there to answer. Counseling helped me see that a garage reminder hit my fear that I was failing her, not the actual garage.

That’s romantic: under the anger is, “I want to be good at loving you.” Anger feels stronger than sadness, but sadness is often there. Skip the scorecard. Notice changes—in sex, health, routines, attraction—and say them before they become fifty-pound problems.

Comedy has the same context problem: a live joke grows from earlier takes, but a clipped line online has none of that trust. And now shows repeat everything for distracted viewers. Still, take harmless wins: a perfect door close, parking as the song ends, every movie line. And boys, solidarity with small asses.

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