Podcast Summary: The JTrain Podcast

Episode: Men Can’t Handle Jokes Michelle Wolf – CHIT CHAT WEDNESDAY
Date: October 22, 2025
Host: Jared Freid
Guest: Michelle Wolf
Theme: Comedy worlds, the realities of being a standup comic, online algorithms, parental judgments, hotel breakfasts, corporate gigs gone wrong, and why men can’t handle jokes.

Episode Overview

This Chit Chat Wednesday episode features comedian and friend Michelle Wolf, whose new special, The Well, is streaming on Netflix. Jared and Michelle riff on the promotional hustle demanded by the streaming world “algorithm,” the pitfalls and pathos of life on the road as a comic, parental culture wars on social media, and the wild misadventures of performing for tough crowds. The episode is light, honest, and deeply funny, filled with break-neck banter, memorable road stories, and meta-commentary on comedy and modern life. They close with a riff game, spinning breaking news into comedy bits.

Key Discussion Points & Insights

The Netflix Promotion & The Tyranny of the Algorithm

[00:55–04:00]

Jared goes meta, opening the show with a plea to watch Michelle’s The Well on Netflix:

“Go turn it on right now. It’s hilarious. It’s spectacular. You’re going to love it.” (Jared, 01:34)
Both joke about pleading with fans just to boost the almighty “algorithm”—not even caring if it’s muted or only for dog-viewing.
Michelle reflects on the absurdity:

“When are we going to admit the algorithm isn’t real?... you made the algorithm, like, you just changed a couple zeros and ones in there…” (Michelle, 02:30–03:01)

Social Media Parenting Judgment

[03:16–06:14]

Jared refers to Michelle as an “expert mom,” sparking a tangent about online mom-shaming.
Michelle describes moms on social media as “riddled with anxiety,” always warning about unsubstantiated dangers.
Jared sees mom-group drama as a metaphor for all internet fights:

“If you do it differently, then you’re somehow saying that...You must inherently think anyone who does it differently than you is a mother murderer, idiot.” (Jared, 04:51)
Michelle’s advice: “Just relax. Just do what works for you. Take a breath and take a nap.” (05:07)

Standup Comedy: “Policies” and Relatable Material

[06:17–08:25]

Jared and Michelle bash hacky airplane and Starbucks jokes, calling them “cheap tricks” for easy audience connection.
Michelle quips:

“If you’re talking about airplanes, you’re not doing enough…you need to do stuff other than standup.” (Michelle, 07:07)
Jared’s “policy”: Save mundane “airplane jokes” for online, not the stage.

Comic Life on the Road: Hotels, Buffets, and the Sad Extended Stay

[10:19–16:17]

They lampoon comedian Todd Barry’s infamous preference for sitting in the middle seat on flights.
The comic’s relationship to hotel breakfast buffets:

“If they have a Greek yogurt…maybe I’ll take that. But I’m never sitting down and getting, like, a waffle…that’s not my jam.” (Michelle, 11:01)
Both discuss “tier badges” for comedians based on what hotels they endure.
Michelle shares her “Red flag” for rooms with kitchens, recalling a night in an extended stay that stank of “a combination of everyone’s food—apple cinnamon and everyone else’s food…so gross.” (15:01–15:27)
Jared distills the comic’s emotional extremes:

“The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)

Google Searches & Awkward Gigs

[17:03–21:59]

Both trade stories about the dumbest things they’ve Googled (“doctor who does butts”).
Michelle: A comic’s life is full of ridiculous searches and stranger gigs.
Jared recounts a traumatizing gig presenting at a urologists’ event—“I got hired by a pharmaceutical company…couldn’t even pronounce the words on the PowerPoint…all I was thinking was, ‘Don’t lose the money!’” (20:10–21:10)
“The problem is you…” Michelle: "I remember when you went to this gig…” (20:05–20:10)

Corporate & Odd Comedy Gigs

[21:34–27:05]

Michelle recounts performing at a corporate dinner with a “fish on ice” theme:

“So I was like, you can’t escape it. It’s either me talking about periods or the fish behind you smelling like them.” (Michelle, 22:53)
On men who can’t handle period jokes:

“[He was] like, I can’t even… How can you not hear the word? What gilded cage do you live in?” (Michelle, 23:27)
Saddest gig: The birthday of a billionaire’s ex-wife, who’s "too rich to laugh," with a crowd rendered inert after a mentalist’s act:

“Everyone was very aware that…we have to make sure she has a good time. This is the first birthday that’s right. Without her husband.” (Michelle, 27:38)

Audience Dynamics & Comedy’s Emotional Highs and Lows

[27:38–29:45]

Jared recounts a bachelorette party “destroyed” because the bride cried, leading to mass walkout.

“At one point, I was like, you guys are taking forever…Their description of the bachelorette party is, like, forever horrific.” (Jared, 28:29–29:29)
Both riff on how disaster becomes legend—for both comics and audience.

“The Well” Comedy Special—Content & Artistic Intent

[30:16–34:39]

Michelle admits she hasn’t fully watched her own special since 2024:

“I know it’s ready, and I know it’s good. But… I just can’t. I can’t watch it again.” (Michelle, 30:48)
Special covers “everything—gay men, Democrats, Republicans, first-time mom stuff” and takes risks.
Michelle:

“The first joke, you may hear it and go, I’m out… but if you’re in after the first joke, you’re in for the whole thing.” (31:19–31:47)
On material: “I’m never actually thinking about the audience. I’m doing the jokes I want to do, and I hope they like them.” (31:47–32:04)

The Old Hairy Back Baby Gift Story

[34:03–36:26]

Jared recounts gifting Michelle’s baby a monogrammed towel (“Old Hairy Back”) after Michelle joked her newborn looked like a “little old man…with hair on his back.”
On being a comic in real life:

“If they believe you’re a comedian…then you’re in this weird valley where you can literally do anything you want.” (Jared, 36:26)

“What’s the Bit?” News Spin Game

[37:45–44:34]

Michelle and Jared take outrageous news headlines and riff on how they’d turn them into stand-up bits.

Example 1:

Headline: Kevin Federline accuses Britney Spears of wishing her kids dead.
Michelle’s take:

“This guy [the son] is not a guy who has to feel guilty about missing holidays…he’s free.” (38:31–39:08)

Jared: Kevin Federline’s life has been the extreme highs and lows—"he’s seen the Four Seasons Hotel and he’s also seen the Hyatt house in the parking lot." (39:37–39:56)

Example 2:

Headline: Why Tom Cruise and Ana De Armas relationship fizzled out
Michelle:

“For me, I would fizzle out because he probably didn’t jump on Oprah’s couch celebrating his love for me…For Katie Holmes you jumped on Oprah’s couch. Her white couch. With your shoes on.” (42:49–43:26)

Jared: “That’s the most female way to look at dating Tom Cruise.” (43:05–43:18)

Notable Quotes & Memorable Moments

On standup comedy:

“Would I tell a room full of people, sit down, shut the fuck up, I got something to say? ...I don’t think a lot of people do that anymore.” (Jared, 08:08)
On the emotional range of a comic’s life:

“The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)
On audience discomfort:

“You’re a grown man living in the world. How can you not hear the word [period]?” (Michelle, 23:27)
On post-conservatorship Britney:

“No one…was like, hey, my bad. Like, no one…was like, okay, maybe free wasn’t the right word.” (Jared & Michelle, 41:40–41:54)
On promoting comedy specials:

“Just put it on in the background. Let your dog watch it. You don’t have to watch it.” (Michelle, 01:55; repeated at 44:36)

Segment Timestamps

[00:00–04:00] – Cold open, promoting The Well, and Netflix algorithm jokes
[04:01–07:07] – Social media parenting wars
[07:08–08:25] – Jokes and “policies” in standup
[10:19–16:17] – Road life, hotel buffets, and sad extended stay hotels
[17:03–21:10] – Weirdest gigs and awkward Google searches
[21:34–29:45] – Corporate, private, and crowd disaster stories
[30:16–34:39] – Comedy special content and artistic authenticity
[34:03–36:26] – The “Old Hairy Back” baby gift story
[37:45–44:34] – “What’s the Bit?”—improvised news riffing

Conclusion

A lively, sharp, and revealing conversation about comedy on and off stage. Jared and Michelle’s chemistry covers the real tensions of making people laugh in 2025: algorithm anxiety, getting shamed by strangers, and the constant search for stories worth telling. If you’re a fan of unfiltered comedy, you’ll love both this episode and Michelle’s special, The Well.

Key takeaways:

Watch The Well—or just play it (for yourself, your dog, anyone)—on Netflix
Embrace your own way of doing things; ignore internet morale
Standup comedy is still brutally honest work, and the best jokes are the riskiest
Bad gigs and hotel breakfasts are comedy gold
Men (sometimes) really, really can’t handle jokes about periods

Listen to the full episode for even more punchlines and storytelling.

Podcast Summary: The JTrain Podcast

Episode Overview

Key Discussion Points & Insights

The Netflix Promotion & The Tyranny of the Algorithm

[00:55–04:00]

Jared goes meta, opening the show with a plea to watch Michelle’s The Well on Netflix:

“Go turn it on right now. It’s hilarious. It’s spectacular. You’re going to love it.” (Jared, 01:34)
Both joke about pleading with fans just to boost the almighty “algorithm”—not even caring if it’s muted or only for dog-viewing.
Michelle reflects on the absurdity:

“When are we going to admit the algorithm isn’t real?... you made the algorithm, like, you just changed a couple zeros and ones in there…” (Michelle, 02:30–03:01)

Social Media Parenting Judgment

[03:16–06:14]

Jared refers to Michelle as an “expert mom,” sparking a tangent about online mom-shaming.
Michelle describes moms on social media as “riddled with anxiety,” always warning about unsubstantiated dangers.
Jared sees mom-group drama as a metaphor for all internet fights:

“If you do it differently, then you’re somehow saying that...You must inherently think anyone who does it differently than you is a mother murderer, idiot.” (Jared, 04:51)
Michelle’s advice: “Just relax. Just do what works for you. Take a breath and take a nap.” (05:07)

Standup Comedy: “Policies” and Relatable Material

[06:17–08:25]

Jared and Michelle bash hacky airplane and Starbucks jokes, calling them “cheap tricks” for easy audience connection.
Michelle quips:

“If you’re talking about airplanes, you’re not doing enough…you need to do stuff other than standup.” (Michelle, 07:07)
Jared’s “policy”: Save mundane “airplane jokes” for online, not the stage.

Comic Life on the Road: Hotels, Buffets, and the Sad Extended Stay

[10:19–16:17]

They lampoon comedian Todd Barry’s infamous preference for sitting in the middle seat on flights.
The comic’s relationship to hotel breakfast buffets:

“If they have a Greek yogurt…maybe I’ll take that. But I’m never sitting down and getting, like, a waffle…that’s not my jam.” (Michelle, 11:01)
Both discuss “tier badges” for comedians based on what hotels they endure.
Michelle shares her “Red flag” for rooms with kitchens, recalling a night in an extended stay that stank of “a combination of everyone’s food—apple cinnamon and everyone else’s food…so gross.” (15:01–15:27)
Jared distills the comic’s emotional extremes:

“The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)

Google Searches & Awkward Gigs

[17:03–21:59]

Both trade stories about the dumbest things they’ve Googled (“doctor who does butts”).
Michelle: A comic’s life is full of ridiculous searches and stranger gigs.
Jared recounts a traumatizing gig presenting at a urologists’ event—“I got hired by a pharmaceutical company…couldn’t even pronounce the words on the PowerPoint…all I was thinking was, ‘Don’t lose the money!’” (20:10–21:10)
“The problem is you…” Michelle: "I remember when you went to this gig…” (20:05–20:10)

Corporate & Odd Comedy Gigs

[21:34–27:05]

Michelle recounts performing at a corporate dinner with a “fish on ice” theme:

“So I was like, you can’t escape it. It’s either me talking about periods or the fish behind you smelling like them.” (Michelle, 22:53)
On men who can’t handle period jokes:

“[He was] like, I can’t even… How can you not hear the word? What gilded cage do you live in?” (Michelle, 23:27)
Saddest gig: The birthday of a billionaire’s ex-wife, who’s "too rich to laugh," with a crowd rendered inert after a mentalist’s act:

“Everyone was very aware that…we have to make sure she has a good time. This is the first birthday that’s right. Without her husband.” (Michelle, 27:38)

Audience Dynamics & Comedy’s Emotional Highs and Lows

[27:38–29:45]

Jared recounts a bachelorette party “destroyed” because the bride cried, leading to mass walkout.

“At one point, I was like, you guys are taking forever…Their description of the bachelorette party is, like, forever horrific.” (Jared, 28:29–29:29)
Both riff on how disaster becomes legend—for both comics and audience.

“The Well” Comedy Special—Content & Artistic Intent

[30:16–34:39]

Michelle admits she hasn’t fully watched her own special since 2024:

“I know it’s ready, and I know it’s good. But… I just can’t. I can’t watch it again.” (Michelle, 30:48)
Special covers “everything—gay men, Democrats, Republicans, first-time mom stuff” and takes risks.
Michelle:

“The first joke, you may hear it and go, I’m out… but if you’re in after the first joke, you’re in for the whole thing.” (31:19–31:47)
On material: “I’m never actually thinking about the audience. I’m doing the jokes I want to do, and I hope they like them.” (31:47–32:04)

The Old Hairy Back Baby Gift Story

[34:03–36:26]

Jared recounts gifting Michelle’s baby a monogrammed towel (“Old Hairy Back”) after Michelle joked her newborn looked like a “little old man…with hair on his back.”
On being a comic in real life:

“If they believe you’re a comedian…then you’re in this weird valley where you can literally do anything you want.” (Jared, 36:26)

“What’s the Bit?” News Spin Game

[37:45–44:34]

Michelle and Jared take outrageous news headlines and riff on how they’d turn them into stand-up bits.

Example 1:

Headline: Kevin Federline accuses Britney Spears of wishing her kids dead.
Michelle’s take:

“This guy [the son] is not a guy who has to feel guilty about missing holidays…he’s free.” (38:31–39:08)

Jared: Kevin Federline’s life has been the extreme highs and lows—"he’s seen the Four Seasons Hotel and he’s also seen the Hyatt house in the parking lot." (39:37–39:56)

Example 2:

Headline: Why Tom Cruise and Ana De Armas relationship fizzled out
Michelle:

“For me, I would fizzle out because he probably didn’t jump on Oprah’s couch celebrating his love for me…For Katie Holmes you jumped on Oprah’s couch. Her white couch. With your shoes on.” (42:49–43:26)

Jared: “That’s the most female way to look at dating Tom Cruise.” (43:05–43:18)

Notable Quotes & Memorable Moments

On standup comedy:

“Would I tell a room full of people, sit down, shut the fuck up, I got something to say? ...I don’t think a lot of people do that anymore.” (Jared, 08:08)
On the emotional range of a comic’s life:

“The happiest is sold out show, fun show. The saddest is way sadder than the happiest could ever be.” (Jared, 16:17)
On audience discomfort:

“You’re a grown man living in the world. How can you not hear the word [period]?” (Michelle, 23:27)
On post-conservatorship Britney:

“No one…was like, hey, my bad. Like, no one…was like, okay, maybe free wasn’t the right word.” (Jared & Michelle, 41:40–41:54)
On promoting comedy specials:

“Just put it on in the background. Let your dog watch it. You don’t have to watch it.” (Michelle, 01:55; repeated at 44:36)

Segment Timestamps

[00:00–04:00] – Cold open, promoting The Well, and Netflix algorithm jokes
[04:01–07:07] – Social media parenting wars
[07:08–08:25] – Jokes and “policies” in standup
[10:19–16:17] – Road life, hotel buffets, and sad extended stay hotels
[17:03–21:10] – Weirdest gigs and awkward Google searches
[21:34–29:45] – Corporate, private, and crowd disaster stories
[30:16–34:39] – Comedy special content and artistic authenticity
[34:03–36:26] – The “Old Hairy Back” baby gift story
[37:45–44:34] – “What’s the Bit?”—improvised news riffing

Conclusion

Key takeaways:

Watch The Well—or just play it (for yourself, your dog, anyone)—on Netflix
Embrace your own way of doing things; ignore internet morale
Standup comedy is still brutally honest work, and the best jokes are the riskiest
Bad gigs and hotel breakfasts are comedy gold
Men (sometimes) really, really can’t handle jokes about periods

Listen to the full episode for even more punchlines and storytelling.

Men Can’t Handle Jokes Michelle Wolf - CHIT CHAT WEDNESDAY

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Summary

Podcast Summary: The JTrain Podcast

Episode Overview

Key Discussion Points & Insights

The Netflix Promotion & The Tyranny of the Algorithm

Social Media Parenting Judgment

Standup Comedy: “Policies” and Relatable Material

Comic Life on the Road: Hotels, Buffets, and the Sad Extended Stay

Google Searches & Awkward Gigs

Corporate & Odd Comedy Gigs

Audience Dynamics & Comedy’s Emotional Highs and Lows

“The Well” Comedy Special—Content & Artistic Intent

The Old Hairy Back Baby Gift Story

“What’s the Bit?” News Spin Game

Example 1:

Example 2:

Notable Quotes & Memorable Moments

Segment Timestamps

Conclusion

Summary

Podcast Summary: The JTrain Podcast

Episode Overview

Key Discussion Points & Insights

The Netflix Promotion & The Tyranny of the Algorithm

Social Media Parenting Judgment

Standup Comedy: “Policies” and Relatable Material

Comic Life on the Road: Hotels, Buffets, and the Sad Extended Stay

Google Searches & Awkward Gigs

Corporate & Odd Comedy Gigs

Audience Dynamics & Comedy’s Emotional Highs and Lows

“The Well” Comedy Special—Content & Artistic Intent

The Old Hairy Back Baby Gift Story

“What’s the Bit?” News Spin Game

Example 1:

Example 2:

Notable Quotes & Memorable Moments

Segment Timestamps

Conclusion