The JTrain Podcast
Episode: Girl Dinner vs Steakhouse Dad with Jon Gabrus – CHIT CHAT WEDNESDAY
Date: January 7, 2026
Host: Jared Freid
Guest: Jon Gabrus
Episode Overview
In this lively “Chit Chat Wednesday” installment, Jared Freid is joined by comedian Jon Gabrus for a hilarious, wide-ranging conversation covering life changes, comedic frustrations, midlife hobbies, and, in a delicious finale, a spirited debate over the perfect meal at Hillstone. With their signature candid rapport, Jared and Jon bounce between nostalgia, self-improvement, comedy careers, and what it means to reconnect with the joys (and pitfalls) of adulthood. If you love the banter of two comics balancing vulnerability and humor, this episode delivers.
Key Discussion Points & Segments
Settling Into New Phases of Life
- Jared’s Move to Florida: Jared opens up about relocating to Delray Beach and the freedom of not following the traditional New York/LA comedy path.
- [01:44] “My whole life has moved…Why would I wait? I walked along the beach today. Why would I wait?” – Jared
- Jon’s Reflections on Living Well: Jon shares the appeal of prioritizing happiness and questioning old routines, especially as both enter middle age.
- [04:08] “Why the fuck am I paying this much for rent in West Hollywood when I could fly anywhere?”
| Timestamp: [00:38]–[06:23]
Comedy, Competition, and the “Happy Gilmore 2” Rant
- Feeling Overlooked in Comedy: Both lament how projects like Happy Gilmore 2 cast celebrities or pop stars over working comics, making it harder for improv/stage talent to break in.
- [10:18] “A property that I loved growing up was bad. Was not as funny as... It sucked. It sucked. I'll say it. No offense to the Sandman...” – Jared
- [12:17] “Stunt casting shit drives me fucking crazy. It's like a chance for comedy people to make a... Back in the day, like, I always use 40-Year-Old Virgin, having Jonah Hill come in at the end... Now that one scene would just go to, like, Billie Eilish.” – Jon
- Where Are the Real Comedy Launchpads?: The comics commiserate about tasteless guest appearances and the missed opportunities for actual comedians.
| Timestamp: [09:15]–[16:27]
Returning to Joy: Hobbies, Learning, and “Off Phone” Escapes
- Jon’s Spanish Immersion in Oaxaca: Jon takes a Spanish/surfing retreat to reconnect with youth and mental challenges, describing his ongoing quest to become bilingual.
- [16:45] “I went for a surf and Spanish program...full-blown like midlife crisis retreat trip.” – Jon
- [18:29] “This is my moving to Florida.”
- Hobbies as Adult Coping: Both reflect on the appeal of rediscovering hobbies from their 20s to ward off burnout and monotony.
- [18:42] “I'm kind of right now at the store browsing things I want to do to get off my phone.” – Jared
- Golf as the Dads’ Dungeons & Dragons: Jared elaborates on golf as an all-consuming but comforting ritual, especially without the traditional family obligations.
| Timestamp: [16:27]–[22:13]
Comic Observations on Family, Friends, and Modern Adulthood
- Baby Moon Absurdity: Jared’s run-in at a San Diego golf course with men on "baby moons" sparks a rant about modern fatherhood.
- [23:00] “I was like, I didn't know this was even on the menu for things you're allowed to do.” – Jared
- [23:14] “I rarely say this phrase, but what the fuck? Patriarchy.” – Jon
- Kidless Men as “Threats” to Dads: They explore how their freedom unnerves friends caught in the grind of parenthood.
- [24:30] “Men with no kids are kind of like a guy with kids' worst nightmare.” – Jared
- [24:42] “Nothing makes a person with kids more threatened than someone their age without kids going, like, yeah, well, I'm in Mexico for two weeks alone.” – Jon
| Timestamp: [22:13]–[26:01]
Parents, Technology, and the Everlasting Burden of IT Support
- Comedic Family Tech Fails: Both riff on the agony of helping parents with streaming services.
- [26:31] Jon’s story: “My mom famously called my brother... 'How do I know if my television is on?'... She goes, 'but it seems like it's on.' My brother's like, I cannot even begin to wrap my head around how to explain this to you.”
| Timestamp: [26:01]–[28:22]
The Allure and Irritation of “Florida Living”
- Beach Culture, Ruined by Crowds: Jared and Jon both love Florida but are conscious of its culture and sometimes its denizens.
- [28:50] “Florida, much like everything else in my life that I like, is ruined by the other people who like it.” – Jon
- Adapting to Local Culture: Jared admits he stays quieter in public spaces, reflecting on how social codes shift regionally.
- [29:59] “I stay way more quiet here in public spaces than I would in New York.”
| Timestamp: [28:22]–[30:09]
The Hillstone Menu Game: “Girl Dinner” vs “Steakhouse Dad”
Signature Segment
- Premise: Jared and Jon each construct a hypothetical five-item shared meal at Hillstone, revealing deep personality insights through food preference.
- Steakhouse Dad Mode (Gabrus’s Order):
- Key Lime Pie (“one of the few desserts I love”)
- USDA Prime Hawaiian Steak (“never heard of this, let’s try”)
- Steakhouse Salad
- Chilled Jumbo Shrimp
- Grilled California Artichokes (“limited availability”)
- Deviled Eggs (subbing out salad, for nostalgia and flavor)
- [37:31] “Deviled eggs...with grandma Ding's pickle relish. You tell me Grandma Ding makes her own pickle relish, then I'm in.”
- Girl Dinner Mode (Jared’s Order):
- Spinach & Artichoke Dip (“if you don’t get the spinach and artichoke dip, did you really go to Hillstone at all?”)
- Grilled California Artichokes (agrees on “limited availability” magic)
- Osaka Style Pressed Sushi
- Fries (well done)
- Coconut Shrimp Roll
- [40:44] Jon: “Now your theme almost seems like the meme hashtag girl lunch. And I would be equally happy to sit down for girl lunch with you and just say to each other, life is about this and yap.”
- Personality Shines Through: The segment becomes an unexpectedly incisive character study—Jon takes a classic “steakhouse bros” approach, Jared an adventurous “girl dinner” one.
- [38:08] “This is me reading your palm.” – Jared
- Shared Appreciation: Both embrace the joy of partnership in ordering and the unspoken rules of menu risk-taking.
| Timestamp: [31:18]–[41:39] | Must-listen segment: [34:05]–[41:39]
Notable Quotes
-
Self-Assessment in Comedy:
“I don't think it's happening, like the million dollar job. I don't think it starts happening in your 50s. So I'm happy with where I'm at.”
— Jon [06:23] -
On Stunt Casting and Comedy:
“Now that one scene would just go to, like, look who we got. It's fucking Billie Eilish...That could have been... We know a thousand people who could handle one comedy scene.”
— Jon [12:17] -
On the Joy of Learning Spanish:
“I love to travel... And I was like, oh, I'm enjoying this trip so much more having been able to speak a little bit of Spanish. And I'm like, fuck it, I'm going for it. I want to be bilingual.”
— Jon [17:40] -
Ordering Philosophy:
“You did...you went steakhouse bros. Like, that's the theme of this...You had a theme, which I really appreciate. Because I didn't see it that way at all.”
— Jared [38:08] -
On the Significance of Food Choices:
“If you go to Hillstone and you don't get the spinach and artichoke dip, did you really go to Hillstone at all?”
— Jared [39:10]
Memorable Moments
- “Happy Gilmore 2” Mini-Rant: Joint outrage over lackluster sequels and comedy industry gatekeeping. [09:15]–[16:27]
- Spanish Language Journey: Jon’s delight in “getting off the phone” via immersive learning. [16:45]–[19:02]
- Emotional Menu Analysis: Multi-layered playfulness and seriousness in the Hillstone game, revealing both comics’ approach to life’s pleasures and compulsions. [34:05]–[41:39]
Closing
The episode is a master class in comic chemistry, deftly weaving jokey complaints, honest life discussion, and culinary geekery. Listen for the easy rhythm between Jon and Jared as they explore the theme of living well, whether through new places, new skills, or very opinionated shared meals.
[Listen to the full episode for all the laughs and insight, especially the Hillstone menu debate (34:05–41:39)]