Stavvy’s World #153 – Caleb Hearon
November 3, 2025

Main Theme & Purpose

In this lively episode, comedian and host Stavros Halkias is joined by returning guest Caleb Hearon for a loose, hilarious, and deeply relatable conversation. Together, they reflect on their changing lives as comedians with newfound success, class/status anxieties, Midwest and Baltimore upbringings, the meaning of being a "man of the people," relationships, queerness, grief, and the importance of being a good hang. As always, they answer listener voicemails with compassion, absurdity, and honesty.

Key Discussion Points & Insights

1. From Humble Beginnings to (Temporary) High Society

[02:21 – 09:42]

• Caleb jokes about how much Stavros' circumstances have upgraded since his last visit, from a “cracked den” with “rats in leather jackets” to a posh apartment with a doorman.
  • Caleb: “The last time I did the podcast, I showed up to a cracked den... three rats in leather jackets twirling chains." [03:07]
  • Stavi admits to subletting a rich man’s fancy apartment and "cosplaying as a wealthy captain of industry,” yet feels like an outsider in such rich spaces.
  • Discussion about imposter syndrome, feeling out of place among generational wealth:
    • Stavi: “Any rich space is a space of evil... These people are fucking stupid. Nobody here deserves to be here.” [08:46]
  • They joke about finding Nancy Pelosi memorabilia in the trash, emphasizing the bizarre perks of wealth.
• The feeling of “not supposed to be here,” whether in fancy apartments or among Ivy League types.
  • Caleb shares his insecurity about entering elite spaces as a state school kid during a New York internship.

2. Success, Class Guilt, and Staying "Relatable"

[09:43 – 15:10]

• Both comedians reflect on their financial success and upward mobility.
  • Stavi: “We both... hit the lottery. Each generation, there is a fat straight and a fat gay that get to win, and it happens to be us—white division, by the way.”
• Jokes about their “destined” lives: running family restaurants or Midwest craft stores; how comedy upended those paths.
• Candid talk about buying a loaded RAV4, test-driving luxury SUVs as a bigger guy, and the class contradictions.
• The comic side of still feeling like working-class people even amid success.

3. Cracking the Code of Privilege

[11:33 – 16:51]

• Caleb’s experience as one of a handful of state school kids at an otherwise Ivy League internship:
  • “I talked to five [Ivy Leaguers] and realized, oh, everything I thought about the world is wrong. These people are not smarter than me... They're not special. They just wound up at this better place.” [12:35]
  • The lengths they took for opportunities (“I had a full LinkedIn, DMing people for informational interviews”).
  • The class dynamics of internships designed for those who can afford to work without pay.

4. Dreams of Alternate Lives & Comedy Roots

[18:05 – 25:25]

• Imagining alternate “hometown” lives if comedy hadn’t worked out: running the Greek restaurant/Joanne’s Fabrics/drama club.
• Stavi and Caleb reminisce about their early years—the pivotal moments of choosing comedy over “regular” jobs.
• Heartfelt jokes about humble lives actually being rewarding: “You're poor in the bank, but you’re rich in the soul, you know? Fully, that does sound pretty good.” [21:30]

5. Middle/High School Memories: Assembly Trauma

[27:45 – 31:10]

• Memories of anti-drunk-driving school assemblies: staged crashes, grim reaper mascots, and sledgehammer fundraisers.
  • Caleb: "They would have your classmate splayed out by the car and the mom and dad weeping—the whole school would watch." [28:25]
• The casual normalization of drinking and driving in their hometowns.

6. Youthful Relationship Fails and the ‘Friend Zone’

[33:11 – 38:37]

• Sharing painfully funny stories of romantic awkwardness.
  • Stavi: "My most pathetic one that actually worked was, ‘Want to come back and have some fruit salad?’...” [38:16]
  • Caleb’s legendary “four goodbye hugs” date. Both express how much they’ve grown—and still relate to youthful insecurity.
• The “long game” of hoping for attention via friendship—a dynamic echoed for both straight and gay teens.
  • Caleb: “Don’t spend your time wanting people who cannot or will not want you back.” [35:47]
  • Stavi: “For you, it was a different orientation; for me, it was just that I was that unfuckable.”

7. Coming Out, Sexual Experimentation, and Desire

[39:10 – 44:23]

• Caleb jokes about his Facebook “coming out as bi,” friends’ reactions, and how much it meant.
  • “To be so, like, sure of it... I told my cool aunt I was bi, and she just went: ‘Okay.’” [39:42]
• Stavi muses about possible sexual openness (“If a feminine enough man wants to suck me off and the vibes are right...”)
• Discussion about “size queens,” body aesthetics, and sexual preferences.
  • Caleb: “Dick size doesn’t matter to me... In fact, I don’t like a dick that’s too big... It starts to affect my next day.” [42:00/43:19]
  • Stavi: “This is the kind of bipartisan... reaching across the aisle we need—the gay community, the straight community: Down with huge dicks.” [46:33]

8. The Art of Being a Good Hang

[48:01 – 49:38]

• Why can’t everyone just be cooler?
  • Caleb: “I feel in you, and I recognize in myself—I'm like, I can get along with anybody, and I’m pretty unbothered. Why can’t everyone just be cooler?” [48:14]
  • Stavi attributes it to being “hangout-focused guys”—the lost art of just being a good hang—crediting unsupervised, working-class upbringings for their social skills.
• Lamenting how social media has made people less able to hang and connect—everything feels “sucks dick, dude.” [52:28]

9. Advice Segment – Voicemail Highlights

a. Open Relationship Nerves

[59:44 – 66:12]

• Caller: 21, girlfriend encourages sex with other women if emotionless—she’d even like to watch.
  • Caleb: “Basically, I’m dating the coolest girl in the world, but I’m scared.” [61:49]
  • Stavi: “This is a gift from God... Unwrap it, man. Open Pandora’s box—nothing bad happens.” [62:11]
  • Advice: Enjoy it while you can; you’re young, it probably won’t last, but go for it.

b. Divorce, Identity, and Boundaries

[66:20 – 77:48]

• Caller: Getting divorced after discovering (via gaslighting, drugs, cross-dressing, and pegging) her husband’s hidden life. Feeling shamed for not being “into it.”
  • Caleb: “No, you don’t have to be into pegging your husband in a bra and panties. Of course not.” [70:35]
  • Stavi emphasizes compassion for both parties: “Give her a little venom for a while, but in the end, move on. He’s an opioid addict/cross-dresser in Oklahoma—not an easy guy to be.” [75:54]
  • They praise sexual open-mindedness, but validate choosing your own boundaries.

c. Surrounded by Death—Am I Cursed?

[78:59 – 86:39]

• Caller: 28, immense loss—family, friends, multiple deaths.
  • Caleb: “Sometimes you just have to be sad… But…if you wake up able to move your own body in a house…with clean water… you are like, the top 1% of people who have ever lived.” [85:29]
  • Stavi: “You are not cursed—statistically, some people have awesome lives… some people have bad shit happen to them.” [82:20]
  • Advice: Seek therapy, show yourself grace, and try to live well in honor of those lost.

d. The Return of Bush

[89:36 – 93:09]

• Caller (from the queer PNW): Is “the bush” back? What’s the cis/straight read on pubic hair?
  • Stavi: “It does feel like Bush is having a huge moment… at least you know, I’ve heard rumors... the bushometer is trending towards full bush.” [91:43]
  • Caleb: “I've always found it weird when someone has a problem with pubic hair…”
  • Both agree: Preferences are personal, but demanding a partner’s grooming style is weird. “Let’s find out on the day.” [93:09]

e. Ethical Mischief with an Ex’s Boyfriend

[95:37 – 100:57]

• Caller: Should I pay my ex’s new boyfriend’s felony hit-and-run fine a dollar at a time to mess with them?
  • Stavi: “Absolutely, this is insane. You need to f***ing move on. You’re helping him!” [99:47]
  • Caleb: “He already got his. He hit and ran. You need to move on.” [97:00]

Notable Quotes & Memorable Moments

• “Each generation, there's a fat straight and a fat gay that get to win this lottery, and it happens to be us. White division, by the way.”
  — Stavi [05:56]

• “I want to hug this guy so bad.”
  — Caleb, responding to the ‘Am I cursed?’ caller [81:22]

• “If you wake up able to move your own body…you are like the top 1% of people who have ever lived.”
  — Caleb [85:29]

• “This is the kind of bipartisan... reaching across the aisle we need: the gay community, the straight community—down with huge dicks.”
  — Stavi [46:33]

• “Let’s not kid about the angles. There’s a lot of angles and folds there.”
  — Caleb [94:21] (on fat guys trying to shave their balls)

• “You have to stop. You have to fully move on or you’re insane. This is fucking crazy.”
  — Stavi [99:39] (about stalking ex’s new man’s legal records)

Timestamps for Key Segments

• [02:21] — Show proper begins, discussing class mobility & impostor syndrome
• [08:53] — "Nobody here deserves to be here" in high society
• [12:35] — Caleb’s Ivy League internship social experiment
• [18:05] — Alternate universe: local crafts store, drama club leader
• [28:25] — Drunk driving high school assemblies
• [33:11] — Long game romance and being “friend-zoned”
• [38:16] — “Want to come back and have some fruit salad?”
• [39:42] — Coming out “as bi” on Facebook
• [42:00] — On sexual preference and big dicks
• [46:33] — “Down with huge dicks”— bi/straight solidarity
• [48:14] — "Why can't everyone just be cooler?"
• [61:49] — Voicemail: Open relationship nerves
• [70:35] — Voicemail: Cross-dressing, divorce, and sexual boundaries
• [78:59] — Voicemail: “Am I cursed?”—Excessive loss and grief
• [89:36] — Voicemail: Return of “the bush”
• [95:37] — Voicemail: Ethical schadenfreude/pranking your ex

Tone & Style

The episode is brash, warm, self-mocking, and honest—the comedians are quick-witted, compassionate, but never precious. Expect plenty of absurd tangents, vulnerable admissions, and vulgar (often touching) insight. Both hosts deploy humor to explore deeper social themes, from class/status and queerness to generational trauma and the value of being a real, decent hang.

Perfect For...

• Fans of irreverent, heartfelt comedy
• Listeners wrestling with class guilt, impostor syndrome, or upward mobility
• Anyone in their 20s–30s dealing with relationship ambiguity, grief, or the search for "realness"
• Queer listeners, and anyone interested in honest talk about sex, boundaries, and identity
• People who just want to laugh at stories of youth, bad dates, and the struggle to “make it”

Listen for: Jokes at the expense of AI, class privilege, “Midwestern sensibility,” and Ethan’s (Eldis’s) AV skills. Takeaways: Life is absurd, losses are inevitable, but being a good hang never goes out of style.