So True with Caleb Hearon – "Carly Kane Returns"

Episode Air Date: August 28, 2025
Guest: Carly Kane
Host: Caleb Hearon
Podcast Network: Headgum

Overview

This week on "So True," comedian Caleb Hearon welcomes back close friend and comedian Carly Kane for another round of candid, meandering, and hilarious conversation. The episode dives deeply into customer service horror stories, the psychics and ghosts that haunt queer apartments, the fragile boundaries of queer friendship, memorable restaurant jobs, weird management, and the urgent, communal yearning for autumn. It is both tender and frequently unhinged, with both friends riffing on vulnerability, boundaries, and the chaos of being gay, alive, and just trying to “sort it all out.”

Key Discussion Points and Insights

1. Customer Service Nightmares & Work Trauma

[00:55–04:35]

• E-bikes & Customer Service Despair: Carly vents about the NYC heat and the frustration with electric bikes that won’t dock; both commiserate over how customer service has gotten worse, especially at giants like Verizon and Citi Bike.
• Caleb on Customer Service Jobs: He recounts working as a senator’s receptionist for Claire McCaskill, referencing hostile, sometimes bizarre, constituent calls.
  • "People would call and they'd be like: 'That dumb—' and I'd be like, 'Okay, we're not gonna do that.'" – Caleb [03:10]
• Restaurant and Pharma Customer Service: Carly describes working at a pharma company and how fraught calls about medication were. Both agree restaurant work was more traumatic but yielded wilder stories.

2. Queer Friendship and Touch Boundaries

[04:41–08:16]

• Flirting and Boundaries: Carly jokes about flirting with gay men at her tables and playfully needling Caleb for not accepting her playful touches:
  • "The minute I try to flirt with you, you're like: 'No touching! Boundaries!'" – Carly [05:00]
• Coffee Shop Vulnerability: Caleb shares an unusually vulnerable moment with Carly in a coffee shop, which is instantly derailed by a fan interrupting to say hi, making him feel exposed.
  • "I was being uncharacteristically, like, raw... I feel sometimes like more of an idea than a person lately." – Caleb [06:03]
• Touch Starved Friends: Caleb jokes about having a “type”: lesbians who are touch-starved, feral, and insane. Carly admits she can’t fully relate but, “I understand.” [08:16]

3. Tattoos, Cultural Symbols, and Language Fantasies

[08:29–11:57]

• Painful Tattoos: Carly recounts getting a shin tattoo in Hartford while shoeless and how the pain made her claw up the plastic on the chair.
• Swastika Story: Unpacks how cultural ignorance led a college friend to get a swastika tattoo, supposedly as a Buddhist symbol.
• Languages: The duo discusses which languages they'd like to magically acquire:
  • Caleb: Mandarin, imagining going viral as the white guy who “stuns at the Chinese restaurant.”
  • Carly: Spanish, though admits she struggled to retain it in school.

4. Injury Conspiracies and Sudden Language Acquisition

[11:59–13:39]

• FedEx Accident Urban Legend: Carly floats the urban legend that if you get hit by a FedEx truck, you get a $2 million payout—information gleaned from a man at Rockaway Beach. Caleb is skeptical.
• Brain Trauma/Learning Languages: They joke about stories of concussion leading to spontaneous foreign language fluency and segue into beliefs about the supernatural.

5. Ghosts, Hauntings & Queer Spirituality

[13:39–16:56]

• The Lesbian Ghost Cohort: Carly earnestly shares that she believes her grandfather (Poppy) is haunting her Brooklyn apartment, based on a friend’s psychic senses.
• Caleb’s Skepticism: Caleb counters that flickering lights and depression are not evidence of ghosts and jokes about “batshit” lesbian friends.
• *Ghost Sex: The segment devolves into queer ghost erotica and the moral quandaries of spectral incest.
  • "What if the only way he can move on is if he fucks you? What if Poppy's a really good guy, but he can't leave Purgatory until he fucks his granddaughter?" – Caleb [14:54]

6. Losing Your Mind & Queer Psychosis

[17:57–18:44]

• Schizophrenia Fears: Both share the fear of losing their minds or having a psychotic break; Carly jokes that, if Caleb did, he could “snap out of it.”
  • "You'd look in the mirror and be like, we're done with this." – Carly [18:39]

7. Workplace Catastrophes and Restaurant Culture

[23:05–34:36]

• Job Disaster Swap: Carly confesses to eating leftover fries from plates and being fed by a busser who liked watching her eat (“unblinking”). Caleb calls a former boss live for character witness. Both recount restaurant jobs as breeding grounds for misbehavior and mayhem.
  • "I'd empty [fries] into my server thing, and go to the bathroom and eat them." – Carly [23:09]
  • "At Applebee's, my boss would play 'I'll Be' and barely not cry." – Caleb [33:07]
• Communal STIs: Carly details a chlamydia outbreak at her Italian restaurant job, where “every level of service had chlamydia.”

8. Restaurant Romance, Management, and Small Town Memories

[34:57–36:11]

• Queer Romance at Work: Carly asks Caleb about queer romance in restaurant life. He had none; “There were no gay people where I grew up.”
• Small Town Eats: Both reminisce on Applebee's and Outback as high cuisine in their hometowns, praising the power of half-off appetizers.

9. Smoking, Fashion, & Self-Presentation

[37:00–41:38]

• Smoking Aesthetics: They riff on the hot/cool look of smoking, despite both finding the reality kind of disgusting. Caleb has never smoked; Carly insists he’d “hold it wrong.”
  • "You'd use your back two fingers. Like Mr. Bean." – Carly [39:06]
• Fashion Inadequacies: Caleb reflects on not feeling “carefree” or cool in fashion, just “careless.” Carly echoes not caring about designers and both lament lack of time and style to look effortless.
• Designer Name Snobbery:
  • "Why is it spelled like that? And then they do the little croissant, and it's like: shut up." – Carly [41:38]

10. Standing Up for Yourself & Unhinged Hamptons Energy

[42:50–45:43]

• Petty Slights: Caleb recalls being condescended to about “haberdashery” as a teen; Carly almost goes off on a Hamptons shop lady for body-shaming her friend. Both admit to letting a lot of minor slights go but feeling near a breaking point.
  • "The more people call me nice, the more I want to prove them wrong." – Carly [45:49]

11. Pets, Cat Psychics, and Emotional Support Animals

[46:06–48:30]

• Carly’s Persian Cat: She describes her devotion to her flat-faced cat, Walter, and shares about a gift psychic reading revealing his "ADHD" and wish for a cape.
• Caleb’s Reluctance: Caleb is skeptical about both the cat psychic and Walter’s “menacing” looks but takes it in stride.

12. Seasonal Feelings: Overrated Summer, Queer Christian Autumn

[48:35–50:54]

• Why Summer Sucks: Carly claims “Summer’s really overrated” and details the misery of sweating through five pairs of underwear daily. Caleb declares autumn the perfect season, noting nostalgia, folk music, and Halloween’s queer resonance.

13. Weirdness, Astrology, and Rapidfire True/False

[51:18–54:42]

• How Strange Is Carly?: Caleb rates her a “public 4–5, private 7” and they compare astrological charts (Aquarius, Scorpio, Leo placements, and more).
• True/False Quiz: Carly plays a feverish round of trivia for $50, getting rapid-fire facts right and wrong.

Notable Quotes & Moments

• Caleb (on customer service):
  “Verizon is going to hell... They don’t care. Everything’s gotten so much worse.” [01:05]

• Carly (on ghosts):
  “Grandpa was wrestling in the space… Sometimes I step back there, I start to cry. My cat stares into it.” [13:27]

• Caleb (on restaurant pay):
  “I am alive today because, during multiple times when I was too broke to live, you gave me chicken wings for $3.” [35:53]

• Carly (on being called nice):
  “The more people call me nice, the more I want to prove them wrong.” [45:49]

• Caleb (on autumn):
  “It’s so clear to me that autumn is the most ideal season that we have, and people don’t respect it enough.” [49:36]

Highlighted Segments with Timestamps

• Customer Service Jobs & Stories: [00:55–04:35]
• Queer Friendship & Boundaries: [04:41–08:16]
• Tattoo & Swastika Story: [08:29–10:21]
• FedEx Truck Urban Legend & Ghost Discourse: [11:59–16:56]
• Restaurant Mayhem & STIs: [23:05–34:36]
• Applebee’s & Outback Memories: [35:21–36:11]
• Smoking & Fashion Confidence: [37:00–41:38]
• Being “Nice” & Repressed Rage: [42:50–45:49]
• Pets, Cat Psychic, and Emotional Labor: [46:06–48:30]
• Seasonal Feelings – The Case for Autumn: [48:35–50:49]
• True/False Quiz: [53:27–54:42]

Final Thoughts

The episode manages to be both loose and thematically cohesive as Caleb and Carly dig into the realities of queer friendship, boundaries, and the weird jobs that shaped them. Through rapid-fire banter, dark digressions, and heartfelt moments, listeners get a clear sense of their affection and comic synergy. The segment on ghosts and spirituality versus skepticism stands out, as does their mutual longing for autumn as a cure for queer malaise.

Find Carly on Instagram.
"So True" is available on Headgum and major podcast platforms.