Podcast Summary: "So True with Caleb Hearon" — Episode: "Maggie Winters Sees the Comments"
Date: November 20, 2025
Host: Caleb Hearon | Guest: Maggie Winters
Network: Headgum

Episode Overview

In this lively and heartfelt episode, comedian Caleb Hearon welcomes fellow comic and podcaster Maggie Winters for a wide-ranging, candid, and very funny conversation. The pair riff on everything from travel and eating habits as working comics, unsolicited advice and Internet comments, to family dynamics, creative ambitions, and what it means to find joy (plus frustrations) in everyday life and career. Both bring their signature mix of self-aware humor and unfiltered honesty, making for an engaging exploration of what’s "so true" in 2025.

Key Discussion Points & Insights

1. Names, Nicknames, and Generational Queerness

• Opening Banter: Caleb jokes about calling Maggie “Marguerite,” which was easier for her French host family to pronounce than “Maggie.”
  • “I just think it's fancy. I like it.” — Caleb [01:39]
• Older Women & Queerness: They discuss the coded queerness in older generations—how women’s close female friendships were often more significant than marriages.
  • “Her deepest, most important relationships with a woman in her life. ... That's a gay woman, honey.” — Caleb [03:17]

2. Chronic Skin Stuff, Chicago, and Brand Gifting

• Eczema Realness: Maggie’s had eczema since birth, leading to funny misidentification stories (“people think it’s ringworm”) [04:09].
• Chicago Nostalgia & Weber Grill: They reminisce about discovering the (in their youths) “super fancy” Weber Grill, only to later realize it’s a very dad-restaurant.
• Brand Gifting: Caleb jokes that as his podcast gets bigger, brands actually send him things just with a mention—sometimes it’s fun, but often it’s junk.
  • “Brands need to stop sending shit. Unless it is extremely cool.” — Caleb [05:36]
  • “Don’t send a hat—send chocolate.” — Maggie [06:01]

3. Travel, Food, and Self-Control on the Road

• The ‘Away Life’ Illusion: Both talk about “away life” vs. “real life”—how being on tour or traveling for work used to feel like a free pass for bad habits, until that lifestyle became the norm and the consequences real.
  • “I have realized my home life is fake and my away life is life.” — Caleb [06:57]
• Airport & Fast Food Rituals: The struggle to break “airport snack” rituals, putting themselves on timeouts (KFC, Flips pretzels).
  • “Every fat person has a thing they’ve had to put themselves on timeout for.” — Caleb [08:16]
  • Maggie’s KFC story, Amsterdam edition: getting high and thinking “there’s no greater food in the world.” [09:20]
• Unbothered by Gross News: Even stories about “dead mouse in a KFC bucket” don’t actually deter them.

4. Emotional/Mental Health, Affirmations, and Delusion (in a Good Way)

• Comic Vulnerability: Life on tour is exhausting; after a show, all they want is alone time—but that doesn’t always feel good either.
  • “I have to be the clown tonight... and then you open your phone and the internet’s like, 17,000 children died today and someone I hate is on vacation.” — Maggie [11:22]
• Audition FOMO: The brutal comedy/actor life—hopeful waiting on roles, only to discover Meryl Streep got it.
• Affirmations & Coping: Caleb discusses downloading an affirmations app, leaning into “delusion” as a necessary mindset.
  • “I’m trying to make my brain so strong that I can handle anything that ever happens to me.” — Caleb [12:51]
  • The AI affirmation that moved him: “I am in charge of how I feel, and today I am choosing happiness.” [13:18]
• Focus on Process, Not Outcome: Caleb describes a recent creative shift—obsession with process over results, fueled by working on his film “Trash Mountain.”

5. Hotel Life Advice

• Best place to stay? Four star hotels.
  • “Two and one are obviously… not even in the conversation… Threes… no amenities. ... Five stars, too old, not as nice as a four star.” — Caleb [16:01]
• Hotel desk and reservation issues, credits frozen for “unusual” (i.e., generous) charitable donations.
  • “I am unusual. I am unusually kind.” — Caleb [17:48]

6. Fatness, Microaggressions & Leaving People Alone

• Performing Fatness: Both recount being patronized for doing totally normal things (ordering a burger without a bun, being told “good for you”).
• Random Diagnoses: Stories about being accosted with unsolicited medical or wellness advice—“You must be taking ashwagandha!” [53:47]
• General Sentiment: “Leave me alone!” — The phrase becomes a through-line/meme [21:13, 53:31]

7. Internet Comments & Screen-Mediated Policing

• Internet Outrage Fatigue: Discussing the experience of people getting “policed” for jokes and authenticity on the Internet versus real-life friendship context.
  • “The disconnect we’re having is that I have actual friends in real life... you live your whole identity on the internet.” — Caleb [26:09]

8. Pop Culture, TV, and Regional Representation

• Fat Reality TV: Maggie is deeply into shows like “1000-lb Sisters,” praising their joy and authenticity.
  • “They’re just the funniest people in the world... they both [eventually] lost a lot of weight… Tammy came out as pansexual!” — Maggie [29:04]
• TV vs. Music: Maggie’s a TV person (TLC, reality); Caleb’s a music person.
• They bond over Lily Allen, Audrey Hobert, and laugh at a "Mandela Effect" moment about “Pitch Perfect” puppets [30:31].

9. Gender, Authentically ‘She/Her,’ and Pop Empowerment

• Maggie expresses a bit of "girl envy," wishing she was more “gender bendy,” but ultimately identifies as a “strong she/her.” [31:38]
• They riff on Meghan Trainor’s body-positivity anthems, the weird blowback for fat jokes vs. jokes about thin people.

10. Food, Fast Food, and Satisfying the Soul

• Burgers & Sauce Philosophy: Riffing on “smash burgers” vs. “Mondo burgers,” sauce ratios, and the unique euphoria of being asked if you want a side of fruit.
  • “If I can’t grab it like this... your sandwich is too big.” — Caleb [32:54]
  • “The kind of self-satisfaction I feel when I order a side of fruit...” — Caleb [49:32]
• Road Life Consequences: Both have tried to cut fast food to avoid heartburn and acid reflux.

11. Podcasting as Process, Challenges, and New Projects

• Maggie’s New Podcast: “Literally Life Changing with Maggie Winters” — on the joys and perils of making something new, fighting for attention online, and how showing up is often the hardest, but best, part.
  • “Getting to laugh with people … is amazing.” — Maggie [36:14]
• Podcast Format Musings: Caleb reflects on how “So True” has become more vital to his creativity than expected, how segments evolve, and how it’s “a living organism.” [36:42, 62:08]
  • “Podcasting is art.” — Caleb [62:18]

12. Hypotheticals: The $3M Creative Project

• Both riff on what they’d do with $3 million to spend only on a creative project.
  • Maggie: Movie based on moving back with her parents, dad obsessed with complaining about Trump.
  • Caleb: A conceptual, slightly sci-fi “five minutes in the future” script he’s outlined.
  • Both: A yearning for an indie film revival — “Where are the Little Miss Sunshines?” [48:55]

13. "So True" to Maggie: Just Leave People Alone

• Maggie’s "so true": “Leave me alone... unless it’s with kindness.” [53:17]
• Real life examples: Uber drivers pushing supplements, people (unnecessarily) diagnosing her with ADHD.

Memorable Quotes & Moments

• On creative delusion:

  • “I’m genuinely trying to tap more into delusion. I moved away from it briefly... and now I’m trying to move back.” — Caleb [13:02]

• On Internet disconnect:

  • “You’re living a screen-mediated life... the only thing that gives you connection is policing and comments.” — Caleb [26:34]

• On body microaggressions:

  • “People think that fat people can’t do anything.” — Maggie [19:14]

• On unsolicited advice:

  • “You have to be taking ashwagandha.” — My Uber driver. I was like, no, I don’t!” — Maggie [53:47]

• On creative priorities:

  • “I want to make cool, weird, artsy indie films.” — Caleb [48:06]

• On process over outcome:

  • “I am actually genuinely focused on process at the moment. And I love it.” — Caleb [14:29]

• On the joy of ordering fruit:

  • “The kind of self satisfaction I feel when I order a side of fruit...” — Caleb [49:32]

Notable Timestamps

• Names, Generational Queerness: [01:35–03:40]
• Brand Gifting & Chocolate Rant: [05:13–06:10]
• Travel Diet Epiphany: [06:22–07:27]
• KFC & Fast Food Timeouts: [08:16–09:59]
• Affirmations & Mental Health: [12:28–13:59]
• Hotel Rankings & Travel Woes: [15:46–18:14]
• Internet Policing & Friendship: [25:24–26:56]
• New Podcast Process Talk: [35:32–36:42]
• $3 Million Creative Project: [42:05–47:14]
• Indie Movie Manifesto: [48:05–49:07]
• So True Segment/Leave Me Alone: [53:17–54:24]
• Fun with Famous People’s Emails & Group Texts: [55:17–57:26]

Episode Tone

Conversational, rambly in a charming and relatable way, full of honesty and playful self-deprecation. Both comedians balance sharp wit and quiet vulnerability, switching seamlessly from banter to sincerity. The spirit is collaborative, supportive, a bit anti-glam—genuinely friendship-forward and creatively encouraging.

For New Listeners

This episode is a great entry-point to So True. It’s packed with quotable moments, honest answers, and useful insight for anyone who travels, creates, or simply wants to feel less alone in trying to do “life” with humor and realism. Maggie’s right: sometimes what’s so true is simply the wish to be left alone—unless it’s for real-life laughter, connection, and a good sauce-to-veggie-to-meat ratio.

Listen to Maggie’s new podcast: Literally Life Changing with Maggie Winters
Check out Caleb’s work, upcoming film, and future projects on the podcast and on Substack.