Long Winded with Gabby Windey

Episode: Glen Powell and Charlie Kirk
Host: Gabby Windey
Release Date: September 25, 2025

Episode Overview

In this episode, Gabby returns after a brief break—explaining her much-needed time off and setting expectations for her podcast-going forward. She dives into trademark territory: frank, relatable discussions on mental health, astrology, pop culture, and current events. The episode flows from light-hearted self deprecation and scholarly musings (about hair and astrology) to thoughtful and comedic critique of media culture, before landing squarely on an unfiltered, nuanced response to the assassination of Charlie Kirk. Gabby does what she does best: breaking down serious topics with wit, vulnerability, and a sharp dose of humor.

Key Discussion Points and Insights

1. Gabby’s Life Update, Mental Health, and Hotel Living

[01:08 - 11:30]

• Taking a Break: Gabby discusses taking a week off the podcast, proudly owning her boundaries and adjusting expectations. She shares the transparency behind scheduling "breaks" in her contract.
• New York Recap: Detailing her almost hermit-like stay at The Bowery hotel—going out only for American Spirits, cold medicine, or to return a used Amazon podcast light at Staples.
• On Hotel Conveniences: “Why would I step outside when I have railroad styled window panes that open so the fresh air can come to me?”
• Student Loans Joke: “One ballpoint pen and a green highlighter is not going to save you from your student loans. So better enjoy now because there’s only hell to come. I’m just kidding, I’m just kidding.” (06:50)
• Health Tangent: Touches on her health anxieties, use of zinc nose spray ("Cannot recommend enough"), and how colds always feel like a major crisis.

2. Astrology, Hair Theories, and Identity

[11:30 - 15:19]

• Makes playful connections between astrological signs and hair types (“All the Virgos had bobs”), while maintaining a tongue-in-cheek skepticism about astrology’s power.
• White Witch Theory: “Apparently if you have your period on an eclipse, it means you’re a White Witch. Whenever I have a chance to tell you about my period, I’m going to take it.” (13:40)
• Describes “period legs” and openly jokes about her body’s functions to foster relatability.
• On mental health and medication: “I’m on a slew of antidepressants…Lamictal is the best thing that’s ever happened to me. It’s really been my drug of choice.”

3. Pop Culture Shit Talk: Glenn Powell, Travis Kelce, and Men in Media

[16:10 - 27:41]

• Men Infiltrating Editorial Spaces: Gabby humorously laments the rise of men on magazine covers, referencing Travis Kelce’s GQ shoot as “an assault on my vision”.
• Mustard-Yellow Birkin Rant: “Did he have to play that little Hermès game to get to the Birkin he wanted?…They bait you with a Birkin and then they switch to an Hermès scarf. Nothing wrong with the scarf, but I came here for the Birkin.” (19:44)
• Glenn Powell GQ Feature: Gabby unexpectedly compliments Glenn Powell for embracing a hyper-masculine, campy cover:
  • “It was giving lesbian. It was giving trans man. It was giving Love Lies Bleeding.” (21:40)
  • “Now I’m a fan. Before, I probably didn’t like him for no reason, might I add. For absolutely no reason. But here I am, a fan. He’s got a fan in me.”
• State of American Men: Sarcastically questions why men are only now figuring out their identities: “You guys have had literally 2,000 years to figure it out. Women know. We’ve been knowing.” (25:05)

4. The Charlie Kirk Assassination: Caution, Conspiracy, and Media Critique

[27:41 - 63:30]

Gabby’s Approach

• Delayed Response: Explains taking a week to process before speaking on the Charlie Kirk assassination, to avoid misinformation and allow the facts to settle.

Gabby’s Personal Take & Government Cynicism

• On being ‘watched’: Jokes about the CIA or “an agent” listening to her podcast and getting added to a government list for criticizing the president:
  • “If I’m not on the list, I do take it personally because... Who’s not listening to Long Winded? This should be ubiquitous, the title on everybody’s tongue.” (29:50)
• Mocked Political Allegiance:
  • “I’m fully red pilled. I’m not even being funny. I’m not even kidding. This isn’t even a joke. I’m borderline scarlet fevered.” (31:00)
  • “Take my credit card, roll back my rights. I don’t care.” (sarcastically, mocking political fatalism)

Analysis of the Killing

• On the Video: “It’s terrifying. Honestly, after seeing the video, I got just this overall sense of doomdom, because this is what our country has become. We are literally seeing someone die in the most cryptic possible way right before our eyes on social media.” (36:36)
• Conspiracy & Media Criticism:
  • Suggests there is “something bigger” than just one radicalized individual at play—emphasizes the symbolic nature (“cryptic symbolism”) of Kirk’s assassination and questions if the whole event is being used as a scare tactic to chill free speech.
  • “It felt like these days nothing is as it seems. Like if it walks like a duck and quacks like a duck and looks like a duck, it’s probably a duck call. This is where we’re at, living in this society under this government Occam’s razor. Not around here you don’t.” (37:22)
• Disapproval, Not Celebration: Makes it clear she doesn’t agree with Kirk’s ideology, but doesn’t celebrate his death: “I do not agree with his ideology and either. I mean, for obvious reasons... but the gruesome symbolic way in which he died is really scary.” (39:10)

Religion, Gun Rights, and Ironic Death

• Critiques Kirk’s outspoken pro-gun rights stance:
  • “He was shot literally as he was speaking about gun rights, which I don’t think it was ironic. I think it was in spite of. I think it was very on purpose.” (41:23)
  • Points out the disconnect between religious rhetoric about “God-given rights” and the modern reality of guns: “God didn’t know what the fuck a gun was back then. He couldn’t have. I don’t know when artillery was invented, but it’s like he was still wearing a toga. They didn’t even have, like, inseams yet.” (40:50)

Free Speech; Fear and Humor

• Reflects on the growing threats to free speech and describes the assassination as “death by free speech,” satirically ranking it alongside “death by AI” as American fears.
• Memorable quote: “So which is it going to be first? Death by First Amendment or death by AI? Which is going to take us first?” (49:12)
• Even as she critiques, Gabby’s tone is skeptical yet never cruel—she advocates for free expression, even for those she vehemently disagrees with.

Media Theatrics, “Evidence,” and Distrust

• Bullet Engravings & Governor Cox: Mocks the media spectacle around allegedly engraved bullets ("you're gay lmao") as reported by Governor Cox, calls for actual evidence rather than just official statements (“Where’s your hair? But all we’ve seen is Governor Cox reporting...”). (54:45)
• On Conspiracies & Distractions:
  • Satirically suggests the narrative and evidence shifting is “fan fiction from the FBI.”
  • “It all smells fishy. It smells fishy like the Pacific Ocean. I’m not talking about the Atlantic Ocean, which is much cleaner. The Pacific Ocean that’s ridden with sewage.” (58:07)

On Dangerous Rhetoric, Platforms, and Youth

• Critiques the inherently one-directional nature of campus speaking tours and how young, impressionable students are easy targets for unchallenged ideology:
  • “There wasn’t much room for discussion or nuance when an 18-year-old... is watching you pose a question and then the other person just kind of like stonewalls you and just repeats the same stuff over and over.”
• Self-Deprecation about Evolving Beliefs: “Look at how far I’ve come from when I was 18 to 22 to now. I believed in heterosexuality back then. My frontal lobe was still growing.” (50:30)

Notable Quotes & Memorable Moments

• Astrology and Hair:
  • “I have a theory that astrological signs carry the same characteristic among the same signs regarding your hair… I’m a Leo moon and Leos are said to have good hair. Look at this. As I’ve said before, it’s the one good thing my mother gave me.” (07:13)
• On Conspiracy:
  • “My brains lie in the string of my G.” (28:27, joking about being put on a government list)
• Mental Health Vulnerability:
  • “Lamictal is the best thing that’s ever happened to me. It’s really helped with the depression. It’s really helped with that pit in my stomach.” (13:15)
• Pop Culture Riffing:
  • “It was giving lesbian. It was giving Trans man. It was giving Love Lies Bleeding. Have you guys seen that movie?” (21:40)
• On Kirk’s Death:
  • “We are literally seeing someone die in the most cryptic possible way right before our eyes on social media. I mean…the video was traumatizing. It was so sick. And for us to have access to that, it’s like really scary.” (36:45)
• Government Skepticism:
  • “Gov. Cox with his bald head that literally somehow has less hair than my pussy lips, even after laser hair removal. Let me tell you, they are similar surface areas. Where’s your hair?” (56:35)
• Whip-Smart Ending:
  • “This is where I leave you. So until next time, I’m long winded.” (63:10)

Key Timestamps

• [01:08] Gabby’s life update, break explanation, The Bowery hotel, health routines
• [06:50] Staples, back-to-school culture, student loans joke
• [11:30] Astrology, Leo hair, Virgo bobs, White witch period theory
• [13:15] Medication, Lamictal, mental health reflection
• [16:10] Editorial space, Travis Kelce’s GQ shoot—rant on men in media
• [19:44] Birkin bag tangent
• [21:40] Glenn Powell GQ feature, gender/queer admiration
• [25:05] Sarcastic commentary on “the state of American men”
• [27:41] Introduction to Charlie Kirk discussion
• [29:50] CIA/government watch humor
• [36:36] Reaction to Charlie Kirk video, conspiracy thinking, Occam’s razor joke
• [40:50] Gun rights, religious rhetoric, “God didn’t know what the fuck a gun was…”
• [49:12] Free speech and fear (“Death by First Amendment or death by AI?”)
• [54:45] Critique of “evidence,” media reporting, Governor Cox
• [58:07] “Fan fiction from the FBI” and mockery of media narratives
• [63:10] Closing thoughts

Overall Tone and Style

Gabby's signature blend of confessional humor, cultural critique, and unvarnished honesty keeps the show sharp. There’s a clear sense of irreverence—she makes fun of sacred cows on both sides, from wellness trends to pop culture to politics. Her monologue walks the line between thoughtful skepticism and comedic absurdity; existential dread is always cut with a winking self-awareness.

In Summary

• Gabby returns to deliver personal updates, astrology hot takes, and trenchant pop culture criticism, before deep-diving into the public assassination of Charlie Kirk and what it portends about American society, media, free speech, and the state of public trust.
• She artfully balances humor, skepticism, and empathy—making complex events accessible for listeners.
• The episode is a ride: moving from zinc up the nose and hair horoscopes, to the dangers of manufactured media, ending with a reminder that the search for truth is "fishy, like the Pacific Ocean."

“This is where I leave you. So until next time, I’m long winded.” (63:10)