Lovett or Leave It – "Sedition: Impossible"
Date: November 22, 2025
Host: Jon Lovett
Guests: Timothy Simons, Pat Regan, Hayley Kiyoko
Location: Dynasty Typewriter, Los Angeles
Episode Overview
In this lively, Thanksgiving-themed episode of Lovett or Leave It, Jon Lovett brings together actor Timothy Simons, comedian Pat Regan, and singer/author Hayley Kiyoko for a night of comedy, political breakdowns, and heartfelt pre-holiday vibes. Mixing national headlines—with Trump’s waning grip on the GOP, political absurdities, and the Epstein files saga—with candid discussions on queerness, family, romance, and gratitude, Lovett orchestrates a fast-paced, supportive, and irreverent live show that both skewers the week’s news and celebrates community.
Key Discussion Points & Insights
1. The State of the Trump Presidency
- Trump’s Declining GOP Power: Lovett recaps Trump’s losing battle in Congress, public feuds with Marjorie Taylor Greene, and inability to whip votes his way.
- Quote: “Trump finally became a lame duck president.” (03:35)
- Marjorie Taylor Greene Fallout: Trump lashes out at Greene, threatening to back her primary challenger and publishing online tirades with personal attacks.
- Lovett: “Trump turning on his allies. Shocking, said Mike Pence, reenacting January 6th with Karen in a length of rope…” (07:00)
- Congressional Dissent: More House Republicans buck Trump over the Epstein Files Transparency Act.
- Epstein Files Released: With Congress nearly unanimous, DOJ commits to releasing Epstein-related files—Lovett and guests joke about the symbolic catharsis and pervasive corruption.
- Trump’s Foreign Policy Escalations: Trump threatens war with Venezuela and the fictional "Cartel de los Solas," drawing parallels to previous political scapegoating.
- Lovett: “It’s not that far from Trump declaring war on a case of the Mondays.” (10:09)
- Trump and Authoritarians: Discussion of Trump’s continued coziness with foreign autocrats, notably Saudi Crown Prince MBS and handling of Khashoggi’s murder.
- Lovett: “The problem isn’t that it’s embarrassing to bring it up. The problem is that you aren’t embarrassed all the other times.” (11:50)
2. Political Satire & Calls for Civic Responsibility
- Democratic Response Video: A group of Democratic lawmakers post a video reminding military members to obey only lawful orders, drawing Trump’s ire and his calls for punishment by death.
- Lovett: “It’s the kind of video you wish you didn’t have to make, like a hostage video or an apology for having your wedding at a plantation.” (12:11)
- Trump’s Nuclear Posturing: The dread of Trump's repeated authoritarian threats is met with both gallows humor and serious reminders of democracy’s resilience.
- Lovett’s Rebuke: Urges listeners not to understate democracy’s endurance against authoritarian impulses.
- Lovett: “Authoritarianism always looks stronger than it is, and democracy always looks weaker than it is…” (55:03)
3. Turkey of Truth – Comedy Friendsgiving
[18:25 – 33:38]
Lovett, Simons, Kiyoko, and Regan field banter and comedic Thanksgiving “truths” and awkward dinner-table questions from the “Turkey of Truth”—diving into personal anecdotes, self-aware quips, and relatable discomforts:
- Timothy’s Faux Hawk:
- Simons: “[I asked my stylist for] an elevated methamphetamine [look].” (20:20)
- Responds to fame’s weird hair-related aftershocks with deadpan absurdity.
- Pat’s “Normal Gay Haircut” Ritual:
- Regan: “I say, I want a normal gay haircut. Make me look like the most normal gay person you can imagine. Works like a charm, don't you think?” (21:52)
- Hayley’s Music Release Pressures:
- Kiyoko: “As an artist, you do one thing, and then the first thing someone asks is, when are you going to do more?...Yeah, soon. Maybe next year.” (22:16)
- Family Consuming Your Work:
- Regan: “I'm, like, so scared they would consume it...If anyone I’m related to listens to this, I will set myself on fire.” (23:07)
- Sauce Discourse & Political Parallels:
- Comedic debate over condiments, Trump’s filet-o-fish fixation, and the “shame” of sauce preferences.
- Lovett: “Ketchup is…It has…It's just like…It's a wall of flavor. Basically, ketchup makes every food kind of like dessert.” (26:04)
- Being Typecast:
- Simons: “The shit that I get asked to audition for is essentially a photocopy of the things that I have done before. And all the stuff I get offered is the stuff that is the exact opposite…” (27:55)
- Sapphic Romance and Representation:
- Kiyoko: Explains her new book, “Where There’s Room for Us,” inspired by her own relationship and providing more diverse queer love stories — where "no lesbians die."
- Kiyoko: “If you allow yourself to dream, you can be who you want to be.” (30:55)
- Simons, joking: “Eventually all lesbians will die. Like everybody dies.” (31:16)
- Born This Way Debate:
- Lovett and Kiyoko discuss moving beyond "couldn’t help it" narratives in LGBTQ+ acceptance, especially for women.
- Lovett: “I like that we’re past the 'couldn’t help it' family.” (32:53)
4. Audience Q&A: Holiday Romance (“Surely Somebody Wants This”)
[35:21 – 44:53]
Audience members and guests swap advice on relationships, family holidays, and love:
- Going to the Partner’s Family – Proving Your Worth:
- Kiyoko: “You do not need to prove your worth ever.” (37:45)
- Romantic Fails:
- Simons: “I accidentally told my college girlfriend’s little brother that Santa Claus wasn’t real…” (38:56)
- Holiday Breakup Dilemma:
- Regan: “I was once dumped on Amazon Prime Day. It’s like, don’t dump someone on a day that’s gonna happen every year and that they’re gonna get emails about. The body will remember.” (40:57)
- Consensus: Break up before the holidays, don’t make memories or guilt-compound.
- Engagements & Rings:
- Kiyoko: “I proposed to her this year and then she’s going to propose to me…and I really didn’t think this through.” (42:36)
- ‘Considerate’ vs ‘Romantic’ Partner Roles:
- Prompted by a New Yorker article on throuples; group concludes that it’s healthy to recognize relationship dynamics, with Pat and Hayley trading mutual affirmations.
5. Gratitude Wheel
[46:38 – 53:04]
Panelists share non-ironic gratitude, ranging from personal relationships and fans to good barbers, movie theaters, and resiliency.
- Pat: Grateful for a great haircut and his barber Minia—“Now identify as her being a mother figure to me.” (48:06)
- Hayley: “I’m grateful for my fiancée, my fans, and the rain. We needed rain.” (49:46)
- Timothy: For his kids, resilience, and the resurgence of communal moviegoing:
- “I like that there has been…a return to that [going to movie theaters] in a conscious way.” (51:57)
- Lovett: For the enduring power of democracy:
- “Authoritarianism always looks stronger than it is, and democracy always looks weaker than it is…We are not easily ruled and will not be.” (55:03)
Notable Quotes & Memorable Moments
- “Republican members of Congress are 100% kids that ate the marshmallow.” (Lovett, 04:45)
- “You meet a charming guy…You have the exact same taste in art, which is no art…” (Lovett lampooning Trump/Greene, 06:58)
- “It’s a vague reference to no actual group…like the Itty Bitty Titty Committee.” (Lovett, 10:20)
- “Much like Elphaba refused to go along with the illegal orders of the Wizard, added Jeff Goldblum. The Wicked promo campaign is out of control.” (Lovett, 12:52)
- “I asked the person who cuts my hair…I was like, can you…give me, like, an elevated methamphetamine?...someone wrote a thing about it in GQ.” (Simons, 20:17)
- “If anyone I’m related to listens to [my podcast], I will set myself on fire.” (Regan, 23:07)
- “If you allow yourself to dream, you can be who you want to be.” (Hayley Kiyoko, 30:55)
- “But eventually all lesbians will die…like everybody dies…” (Simons, 31:16—deadpan humor)
- “I was dumped on Amazon Prime Day. And it’s like, don’t dump someone on a day that’s going to happen every year…” (Regan, 41:10)
- “I think we are more powerful than they are…” (Lovett, 55:24)
Important Segment Timestamps
- Political Recap / Trump & GOP Drama: 02:00 – 13:00
- Comedy Friendsgiving / Turkey of Truth: 18:25 – 33:38
- Audience Holiday Romance Q&A: 35:21 – 44:53
- Gratitude Wheel: 46:38 – 53:04
- Lovett's Final Reflections on Democracy: 53:04 – 56:35
Tone and Language
The episode maintains Lovett’s signature blend of acerbic political satire, rapid-fire jokes, and self-deprecating candor. The banter between guests is irreverent and campy, with poignant moments of authenticity, especially in the discussions of LGBTQ+ narratives, family pressures, and gratitude. Pat Regan provides dry observational comedy, Hayley Kiyoko brings warmth and sincerity, and Timothy Simons’s deadpan delivery punctuates the conversation throughout.
Summary for the Uninitiated
This episode sums up the week’s political chaos with biting humor and sees Lovett and his panel shifting effortlessly between national news absurdities, personal confessions, and holiday advice. If you’re seeking cathartic political comedy, relatable family/romantic dilemmas, and queer representation—with sharp wit but a generous holiday spirit—this Lovett or Leave It is your Friendsgiving essential.