08. I Don't Miss My Ex, I Miss My Admin Assistant with Ali Kolbert

08. I Don't Miss My Ex, I Miss My Admin Assistant with Ali Kolbert

Comedian, actor, and writer Ali Kolbert joins Emma for a long-overdue catch-up that goes deep on the brutal mechanics of dating, breakups, and queer identity. They open on the gaslighting breakup Ali's still recovering from — the ex who insisted "I'm gay, he's just my friend" and is now a year-plus into dating that man — and the universal agony of not trusting your own gut until it's too late. From there: what it's like being single-single for the first time in years, why being a messy partner makes you "a guy, but a shitty guy," whether every long-term couple is secretly up to something, and the art of breaking a rule inside an open relationship. They get into passing, masculine vs. feminine energy, "sneaky man ones," why neither of them can stand lesbian porn, and the strange new phenomenon of straight people being obsessed with gay people on stage. Plus two listener dilemmas: a cuddle-not-sex bar encounter that somehow ended in a marriage, and the person who realized their breakup felt less like heartbreak and more like losing the one assistant who knew the context of all their enemies. ✅ Stay Connected With Me: 👉 Instagram: https://www.instagram.com/emmawillmann [https://www.instagram.com/emmawillmann] 👉 TikTok: https://www.tiktok.com/@iamemmawillmann [https://www.tiktok.com/@iamemmawillmann] 👉 Twitter: https://twitter.com/iamemmawillmann [https://twitter.com/iamemmawillmann] #EmmaWillmann #AliKolbert #GAYDHD #QueerComedy #ComedyPodcast #LGBTQComedy #LesbianComedy #StandUpComedy #Breakups #QueerPodcast #FunnyPodcast

Why I Spent an Entire Wedding Befriending a Homophobe | BONUS EP

A solo deep-dive bonus episode where Emma gets back from a mini comedy tour and can't stop thinking about perception — what it feels like to walk on stage and feel a room "register" you in real time. That spirals into the legendary tale of the Texas wedding where she set out to win over the most conservative guy there (sleeveless cowboy tuxedo and all) and ended up more popular than the bride. Then comes the main event: a full investigative deep dive into Willa Ford, the early-2000s "bad girl" pop star behind "I Want to Be Bad," whose entire second-album rollout got buried when her single dropped on September 11th. Emma traces what actually happened to her (spoiler: interior design), connects it to her own show getting derailed by COVID and George Floyd, and lands somewhere unexpectedly philosophical about media, Marshall McLuhan, and the meaning we project onto the things we put into the world. Plus: who lives rent-free in your brain (Chingy? Trillville?), and an Am I the Asshole about a vegetarian husband, a steakhouse anniversary, and a wife who went to Outback alone to prove a point.

07. "How About an Over-the-Pants Handj*b?" — The Worst DM Ever with Caitlin Peluffo

Comedian, actress, star of Kevin Hart's Funny AF, and aspiring empire-builder Caitlin Peluffo joins Emma for an unhinged, very funny, very gay conversation about dating, desire, and the absolute state of modern courtship. They get into the frozen-peas-on-the-TV trick for sneaking past strict parents, getting caught by mom mid-hookup in high school, and Caitlin's quest to get back out there after seven months off the market. The two break down what actually makes a DM work (public account, good photo, don't be creepy — the bar is in hell), the worst messages they've ever received, and the guy who fumbled a sure thing in the most baffling way possible. Plus: why having a man plan the date is the ultimate green flag, flirting getting harder the longer you do comedy, body image and the shame that lingers, and Caitlin's new YouTube special Prosciutto Rose (and what that title actually means). Plus an Am I the Asshole about phone-location sharing in relationships.

06. Yawning, Quantum Physics & Curing Anger With Pettiness with Elle Orlando

omedian, actress, and podcaster Elle Orlando joins Emma for an episode that goes everywhere. They start with the anxiety symptom no one talks about — excessive yawning — and somehow end up explaining the double-slit experiment. Elle breaks down the four-day healing retreat led by her dad's girlfriend (a self-taught spiritual healer who studied with Tibetan monks), the finger muscle-testing technique that supposedly makes your body answer questions honestly, and her theory that every possible version of your life is happening in a parallel dimension right now. They also get into aging parents who quietly start depending on their kids, the ick of dating a guy with major Long Island "hey girl" energy, and how Elle cured her anger problem by replacing it with world-class pettiness. Plus: ADHD and Vyvanse shame, growing up dyslexic and getting shuffled into special ed, and an Am I the Asshole deep dive about a mom who hid her daughter's childhood ADHD diagnosis for over a decade.

05. Catfishing, Closet Cases & Code Switching with Akeem Woods

Comedian Akeem Woods joins Emma Willmann for a hilarious and surprisingly deep conversation about gay hookup culture, getting catfished, and what it really means to code switch as a queer person of color. Akeem opens up about growing up closeted in Florida, fabricating a fake girlfriend named Kiana on Facebook, and the moment he finally came out at 25. Emma shares her own unforgettable Craigslist catfish story involving a "supermodel" and a 7-Eleven in Queens — and yes, it ends exactly how you'd expect. They also dig into the heated rivalry around the show 'Rivals' (yes, they watched it), the manosphere documentary and whether those guys are just deeply closeted, bottom-shaming inside the gay community, and why straight women at gay bars is a whole conversation we still need to have. This episode gets real about the exhaustion of never fully belonging in any one space — whether you're the only Black person in a queer room or the only queer person at the family cookout. Plus: top, bottom, or versatile? The discourse is alive and well. Funny, honest, and genuinely moving in places — this one's a must-watch.