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Comedian, actor, and producer James Tom joins Emma for a funny, deep, and genuinely moving conversation about spending 17 years in the wrong pool before finding his way home. James traces the whole arc: 13 years in the Girl Scouts, coming out at 14 and going all in, women's college, starting testosterone right before the pandemic on a hunch about his future career, and the Fire Island trip that quietly rearranged his entire sense of himself. They get into the spiritual difference between a butch lesbian and a twink, the crossed wires of being attracted to (and attractive to) people who were picking up on something you couldn't see yet, why transition is less an event than just getting older, reward-based brains and candy at funerals, and how a relationship can become a way to avoid sitting with yourself. Plus a shared love of porn talk, true crime, and reading Am I the A*****e first thing in the morning to feel normal.

Comedian and Funny AF finalist Winston Hodges joins Emma for a warm, funny, wide-ranging conversation about the strange truth that every good thing that happens to him seems to raise the stakes instead of lowering them. After ten years and a self-imposed deadline, Winston had made peace with not "making it" and was on a lake vacation when a casting email landed that turned out to be Kevin Hart's Funny AF — and his anxiety hasn't returned to baseline since.They get into the ten-day whirlwind of making the show, closing on a house, and getting a Cellar audition all at once, why success can feel more terrifying than failure, and Emma's uncanny (and hilarious) sixth sense for reading a room. Plus small-town life, the slow drift from young Republican to progressive, Winston's years teaching kids with autism, chain restaurants as a love language, and grief doing strange things to the body.

Comedian and classically trained actress Natalie Cuomo joins Emma for a very funny hang that eventually gets to her obsessive Hello Kitty claw-machine phase — the one that's left her apartment buried in stuffed animals and looking like a child lives there. Before that, they get into the specific humiliations of auditioning, including the self-tape that got Natalie's team to ask, in writing, whether she'd ever taken an acting class (she went to acting school), and the blonde-bombshell soap opera audition where they had to lower the camera for her.Emma gets into the acting feedback she keeps getting ("disingenuous," and yes, "autistic") for nodding the way she actually nods in real life, why "just be yourself" has never once worked, how Twitch became Natalie's one positive online space, and Emma's comment filter that blocks the words "women," "Ellen," and "not funny."

Emergency solo recording, because I had too much to report and no intention of letting my brain flit it into the ether. Last time I was high on my supply of mantras — turns out "I'm not someone who scrolls" lasted about seven days, and I'm ready to admit I'd medal at the Scrolling Olympics. Then a head cold, a Kansas City real estate gig, and a full health-anxiety spiral led to me buying a Life Alert bracelet at 40. And finally, the payoff I'd been saving: the sphincter specialist, the exam, the diagnosis, and the $6 Amazon fiber pills that may have quietly fixed everything. Plus whether I was, in fact, flirting with the sphincter doctor.

Comedian and science nerd Sarah Adelman joins Emma to talk sperm banks, big dick energy, anxiety, gossip, the placebo effect, and all the bizarre ways our brains shape reality. Sarah shares what it was actually like working at a sperm bank, why she thinks she found scientific evidence for “big dick energy,” and how seeing that much sperm changes a person. They also get into why gossip helps us bond, why embarrassing memories stick with us, whether being cringe is actually the key to getting good at something, and why Emma uses the placebo effect to convince herself a bad stand-up set is going great. Plus: failed cheating schemes, accidental doula meet-and-greets, emotional incest, space travel, butthole fingerprints, and much more.

Sex therapist Shavon Gaddy joins Emma for a very funny, very frank conversation that starts exactly where you'd expect — Emma's newly diagnosed weak inner sphincter and the fiber-supplement redemption arc that came with it — and somehow gets genuinely useful from there. They break down the actual difference between anxiety and depression, and between "being depressed" and a depressive disorder, plus why they don't hand out major diagnoses to 12-year-olds. They also get into the Madonna/whore issue in a long-term relationship (you can be a sweet pea AND a whore), the real difference between a kink and a fetish, why you should never yuck someone's yum, and a deep and committed exploration of the piggyback fetish.

Comedian Alex Kumin joins Emma for a conversation that goes 0 to 100 in the best way — funny, tender, and ultimately inspiring. Alex tells the story of finally meeting her longtime therapist in person, sobbing in her arms, and then falling into a three-week breakdown that turned out to be exactly the release she needed — decades of pushed-down feelings finally moving through her. (Content heads-up: they discuss surviving childhood sexual trauma, cancer, and survival in general.) They also get into the difference between CBT and DBT and holding two opposing truths at once, the fantasy of a "flatlined" middle-of-the-road existence vs. real equanimity, crying as release rather than something to medicate away, and learning to sit with feelings and say "I'm safe" now in a way you couldn't at 6, 21, or 35.

Elle Orlando is back — and this time she and I are doing a book club. Two dyslexic comedians who hadn't cracked a book in years both tore through Lena Dunham's memoir, and they get into everything it stirred up: feeling compassion for their 24-year-old selves, the wild Klonopin doses in the book, and how getting off Klonopin made Emma feel like she hadn't known herself in years. They also dig into where the "school system got my ass," being alternative thinkers displaced from the Midwest, being lifelong people-pleasers (and why this book felt like exposure therapy), the terror of asking for what you need before you've "made it," and learning guitar as healthy dopamine. Plus the mortifying gift of a mom who relates a little too personally to everything. Plus the usual Am I the A*****e to close it out.

Solo one this week. I get into the week that gave me a little breakdown, the mantra that pulled me out of it, my favorite neuroscientist who identifies as a dolphin, and why I spike my matcha with Celsius.

Comedian Onika McLean joins for a hilarious conversation that opens with a full-blown rant about trying to "ground" in a New York City park that's been overrun by transplants and their so-called emotional support animals. Onika breaks down the real service these dogs provide, the rescue dogs dragging their new Minnesota owners around Bed-Stuy, and why she's been reduced to standing in a basin of Epsom salt at home just to relax. From there, we get into everything we try because TikTok told us to, chasing morning sunlight while fighting the urge to grab our phones, nervous systems and stomach issues, and the theory that a forehead kiss is just someone trying to steal your brain power.

Comedian Oscar Aydin joins for an unhinged, very gay, very funny conversation between two friends with zero filter — capped off by a gay-slang lightning round where they rank each other with words like slay, shade, chosen family, and butch queen. Along the way: Emma announcing she got "rear-ended" and Oscar needing to know which kind, the fantasy always beating the reality (see: dressing up for the cable technician), and the amateur porn couple Emma followed so long she felt genuinely happy when they moved into a nicer house. They also get into the comedy of porn comment sections, reclaiming the word "queer" and Emma's mom's total confusion about it, and whether Larry David would survive as a gay man.

Comedian and actress Brittany Schmitt joins Emma for a raw, funny conversation that starts with the eerie feeling that your phone knows your love life better than you do. Mid-breakup, Brittany's feed filled up with reels describing her exact situation — and she breaks down the meme that finally got her off the wrong train. They get into self-righteous anger as a drug, the interior designers who stole $25K, why saying "I'll never" paints a target on your back, and rerouting your brain the way athletes do.

Comedian Eva Evans joins for a sharp, funny conversation about saying the wrong thing online and the people waiting to punish you for it. Eva breaks down what happened when a follower told her a word she'd grown up hearing as a compliment in Jamaica was actually rooted in an ethnic slur — and how posting the apology publicly, hoping to help other people learn, turned into the thing she regrets most. They get into the self-righteousness of "how did you not know that," the impossibility of code-switching without getting dragged for it (see: calling a Jamaican TRN a "social security number"), why outrage outperforms everything else in the algorithm, and how to protect your peace when the comments never stop. Plus: Eva's three-year process writing a joke about dating a trans guy that would actually land, leaving Christianity, getting into crystals, stress that shows up in your body, Jamaican beauty standards vs. American self-doubt, and the Bob Marley mix-up that turned Emma bright red on stage. Plus an Am I the A*****e about a friend who sold a concert ticket after the buyer wouldn't pay up.

Comedian, actress, and TED talker Jaye McBride joins Emma for a funny and surprisingly tender conversation about growing up trans before there was even a word for it. Jaye opens with the childhood moment of seeing a trans person on TV — that flash of "that's me" — followed by her father's worst-possible reaction. They get into coming out as trans in 2007, how Pride has changed over two decades, the theory that the most rigidly conservative people are hiding the most, losing religion, neurodivergence, celebrity crushes, and the racism baked into how the NFL treated Black quarterbacks.

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 s****y 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👉 TikTok: https://www.tiktok.com/@iamemmawillmann👉 Twitter: https://twitter.com/iamemmawillmann #EmmaWillmann #AliKolbert #GAYDHD #QueerComedy #ComedyPodcast #LGBTQComedy #LesbianComedy #StandUpComedy #Breakups #QueerPodcast #FunnyPodcast