My Worst Date
Ever been on a crazy bad date? You're not alone! Join hosts and best friends Keegan Winfield, Christina Conner, and Cassi Young-Paxton as they dish about pop culture, relationships, true crime and share stories from listeners and their past of the worst dating disasters.
Episodes
October 8, 2025 • 85 mins
This week Keegan, Cassi and Christina talk about AI companions and love scams. The FMK is between Keith Urban, Tom Cruise and Lenny Kravitz. Going into the bad dates, Cassi shares a date with a troubled married dude, Christina shares a hungover date and Keegan shares a date that can do impressions...maybe. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Evie Watson.
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October 6, 2025 • 24 mins
In this bite-sized episode Keegan, Cassi and Christina talk about the Burning Man Orgy Tent and jump into bad dates featuring model portfolios, surprise Porky Pigs, cosigning loans, soiled jeans, red pills at Olive Garden, unicorns, car troubles and secret wives.
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October 1, 2025 • 88 mins
This week Keegan, Cassi and Christina talk going out etiquette and cringe culture. The FMK is between Rivers Cuomo, Alanis Morissette and Nick Hexum.
Going into the bad dates, Christina shares a guy with the longest breakup text ever, Cassi shares a terrible repeat date and Keegan shares a guy's smelly turn off. Christina wraps it up in the true crime segment Tainted Love with the story of Seemona Sumasar.
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September 24, 2025 • 93 mins
This week Keegan, Cassi and Christina update about the Irish matchmaking festivals and talk aliens and the rapture. The FMK is between Libras Bruce Springsteen, Brie Larson and Glen Powell.
Going into the bad dates, Keegan shares a gold digging date at Applebee's, Cassi shares a high school date getting one-upped by a friend and Christina shares a date with interesting condom techniques. Keegan wraps it up in the true crime segmen...
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September 17, 2025 • 100 mins
This week Keegan, Cassi & Christina talk sex toys and body modification. The FMK is between short kings Marc Maron, Mark Ruffalo and James McAvoy.Going into the bad dates Cassi shares a date that just won't or can't stop talking, Kegan shares a date with surprise kids and Christina shares a date with a very memorable entrance. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Charlene Childers.Interested ...
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September 10, 2025 • 77 mins
This week Keegan, Cassi and Christina talk about hygiene drama on TikTok and Ireland's matchmaking festival. The FMK is between Pierce Brosnan, Paul Mescal and Cillian Murphy.
Going into the bad dates, Christina shares an awkward teenage date to the movies, Cassi shares a date throwing up into a fender bender and Keegan shares a date with surprise roommate. Christina wraps it up in the true crime segment, Tainted Love, with the s...
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September 3, 2025 • 91 mins
This week Keegan, Cassi and Christina discuss a reddit thread about a sister being uninvited to family functions due to husband's kink and play fmk with a foot fetish, exhibitionism and BDSM. Going into the bad dates, Keegan shares a date that left early to get back to an ex, Christina shares a chaos goblin on a road trip to Florida and Cassi shares a date from an actual horror movie. Keegan wraps it up in the true crime segment, T...
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September 1, 2025 • 34 mins
In this bite-sized episode Keegan, Cassi and Christina talk about the Burning Man Orgy Tent and jump into bad dates featuring model portfolios, surprise Porky Pigs, cosigning loans, soiled jeans, red pills at Olive Garden, unicorns, car troubles and secret wives.
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August 27, 2025 • 105 mins
This week Keegan, Cassi and Christina talk about how to rate yourself using the Spice Girl method and ASHBY on TikTok. The FMK is for Virgo season: Alexander Skarsgard, Pink and Colin Firth.
Going into the bad dates, Cassi shares a date that tries to sneak in backup, Keegan shares a date that brings family, and Christina shares a date that discovers Long Island Iced Teas. Cassi wraps it up in the true crime segment, Tainted Love, ...
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August 20, 2025 • 109 mins
This week Keegan, Cassi and Christina discuss homesteading and the low birth rate. The FMK is between Supermen Christopher Reeve, David Corensweat and Henry Cavill.
Going into the bad dates, Christina shares a date that heads out early, Cassi shares a college date that ends with a bang, and Keegan shares a date with an Andrew Tate fan. Christina wraps it up in the true crime segment, Tainted Love, with the story of Ruth Finley.
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August 13, 2025 • 77 mins
This week Keegan, Cassi and Christina discuss summer depression and Kendra falling in love with her psychiatrist. The FMK is between Jason Ritter, Dave Franco and Liam Neeson.
Going into the bad dates, Keegan shares a date that turns into a stalker, Cassi shares a date with a huge surprise and Christina shares a date that should really check their texts before sending. Keegan wraps it up in the true crime segment, Tainted Love, w...
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August 6, 2025 • 76 mins
This week Keegan, Cassi and Christina discuss moms and weight, microaggressions and ozempic. The FMK is between Selena Gomez, Salma Hayek and Michael Pena.
Going into the bad dates, there's date that keeps showing up uninvited, a disappearing party, surprise naked beaches, dudes crying and bowling.
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July 30, 2025 • 66 mins
This week Keegan, Cassi and Christina discuss making crow friends and vacations. The FMK is between dream vacations Fiji, Scotland and Egypt.
Going into the bad dates, there's a mom who set up a criminal date for her son, another naked surprise, a date too intoxicated, a date that wants a "real man", a dude trying to get his date to babysit and some poop in the road.
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July 23, 2025 • 56 mins
This week Keegan, Cassi and Christina talk about safety with men and porn and play FMK with Barack Obama, Maya Rudolph and Sebastian Stan. Going into the bad dates, there's a date that won't take no, someone bringing their wife to their date's job, labeling a date Do Not Answer, a date that admits to kidnapping, undercooked Korean BBQ and a freaking ventriloquist.
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July 16, 2025 • 65 mins
This week Keegan, Cassi and Christina talk low stakes drama and second hand embarrassment. The FMK is between summer drinks white wine, lemon shandy and moscow mule.
Going into the bad dates, there's one at a grocery store deli, a date showing off to friends, a date in dodgy London, divorce at a restaurant, prayer for dogs and an intoxicated therapist.
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July 9, 2025 • 55 mins
This week Keegan, Cassi and Christina discuss a reddit trophy wife post with the worst insult of all time. The FMK is between Risk, Clue and Trivial Pursuit. Going into the bad dates, there's the coldest date of all time, a strip club, a date too soon after a breakup, a date trying to pass off takeout as home cooking, a date used as a pawn, and a homemade sensory deprivation tank.
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July 7, 2025 • 32 mins
In this bite-sized bonus episode, Keegan, Cassi and Christina talk cat problems and dystopian thoughts, and laugh about dates with dying grandmas, Hades, Dance Dance Revolution, iguanas and ESPN.
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July 2, 2025 • 52 mins
This week Keegan, Cassi and Christina discuss r/badwomensanatomy and old Cosmo magazines. The FMK is between Solange, Post Malone and Pam Anderson.
Going into the bad dates, there's a date that wants to speed run a relationship, bad date bingo, first trip proposals, moles getting cheeky, more farts and for a twist, the best date of all time.
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June 25, 2025 • 72 mins
This week Keegan, Cassi and Christina discuss difficulties in setting boundaries as people pleasers and play FMK with Hermoine Granger, Maleficent and Nancy from The Craft.
Going into the bad dates, there are older married guys getting farting on, ordering extra food to go, washing off hamburgers, sex in public bathrooms, meeting the parents and surprise fiances.
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June 18, 2025 • 68 mins
This week Keegan, Cassi and Christina shout out fantastic listener write ins, and talk about No Kings protests and Tyler's amazing cruise karaoke. The FMK is between cruise lines Carnival, Royal Caribbean and Disney.
Going into the bad dates, Cassi shares a very special private guitar performance, Christina shares a rude date that chooses baseball over the Bachelor and Keegan shares a date that has no boundaries.
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