My Worst Date

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

November 12, 2025 100 mins
This week Keegan, Cassi and Christina discuss going out rules, improv sex lives and Halloween costume wins. The FMK is between Nick Kroll, Nick Offerman and Matthew Lillard.  Going into the bad dates, Keegan shares a date in a shed, Christina shares a role reversal date and Cassi shares a date with an extensive list of everything that's wrong. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Celeste Ma...
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This week Keegan, Cassi and Christina discuss if having a boyfriend is embarrassing and what the rules for hugging your friend's husband are. The FMK is between Scorpios Joaquin Phoenix, Gerard Butler and Penn Badgely. Going into the bad dates, Christina shares a date with a man fresh out of a breakup, Keegan shares a date swiping Tinder on the date, and Cassi shares a date seeking a sensual lover. Christina wraps it up in the tr...
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October 29, 2025 97 mins
This week Keegan, Cassi and Christina talk about Lily Allen's very detailed new album about David Harbour and why you shouldn't wrong a musician. The FMK is between red flag guys from the 80s, 90s and 00s. Going into the bad dates, Cassi shares a date that can't shake a bad gut feeling, Keegan shares an awful dinner date with surprise ingredients and Christina shares a date built up for 2 years that slowly deflates on an air matt...
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October 22, 2025 81 mins
This week Keegan, Cassi and Christina go through a wild Am I The Asshole question and play FMK with David Cross, Weird Al Yankovic and Paul Scheer. Going into the bad dates, Christina shares a Snapchat truth or dare, Keegan shares a date that goes from love bombing to absolute psycho and Cassi shares a date with kissing cousins. Christina wraps it up in the true crime segment, Tainted Love, with the story of Marie Spannhake. Lea...
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October 15, 2025 86 mins
This week Keegan, Cassi and Christina talk about the new Taylor Swift album and the dangers of being dickmatized. The FMK is between Keke Palmer, Megan Thee Stallion and Hayley Williams. Going into the bad dates, Keegan shares a disappearing movie date, Cassi shares a date that's mega racist and Christina shares a date with a wild open door policy. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Mauric...
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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. Learn more about your ad choices. Vis...
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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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. Learn more about your ...
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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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. L...
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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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. Learn more about your ad choices. Visit megaphone.fm/adchoices
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