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PODCAST

My Worst Date

My Worst Date Podcast LLC

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.

society & culture relationships

All Episodes

100:49

We Contain Multitudes

My Worst Date ·

2025/09/17

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 in the toy we were talking about - got 10% discount at LELO here for

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77:23

Stinky Elmo

My Worst Date ·

2025/09/10

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 story of Mark Jensen. Learn more about your ad choices. Visit

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91:56

Special Feet

My Worst Date ·

2025/09/03

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, Tainted Love, with the story of Robert Spangler.Learn more about your

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34:37

Shorty - 81

My Worst Date ·

2025/09/01

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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105:49

Not All Kevins

My Worst Date ·

2025/08/27

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, with the story of Lana Turner. Learn more about your ad choices

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109:19

In The Car?

My Worst Date ·

2025/08/20

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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77:58

Hot Hands

My Worst Date ·

2025/08/13

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, with the story of Kristine Healy. Learn more about your ad choices

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76:41

Black & White Cookie

My Worst Date ·

2025/08/06

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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66:00

Blame TLC

My Worst Date ·

2025/07/30

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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59:04

Oral History

My Worst Date ·

2025/07/23

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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68:28

No Class

My Worst Date ·

2025/07/16

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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58:07

Fancy Panties

My Worst Date ·

2025/07/09

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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34:18

Shorty - 80

My Worst Date ·

2025/07/07

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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55:54

Attitude is Everything

My Worst Date ·

2025/07/02

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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75:42

Pennies

My Worst Date ·

2025/06/25

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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71:46

Hard Mike

My Worst Date ·

2025/06/18

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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57:07

Lucky Lass

My Worst Date ·

2025/06/11

This week Keegan, Cassi and Christina talk about a date on a budget and the farce of the male loneliness epidemic. The FMK is between Himesh Patel, Jeffrey Wright and Bobby Cannavale. Going into the bad dates, there's a surprise date to a science museum, blue cheese breath, crashing another date, lies about age and a duster date having a bad Tuesday. Learn more about your ad choices. Visit megaphone.fm/adchoices

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56:08

Who Is This Diva?

My Worst Date ·

2025/06/04

This week Keegan, Cassi and Christina get real about perimenopause and menopause, play FMK with Jean Smart, Helen Mirren and Katey Sagal, and share terrible date stories featuring petty breakups, mouthy divas, Myspace, ethical dilemmas and meeting the parents. Learn more about your ad choices. Visit megaphone.fm/adchoices

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34:12

Shorty - 79

My Worst Date ·

2025/06/01

This bite-sized bonus features bad Bachelor dates and TikTok Grandma drama, and bad date stories with pocket knives, stolen tips and Yaris shootouts. Learn more about your ad choices. Visit megaphone.fm/adchoices

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56:39

Word Up

My Worst Date ·

2025/05/28

This week Keegan, Cassi and Christina discuss both sides of a breakup, play FMK with Geminis Mackelmore, Richard Madden and Michael Cera, and share bad date stories featuring games, parties, first date shits and baby pics.Learn more about your ad choices. Visit megaphone.fm/adchoices

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480 results

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