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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

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

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

en-us

82:40

God Forbid She Has a Hobby

My Worst Date ·

2025/05/21

This week Keegan, Cassi and Christina talk about TikTok scams and a disappearing husband. The FMK is between Yellowstone, Zion and Sequoia National Parks.Going into the bad date stories, there's surprise spiders, bad jerk off jokes, Troll dolls, stealing stranger's food and experimental jazz. Learn more about your ad choices. Visit megaphone.fm/adchoices

en-us

54:33

Get Your Affairs In Order

My Worst Date ·

2025/05/14

This week Keegan, Cassi and Christina discuss 100 Americans vs 100 brits and this year's Met Gala looks. The FMK is between Teyana Taylor, Janelle Monae, and Brian Tyree Henry. Going into the bad dates, Christina shares an observed bad date at a restaurant, Keegan shares a bad date in a tough bathroom situation and Cassi shares a date with way too much going on to be dating. Learn more about your ad choices. Visit megaphone.fm/adchoices

en-us

94:11

If I'm Here, I'm Already There

My Worst Date ·

2025/05/07

This week Keegan, Cassi and Christina discuss porn and 100 men versus 1 gorilla. The FMK is between Pools, Lake and Ocean. Going into the bad dates, Cassi shares a date that ruined a blanket fort, Christina shares a date that had to make sure everything was evenly split and Keegan shares a date with a surprise in his pants. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Catherine Martinez.Learn more about your ad choices. Visit megaphone.fm/adchoices

en-us

36:59

Shorty - 78

My Worst Date ·

2025/05/05

In this bite-sized episode, Keegan, Cassi and Christina discuss faking your death to get out of a hard conversation, laugh about dinosaur conspiracies, and mistaken communication. Learn more about your ad choices. Visit megaphone.fm/adchoices

en-us

107:44

Strange Nut

My Worst Date ·

2025/04/30

This week Keegan, Cassi and Christina talk about My Strange Addiction, hygiene and baby awards. The FMK is between Fergie, Mariah Carey and Katy Perry. Going into the bad dates, Keegan shares a relationship where the lie has gone way too far, Cassi shares a date that goes from a play to a peep show and Christina shares a date with mistaken supplements. Keegan wraps it up in the true crime segment, Tainted Love, with the story of the Columbo Family murders. Learn more about your ad choices. Visit

en-us

104:09

Grow Up, Peter

My Worst Date ·

2025/04/23

This week Keegan, Cassi and Christina talk about constant flatulence and baby men. The FMK is between Robert Pattinson, Michelle Pfeiffer, and Jamie Dornan.Going into the bad dates, Christina shares a date with a selfish lover, Cassi shares a relationship ruined by the Satanic Church and Keegan shares a warning about giving that Nice Guy a chance. Christina wraps it up in the true crime segment, Tainted Love, with the story of Craig Titus and Kelly Ryan. Learn more about your ad choices. Visit

en-us

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