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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

111:02

A Shared Experience

My Worst Date ·

2026/04/15

This week Keegan, Cassi and Christina talk about the unwarranted backlash against Aubrey Plaza as well as the new Netflix doc on Lamar Odom. The FMK is between Willie Nelson, Will Arnett and William Shakespeare. Going into the bad dates, Keegan shares a date pressuring drinks and more, Christina shares a date that didn't realize it was a date and Cassi shares a date that turns into love-bombing. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Barry Winchell. Learn

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58:26

Boots on the Ground

My Worst Date ·

2026/04/08

This week Keegan, Cassi and Christina talk about Kristi Noem's husband, Keegan's cat attack and a listener correction about Peyton Manning. The FMK is between Michael Jordan, Meg Ryan and Nicholas Cage. Going into the bad dates, Keegan shares a date ruined by back acne, Christina shares a date ruined by cocaine and Cassi shares a date that pretends not to know what sex is. Book link for guy's wife:

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28:35

Shorty - 85

My Worst Date ·

2026/04/06

Join Keegan, Cassi and Christina for a bite-sized episode talking about Summer House drama, religious trauma dates, muppet kisses, running from the cops and crashing small parties. Learn more about your ad choices. Visit megaphone.fm/adchoices

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98:15

Catching Print

My Worst Date ·

2026/04/01

This week Keegan, Cassi and Christina discuss birthday shenanigans and the most unbelievable cake of all time. The FMK is between Freddie Mercury, Elton John and Peyton Manning.Going into the bad dates, Christina shares a date coming to terms with her advancing age, Cassi shares a wingwoman horror story and Keegan's shares a wild date at Walmart. Christina wraps it up in the true crime segment, Tainted Love, with the story of Ira Bernstein. Learn more about your ad choices. Visit

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74:58

Hollyweird

My Worst Date ·

2026/03/25

This week Keegan, Cassi and Christina talk weird opinions on ballet and opera and breakdown for this week's FMK of Judy Garland, Carrie Fisher and Billy Ray Cyrus.Going into the bad dates, Keegan shares a date that has to pretend to be family, Cassi shares a date that gets too smashed for The Notebook and Christina shares a date with a nerd night fail. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Sade Robinson. Learn more about your ad choices. Visit

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97:12

Gallows Humor

My Worst Date ·

2026/03/18

This week Keegan, Cassi and Christina discuss rich wishes and play FMK with Nathan Fillion, Alan Tudyk and Kyle McLaughlin.Going into the bad dates, Cassi shares a date with one disaster after another, Christina shares a catfish date that tries to score and Keegan shares a date with no clue why their surprise is terrifying. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sharon Kinne. Learn more about your ad choices. Visit megaphone.fm/adchoices

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95:10

A Whole Timmy Chalamet

My Worst Date ·

2026/03/11

This week Keegan, Cassi and Christina talk about AI relationships and the state of dating apps. The FMK is between Timothy Chalamet, Katy Perry and Chelsea Handler.Going into the bad dates, Christina shares a date that spends the rest of their life trying to escape, Keegan shares a date with a conspiracy theorist and Cassi shares a date at a puppet festival. Christina wraps it up in the true crime segment, Tainted Love, with the story of Rob Metzer. Learn more about your ad choices. Visit

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77:51

Good For Jazz

My Worst Date ·

2026/03/04

This week Keegan, Cassi and Christina talk Alpine Divorce and conspiracy theories. The FMK is between Jennifer Garner, Steve Buscemi and Yoko Ono. Going into the bad dates, Cassi shares a date that just hangs out all day, Keegan shares a terrifying newspaper date and Christina shares a rollercoaster date with wine and coke. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sophia Dorothea of Celle. Learn more about your ad choices. Visit megaphone.fm/adchoices

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35:30

Shorty - 84

My Worst Date ·

2026/03/02

Join us in a bite-sized episode featuring healthcare and drugs, foot lickers, zits, egg lovers and beta testing apps for the zombie apocalypse. Learn more about your ad choices. Visit megaphone.fm/adchoices

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83:21

Anything Goes

My Worst Date ·

2026/02/25

This week Keegan, Cassi and Christina discuss the ANTM documentary, Reality Check, as well as other reality show terrible moments. The FMK this week is between Tom Selleck, Christopher Walken and Madonna.Going into the bad dates, Keegan shares a bad date that returns with a weapon, Cassi shares a date that shows up with surprise kids and Christina shares a date too stoned for When Harry Met Sally. Keegan wraps it up in the true crime segment, Tainted Love, with the story of the Kotze

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92:14

Find Local Bad Bunnies In Your Area

My Worst Date ·

2026/02/18

This week Keegan, Cassi and Christina discuss the cheating Olympian and the Epstein files. The FMK is between New Girl Guys Nick, Winston and Schmidt.Going into the bad dates, Christina shares a wild date with dinner, the gym and shrooms, Cassi shares a date with a unique proposition, and Keegan shares a date with too many red flags at their grown age. Christina wraps it up in the true crime segment, Tainted Love, with the story of Norma McCauley. Learn more about your ad choices. Visit

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82:50

Waka Waka

My Worst Date ·

2026/02/11

This week Keegan, Cassi and Christina talk about some absolutely bananas My Strange Addictions as well as early 00s reality shows. The FMK is between Cyndi Lauper, Cameron Diaz and Melissa McCarthy.Going into the bad dates, Cassi shares a gross and disappointing hookup, Keegan shares a nightmare bachelor pad and Christina shares a dangerous date with a highschooler. Cassi wraps it up in the true crime segment, Tainted Love, with the story of the Tagged Killer. Learn more about your ad choices

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103:01

Breadwinners and Breadlosers

My Worst Date ·

2026/02/04

This week Keegan, Cassi and Christina discuss personal assistants and how awful AI is. The FMK is between James Earl Jones, Billie Eilish and Robert Pattinson.Going into the bad dates, Keegan shares a date that won't kiss but wants head, Christina shares a listener's first grown up breakup, and Cassi shares the worst hookup ever. Keegan wraps it up in the true crime segment Tainted Love with the story of Hannah Pettey.Learn more about your ad choices. Visit megaphone.fm/adchoices

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77:07

Weirds and Icks

My Worst Date ·

2026/01/28

This week Keegan, Cassi and Christina unlock a new ick and discuss the Are We Dead app. The FMK is between Idris Elba, Macauley Culkin and Wayne Gretsky.Going into the bad dates, Christina shares a date with a drunk short king, Keegan shares a date with a sob story and Cassi shares a date claiming to have superpowers from another dimension. Christina wraps it up in the true crime segment, Tainted Love, with the story of Maria Munoz. Learn more about your ad choices. Visit

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106:01

A Cannon Event

My Worst Date ·

2026/01/21

This week Keegan, Cassi and Christina confront negative inner voices and beg for one stop shop full makeovers. The FMK is between Jimmy Buffet, Channing Tatum and Justin Timberlake. Going into the bad dates, Cassi shares a date with a delusional entrepreneur, Keegan shares a fishing date with a naked guy and Christina shares a bad date remembered and retold 15 years later. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Dee Ann Warner. Learn more about your ad

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83:18

Surviving...

My Worst Date ·

2026/01/14

This week Keegan, Cassi and Christina talk about getting over being sick, the hard start to 2026, going commando and perimenopause. Going into the bad dates, Keegan shares a date that goes off on his mother, Christina shares a date pulling out needles and Cassi shares a date that needs to keep their eyes on the road. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Geoffrey Hood & Molly LaRue. Learn more about your ad choices. Visit megaphone.fm/adchoices

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87:22

Don't Talk No Sh*t

My Worst Date ·

2026/01/07

This week Keegan and Christina talk about the holiday break and resolutions. The FMK is between Capricorns Kate McKinnon, Zoey Deschanel and Nina Dobrev.Going into the bad dates, Christina shares a lying, pretentious date that gets put out by smoking and Keegan shares a wild ride with spiders, meth and screaming. Christina wraps it up in the true crime segment, Tainted Love, with the story of Todd Garton. Learn more about your ad choices. Visit megaphone.fm/adchoices

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42:21

Movie Review - When Harry Met Sally

My Worst Date ·

2025/12/31

Closing out 2025 with a perfect movie - join Keegan, Cassi and Christina for a watch of When Harry Met Sally and from everyone at My Worst Date, have a happy new year!Learn more about your ad choices. Visit megaphone.fm/adchoices

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97:11

Loser Behavior

My Worst Date ·

2025/12/24

This week Keegan, Cassi and Christina talk about theater kid cringe moments and play FMK with favorite Rob Reiner movies. Going into the bad dates, Cassi shares the drama from a restaurant's holiday party, Christina shares a date that shows all the red flags in relation to her friend's husband and Keegan shares a date getting third-wheeled by a dog. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sarah Hartsfield. Learn more about your ad choices. Visit

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84:47

Everything Sucks

My Worst Date ·

2025/12/17

This week Keegan, Cassi and Christina discuss surviving the holidays and how terrible shopping has become. The FMK is between holiday songs O, Holy Night, Charlie Brown Christmas and All I Want For Christmas Is You. Going into the bad dates, Keegan shares a date that peed the bed, Cassi shares a story of a boss bringing his girlfriend (not his wife) to the holiday party and Christina shares a girl who turned it all the way up at her office party. Keegan wraps it up in the true crime segment,

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