My Worst Date

My Worst Date Podcast LLC
  • 0.0 (0)
  • RELATIONSHIPS
  • UPDATED WEEKLY

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.

  1. 5 DAYS AGO

    Breadwinners and Breadlosers

    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

    1h 43m

  2. 28 JAN

    Weirds and Icks

    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 megaphone.fm/adchoices

    1h 17m

  3. 21 JAN

    A Cannon Event

    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 choices. Visit megaphone.fm/adchoices

    1h 46m

  4. 14 JAN

    Surviving...

    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

    1h 23m

  5. 7 JAN

    Don't Talk No Sh*t

    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

    1h 27m

  6. 31/12/2025

    Movie Review - When Harry Met Sally

    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

    42 min

  7. 24/12/2025

    Loser Behavior

    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 megaphone.fm/adchoices

    1h 37m

  8. 17/12/2025

    Everything Sucks

    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, Tainted Love, with the story of Blazej Kot. 15% off at https://uncommongoods.com/worstdate Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 25m
See All (482)

About

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.

Information

  • Creator
    My Worst Date Podcast LLC
  • Years Active
    2018 - 2026
  • Episodes
    482
  • Rating
    Explicit
  • Copyright
    © My Worst Date Podcast LLC
  • Show Website
    My Worst Date

You Might Also Like