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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

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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82:46

F*ck, Marry, Second Husband

My Worst Date ·

2025/12/10

Check out today's sponsor, Beducated: https://beducate.me/worstdate code worstdate for 60% off!This week Keegan, Cassi and Christina discuss how awful it is when your partner's family is your biggest bully, pranks and superstitions. The FMK is between Nicholas Hoult, Bill Pullman and Jon Stewart. Going into the bad dates, Christina shares a depressing date bowling, Keegan shares a back on the dating scene list of assholes and Cassi shares some work party drama. Christina wraps it up in the true

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32:46

Shorty - 83

My Worst Date ·

2025/12/08

We're back! In this bite size episode, Keegan, Cassi and Christina talk holiday party potlucks, drama and shenanigans and laugh about clueless dates, finger foods, the Heimlich maneuver and spaghetti noodles. Learn more about your ad choices. Visit megaphone.fm/adchoices

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39:09

Holiday Movie Review: Hot Frosty

My Worst Date ·

2025/12/03

You asked for it and we delivered. In this bonus tainted love movie episode from our Patreon feed, we cover the Christmas sensation, Hot Frosty! Happy Holidays, Worsties!We will return with a brand new episode next week, and appreciate your understanding as we navigate a rollercoaster of a year - we love you so much! Learn more about your ad choices. Visit megaphone.fm/adchoices

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70:45

Too Stupid to Live ft. Keegan & Christina

My Worst Date ·

2025/11/26

My Worst Date… in SPACE!! This week Keegan and Christina join the show Too Stupid to Live to answer the MOST IMPORTANT question of all time: What happens when a super chill and easygoing person gets ABDUCTED BY ALIENS?! Today the show reviews Renegade Love ($2.99) by Ann Aguirre. Book: Renegade Love by Ann Aguirre Amazon Paperback To find Becky and Too Stupid to Live: Apple Podcasts Spotify YouTube Substack TikTok Instagram Due to recent events, we've had to

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100:07

Getting Stuffed

My Worst Date ·

2025/11/19

This week Keegan, Cassi and Christina discuss a date not offering food and beige flags. The FMK is between Stuffing, Mashed Potatoes and Gravy and Macaroni & Cheese.Going into the bad dates, Cassi shares a date full of sex facts, Keegan shares an AOL catfish and Christina shares a rollercoaster date at a Peddler's Mall. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Simeonette Mapes-Crupi. Learn more about your ad choices. Visit megaphone.fm/adchoices

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100:10

Challenge Accepted

My Worst Date ·

2025/11/12

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 Manno. Thanks to our sponsor, Beducated. Go to

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82:46

I'll Load Your Dishwasher

My Worst Date ·

2025/11/05

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 true crime segment, Tainted Love, with the story of Sarah Maria

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97:56

You're Not The Boss of Me

My Worst Date ·

2025/10/29

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 mattress. Cassi wraps it up in the true crime segment, Tainted Love, with

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81:04

Can Get It

My Worst Date ·

2025/10/22

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

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485 results

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