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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

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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86:32

Arrest Me, Daddy

My Worst Date ·

2025/10/15

This week Keegan, Cassi and Christina talk about the new Taylor Swift album and the dangers of being dickmatized. The FMK is between Keke Palmer, Megan Thee Stallion and Hayley Williams. Going into the bad dates, Keegan shares a disappearing movie date, Cassi shares a date that's mega racist and Christina shares a date with a wild open door policy. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Maurice and Maralyn Bailey.Learn more about your ad choices. Visit

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85:43

Guess That Voice

My Worst Date ·

2025/10/08

This week Keegan, Cassi and Christina talk about AI companions and love scams. The FMK is between Keith Urban, Tom Cruise and Lenny Kravitz. Going into the bad dates, Cassi shares a date with a troubled married dude, Christina shares a hungover date and Keegan shares a date that can do impressions...maybe. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Evie Watson.Learn more about your ad choices. Visit megaphone.fm/adchoices

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24:29

Shorty - 82

My Worst Date ·

2025/10/06

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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88:55

Thumbs Up & Block

My Worst Date ·

2025/10/01

This week Keegan, Cassi and Christina talk going out etiquette and cringe culture. The FMK is between Rivers Cuomo, Alanis Morissette and Nick Hexum. Going into the bad dates, Christina shares a guy with the longest breakup text ever, Cassi shares a terrible repeat date and Keegan shares a guy's smelly turn off. Christina wraps it up in the true crime segment Tainted Love with the story of Seemona Sumasar. Learn more about your ad choices. Visit megaphone.fm/adchoices

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93:37

Marked Safe from Ugly Boys

My Worst Date ·

2025/09/24

This week Keegan, Cassi and Christina update about the Irish matchmaking festivals and talk aliens and the rapture. The FMK is between Libras Bruce Springsteen, Brie Larson and Glen Powell.Going into the bad dates, Keegan shares a gold digging date at Applebee's, Cassi shares a high school date getting one-upped by a friend and Christina shares a date with interesting condom techniques. Keegan wraps it up in the true crime segment Tainted Love with the story of Joanne Witt. Learn more about your

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480 results

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