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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

87:34

Never Romanticize A Man

My Worst Date ·

2025/01/29

This week Keegan, Cassi and Christina talk about social media and getting scammed out of almost a million dollars by fake Brad Pitt. The FMK is between Elizabeth Banks, Paris Hilton and Joseph Gordon Levitt.Going into the bad dates, Christina shares a date going hard on a Tuesday night, Cassi shares a date with only blue foods and Keegan shares a disappointing high school reunion with a crush. Christina wraps it up in the true crime segment, Tainted Love, with the story of Joy Silverman. Share your

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89:00

Where's The Beef?

My Worst Date ·

2025/01/22

This week Keegan, Cassi and Christina discuss TikTok, Red Note, Neil Gaiman and how 2025 has jumped the shark. The FMK this week is between popular resolutions saving money, working out and drinking water.Going into the bad dates, Cassi shares a date passed out naked in a car, Keegan shares a date that thinks he's cheating, and Christina shares a date that floods a bathroom and then raps about it. Cassi wraps it up in the true crime segment, Tainted Love, with the story of LaNell Barstock. Learn

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90:56

Mediocre Jab Job

My Worst Date ·

2025/01/15

This week Keegan, Cassi and Christina talk about the LA fires and play FMK with movies Hook, Beetlejuice and Erin Brockovich.Going into the bad date stories, Keegan shares a date with two exes commiserating loudly, Christina shares a date with a major Disney adult and Cassi shares a date that has to mission impossible out of the house. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Carly Ryan. Share your bad date stories with us at

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118:14

Dumbo Ears

My Worst Date ·

2025/01/08

This week Keegan, Cassi and Christina talk new year feelings and body changes. The FMK is between romance tropes forced proximity, Beast & Beauty and fake relationship.Going into the bad dates, Christina shares a date that can yodel, Keegan shares a drunken comedy show date, and Cassi shares a date with terrible jokes. Christina wraps it up in the true crime segment, Tainted Love, with the story of Moriah "Mo" Wilson. Got a bad date story to share? Go to https://myworstdatepodcast.com and follow us

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34:47

Shorty - 74

My Worst Date ·

2025/01/06

In this bite-sized episode, Keegan, Cassi and Christina discuss a wild second date update, a bad date with Gollum, rotisserie chicken and holiday party messiness. Learn more about your ad choices. Visit megaphone.fm/adchoices

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87:55

Friend of the Pod, Lexapro

My Worst Date ·

2025/01/01

Happy new year, Worsties! This week Keegan, Cassi and Christina make 2025 predictions and play FMK with Denzel Washington, Lin Manuel Miranda and Pitbull. Going into the bad dates, Cassi shares a date a fake NYE party, Keegan shares a rude date in basketball shorts and Christina shares a date with a list of bad qualities. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Truus and Freddie Oversteegen. Got a bad date to share? Go to https://myworstdatepodcast.com! Learn

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102:38

Holiday Feed Swap - Boobies & Noobies feat. My Worst...

My Worst Date ·

2024/12/25

Hi Worsties! Taking a breather for the holiday season, but not to worry - still have a great episode for you! From our podcast bestie Boobies & Noobies & author of Santa Monica Baby, Kelly Reynolds, we give you our episode from 2019 reviewing the spicy novel, Stocking Stuffers by Erin McClellan. Follow Kelly on Instagram @authorkellyrey and subscribe to Boobies & Noobies! Learn more about your ad choices. Visit megaphone.fm/adchoices

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86:19

Crunchy Towels

My Worst Date ·

2024/12/18

This week Keegan, Cassi and Christina discuss AI and astrology along with the embarrassing stories on TikTok trending. The FMK is between Garrone Noone, Julian Sewell and Drew Afualo.Going into the bad dates, Keegan shares a hungover date that gets an allergic reaction, Cassi shares a hungover guy trying to get to the airport and Christina shares a wild family holiday gift story. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Jeffrey MacDonald. Go to

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86:58

Notions

My Worst Date ·

2024/12/11

This week Keegan, Cassi and Christina talk about Barry Keoghan & Sabrina Carpenter and play FMK with the New Girl loft, the Practical Magic house and the cottage from The Holiday.Going into the bad dates, Christina shares a date who is super into astrology, Keegan shares a date whose family is super into religion and Cassi shares a date whose plus one got turnt at a company holiday party. Christina wraps it up in the true crime segment, Tainted Love, with the story of Peggy Hopkins Joyce. Learn

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101:18

Hollow Shells

My Worst Date ·

2024/12/04

This week Keegan, Cassi and Christina discuss a rough situation where a woman finds out her husband thinks she's unattractive and play FMK with Hollow Chocolate Santa, Candy Canes and Fruitcake.Going into the bad dates, Cassi shares a date that's really a hang with friends, Keegan shares a date that printed out questions and Christina shares a date on the Captain's boat. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Lucretia Borgia. Got a bad date story to share? Go

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33:01

Shorty - 73

My Worst Date ·

2024/12/02

Join Keegan, Cassi and Christina for bite-sized bad date stories featuring closure sex with exes, Zoolander and titty calendars and calling for Mum at the worst time - this one's a wild ride, guys! Got a bad date story to share? Go to https://myworstdatepodcast.com or follow us on Instagram, TikTok and YouTube @myworstdatepodcast. Learn more about your ad choices. Visit megaphone.fm/adchoices

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76:35

The W Column

My Worst Date ·

2024/11/27

This week Keegan, Cassi and Christina discuss the "women in male fields" trend and play FMK with Theo James, Lucy Liu and Don Cheadle.Going into the bad dates, Keegan shares a date that borrowed food from the restaurant he works at, Christina shares a date with a ruined fantasy and Cassi shares a date that loves the movie Tarzan. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Aqua Tofana. Share your bad date story at https://myworstdatepodcast.com! Learn more about

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85:03

Turning This Spaceship Around

My Worst Date ·

2024/11/20

This week Keegan, Cassi and Christina talk about aliens and the best way to break up with a cheater. The FMK is between Martha Stewart, Viola Davis and Jennifer Aniston. Going into the bad dates, Christina shares speed dating fails, Cassi shares a date at the Cheesecake Factory that hates everything, and Keegan shares a drunken date in Vegas. Christina wraps it up in the true crime segment, Tainted Love, with the story of Jeanne de Clisson. Got a bad date story to share - go to

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67:25

What Can You Do

My Worst Date ·

2024/11/13

So, this is not a typical episode...the past week has been a tough roller coaster and all of us have struggled with our feelings on the outcome of the election - what it means for ourselves, what it means for dating, and what we can do to prepare for the next four years.We'll be back with regular content next week but we hope if you'd like to listen that you can gain some helpful tips or just feel like you're commiserating with your girlfriends. We're making it available to all of you, our

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88:26

Snake Charmers

My Worst Date ·

2024/11/06

This week Keegan, Christina and Cassi talk about audio porn and Hot Frosty and play FMK with Scorpios Frank Ocean, Eric Dane and Jimmy Kimmel. Going into bad date stories, Cassi shares a date singing for their life in the restroom, Christina shares a date that loves cats, and Keegan shares a scary date that won't get out. Cassi wraps it up in the true crime segment, Tainted Love with the story of Milliard Aldridge. Support us and our sponsors! To get 15% off your next gift, go to

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36:35

Shorty - 72

My Worst Date ·

2024/11/04

Join Keegan, Cassi and Christina for bite-sized bad date stories featuring bad oral hygiene, bad manners and wild first date baby talk. Share your bad date story at https://myworstdatepodcast.com! Learn more about your ad choices. Visit megaphone.fm/adchoices

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103:58

Life Is Short

My Worst Date ·

2024/10/30

This week Keegan, Cassi and Christina discuss what happens when the sister in law goes after the widower and play FMK with horror leading men Penn Badgely, Anthony Hopkins and Bill Skaarsgard.Going into the bad date stories, Keegan shares a date with a total jerk, Cassi shares a date too drunk and stoned and Christina shares a date with a demonologist. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Tammy Williams. Anyone with information on Williams’ whereabouts is

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97:37

S.P.D.

My Worst Date ·

2024/10/23

This week Keegan, Cassi and Christina talk about the Pluto transit and dating plus-sized. The FMK is between Andrew Garfield, Ed Sheeran and Milo Ventigmilia. Going into the bad dates, Christina shares a date with BO, Cassi shares a date with a know it all full of red flags and Keegan shares a date that moves in and wreaks havoc. Christina wraps it up in the true crime segment, Tainted Love, with the story of Nada Altentawi. Learn more about your ad choices. Visit megaphone.fm/adchoices

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103:50

There Were Signs

My Worst Date ·

2024/10/16

This week Keegan, Cassi and Christina discuss Mom advice on dating and deliver a PSA for hot peppers. The FMK is between the Loveland Frog, the Jersey Devil and Chupacabra.Going into the bad dates, Cassi shares a date that ghosted for queso, Christina shares a Warhammer reference gone wrong and Keegan shares a date that drank way too much. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Dianne Kidder Keidel. If you have a story to share, reach out to us at

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105:52

Different Strokes

My Worst Date ·

2024/10/09

This week Keegan, Cassi and Christina talk about the body in the rug and Secret Lives of Mormon Wives. The FMK is for Libra season: Julie Andrews, Susan Sarandon and Dakota Johnson. Going into the bad date stories, Keegan shares a date with a mystery, Cassi shares a date with nothing going for them and Christina shares a date afraid of what's in the dark. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Ed & Lorraine Warren. Please help hurricane victims:

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480 results

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