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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

36:40

Shorty - 76

My Worst Date ·

2025/03/03

In this month's bite-sized episode, Keegan, Cassi and Christina talk about what's in the box and unique revenue opportunities, and laugh about bad dates containing bats, lice, tampons, NDAs and seashells. Learn more about your ad choices. Visit megaphone.fm/adchoices

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87:07

Lock Your Doors

My Worst Date ·

2025/02/26

This week Keegan, Cassi and Christina talk about low stakes TV and Bridezilla tantrums. The FMK is between Elliot Page, Steve Irwin and Freddie Prinze Jr.Going into the bad dates, Keegan shares a date with a 5'3" fancy man, Cassi shares a date with lemon juice in the eye, and Christina shares a date with a stalker ex....or is it? Keegan wraps it up in the true crime segment, Tainted Love, with the story of Ermalinda Palomo and Nathaniel Huey Jr. Learn more about your ad choices. Visit

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96:29

Teenage Nightmares

My Worst Date ·

2025/02/19

This week Keegan, Cassi and Christina discuss Valentine's day adventures and play FMK with Sterling K. Brown, Kendrick Lamar and Quinta Brunson.Going into the bad dates, Christina shares a date in his mom's bedroom, Cassi shares a date at Hooters and Keegan shares a diabolical scheme of date involving fake identities and exes. Christina wraps it up in the true crime segment, Tainted Love, with the story of Daisy Coleman. Help prevent sexual violence in teens by supporting https://safebae.org/ Learn

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91:14

We Are Not Liable (Nor Are We Well)

My Worst Date ·

2025/02/12

This week Keegan, Cassi and Christina talk about conference culture and Linkedin. The FMK is between Bloody Marys, Mimosas and Old Fashioned.Going into the bad dates, Cassi shares a shame receipt with soup, Christina shares a sushi mishap and Keegan shares a date with too many shots. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Mei Haskell. Learn more about your ad choices. Visit megaphone.fm/adchoices

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92:55

You Are The Drama

My Worst Date ·

2025/02/05

This week Keegan, Cassi and Christina talk baby season and "we're pregnant" posts, and play FMK with party cities Nashville, Miami and Vegas.Going into the bad dates, Keegan shares a text to the wrong person, Christina shares a no drama date that makes a bad comment and Cassi shares a text in the work chat you could never live down. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Farah Fratta. Learn more about your ad choices. Visit megaphone.fm/adchoices

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32:29

Shorty - 75

My Worst Date ·

2025/02/03

In this bite-sized episode, Keegan, Cassi & Christina discuss fully failing at new year resolutions, laugh about mistaken identities, cringe at a bad movie pick for a first date , talk about silly arguments and gasp about a surprise shoe thief and a man in disguise. Learn more about your ad choices. Visit megaphone.fm/adchoices

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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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