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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

88:09

There's Still Time

My Worst Date ·

2024/09/04

This week Keegan, Cassi and Christina discuss the app Timeleft and rumors about Meryl Streep and Martin Short. The FMK is between Steve Martin, Dana Carvey and Dan Ackroyd.Going into the bad date stories, Cassi shares a date with a super controlling dude, Christina shares an accidental date at a strip club and Keegan shares a rollercoaster of a date with magic tricks, mansplaining and soaking. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Brad McGarry. If you have a

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102:37

Vibes & Votes

My Worst Date ·

2024/08/28

This week Keegan, Cassi and Christina discuss how to determine if a coworker likes you, decentering relationships and the DNC. The FMK is between Ludacris, Keke Palmer and Chris Pine.Going into the bad dates, Keegan share a date that quickly feels unsafe, Cassi shares a date at the airport and Christina shares a date with serious tummy trouble. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Deborah Waldinger. If you have a story to share, reach out to us at

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95:11

Hot Ranch Mouth

My Worst Date ·

2024/08/21

This week Keegan, Cassi and Christina discuss Secret Lives of Mormon Wives and Blake Lively drama. The FMK is between Ralph Fiennes, Owen Wilson and Matthew McConaughey.Going into the bad dates, Christina shares a double date with a side of ranch, Cassi shares a bad comedy club date and Keegan shares a New Year's date with a random family. Christina wraps it up in the true crime segment, Tainted Love, with the story of Elaine O'Hara. Learn more about your ad choices. Visit

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92:40

Bad Reenactments

My Worst Date ·

2024/08/14

This week Keegan, Cassi and Christina talk about things they faked liking in past relationships and play FMK with Maya Rudolph, Charlize Theron and Sandra Bullock.Going into the bad dates, Cassi shares a terrifying date that went too deep into the investigation, Keegan shares a date with all the worst opinions and Christina shares a date that may be on Dateline soon. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Peter Bergna. Got a bad date to share? Go to

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84:51

Solely For Pics

My Worst Date ·

2024/08/07

This week Keegan, Cassi and Christina discuss Olympic village beds and hooking up along with wondering how to start making money off feet pics. The FMK is between Jude Law, Benjamin Bratt and Eric Bana.Going into the bad dates, Keegan shares a blind date with no chance, Christina shares a date with someone involved in an affair and Cassi shares a date with an absolute sadist. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Jeffrey Allan Maxwell. Got a bad date to

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36:19

Shorty - 71

My Worst Date ·

2024/08/05

Bite-sized bonus episode coming for you, filled with random thoughts on the Olympics and VP pics and bad dates with cheapskates, drunken fools at company picnics, toe shoes, and Cinemax.Learn more about your ad choices. Visit megaphone.fm/adchoices

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88:44

No Popcorn

My Worst Date ·

2024/07/31

This week Keegan, Cassi and Christina talk about feeling hope again and the Ballerina Farm article. The FMK is between Michael Phelps, Simone Biles and LeBron James.Going into the bad dates, Christina shares a date with wrong opinions and a giant poster, Keegan shares a date with a pushy, selfish jerk and Cassi shares a date that mom set up. Christina wraps it up in the true crime segment, Tainted Love, with the story of Joan Robinson Hill. Got a bad date to share? Go to

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83:02

Skibidi Toilet Ohio Rizz

My Worst Date ·

2024/07/24

This week Keegan, Cassi and Christina talk about AI dating apps and Gen Z flirting skills. The FMK is between Siri, Alexa and Cortana.Going into the bad dates, Cassi shares a date with a guy who ghosted for a good reason, Keegan shares a date from a bus stop and Christina shares a date that goes from kite flying to XXX. Cassi wraps it up in the true crime segment, Tainted Love with the story of Earl Taylor. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on Instagram,

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89:08

Match My Freak

My Worst Date ·

2024/07/17

This week Keegan, Cassi and Christina talk about a guy suing Apple because his wife caught him cheating. The FMK is between Katy Perry, Martha Stewart and Seth Meyers.Going into the bad dates, Keegan shares a date with a racist, Cassi shares a date with a younger, immature guy and Christina shares a date with a dirty secret. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Kimberly Dobbie. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on

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98:02

Loose on the Lips

My Worst Date ·

2024/07/10

This week Keegan, Cassi and Christina talk about the guy who chose his girl best friend over his fiancee and question how often to wash your bra - really. The FMK is between Christoph Waltz, Heidi Klum and David Hasselhoff.Going into the bad dates, Christina shares a date with a non-stop texter, Keegan shares a date who spews and goes in for the kiss, and Cassi shares a date who accidentally helps to commit a crime. Christina wraps it up in the true crime segment, Tainted Love, with the story of

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88:12

My Lips Are Sealed

My Worst Date ·

2024/07/03

This week Keegan, Cassi and Christina talk about @boyroom on TikTok spotlighting terrible boy rooms. The FMK is between Leonardo DiCaprio, Orlando Bloom and Jake Gyllenhaal.Going into the bad dates, Cassi shares a date with crack, Keegan shares a date with a messy eater and Christina shares a date that almost burnt the house down. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Cherica Adams. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on

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38:13

Shorty - 70

My Worst Date ·

2024/07/01

This week it's just Keegan and Christina, talking about Gen Alpha slang, bad dates with pimples and poop and communal hot tubs...we miss you Cassi! If you have a terrible date story to share, go to https://myworstdatepodcast.com or follow us on Instagram, YouTube and TikTok @myworstdatepodcast. Learn more about your ad choices. Visit megaphone.fm/adchoices

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88:35

Dive Bar Shenanigans

My Worst Date ·

2024/06/26

This week Keegan, Cassi and Christina talk about the new fungal STD and dive bar behaviors. The FMK is between Elijah Wood, Daniel Radcliffe and Tom Holland.Going into the bad dates, Keegan shares a second date proposal, Cassi shares a date getting too defensive and Christina shares a date with the wrong twin. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Lauren Astley. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on Instagram, TikTok &

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84:43

A Second Opinion

My Worst Date ·

2024/06/19

This week Keegan, Cassi and Christina talk House Hunters International and bad joke problems in a relationship. The FMK is between bananas, zucchini and English cucumbers.Going into the bad date stories, Christina shares a date who hates everything except Ryan Gosling, Keegan shares a guy who can't stop farting and Cassi shares a date that wants to get stomped on. Christina wraps it up in the true crime segment, Tainted Love, with the story of Katie Dugan. For more information about your

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88:05

Chase Dreams, Not Men

My Worst Date ·

2024/06/12

This week Keegan, Cassi and Christina discuss what NOT to do when you get ghosted and how no response is a response. The FMK is between Katya Zamolodchikova, Chappell Roan and Nina West.Going into the bad dates, Cassi shares an awful date with an anti-masker, Keegan shares a date with a controlling a-hole and Christina shares a date where mom ruins everything. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Laura Ackerson. Got a bad date to share? Go to

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81:12

Hot Stepmom Summer

My Worst Date ·

2024/06/05

This week Keegan, Cassi and Christina discuss the marathon mom, Harrison Butker and internalized misogyny. The FMK is between Queen Latifah, Vince Vaughn, and Jason Momoa.Going into the bad dates, Keegan shares a date with conspiracies, Christina shares a date with delusions and Cassi shares a date with an overconfident man in a shack. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Spencer Hight. Got a bad date to share? Go to https://myworstdatepodcast.com or follow

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32:07

Shorty - 69

My Worst Date ·

2024/06/04

Oooh boy, this one's unhinged!! The ladies discuss bad dates, cringe middle school moments, what happens when guys use the bathroom and what you DON'T want to find in your friends' bathrooms. Have fun!!!

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106:24

Hot Rodent Boyfriend

My Worst Date ·

2024/05/29

This week Keegan, Cassi and Christina talk sports and sexy rat boyfriends. The FMK is between Tom Hiddleston, Josh O'Connor and Benedict Cumberbatch.Going into the bad dates, Christina shares a date with a terrible car, Keegan shares a date that blows up every channel, and Cassi shares a date with 9 cats. Christina wraps it up in the true crime segment, Tainted Love, with the story of Dr. John Schneeberger. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on Instagram,

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122:33

Put It Behind a Paywall

My Worst Date ·

2024/05/20

This week Keegan, Cassi and Christina talk more MILF Manor and second hand embarrassment, then play FMK with Milo Ventimiglia, Kendrick Lamar and Robert Pattinson.Going into the bad dates, Cassi shares a hungover date at church, Christina shares a date with the most confidence and Keegan shares a date more interested in the roommate. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Suzan and Michael Bear. Got a bad date to share? Go to https://myworstdatepodcast.com or

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105:54

The Most Chaotic Booth at Applebee's

My Worst Date ·

2024/05/15

This week Keegan, Cassi and Christina talk about MILF Manor 2 and AI Dating. The FMK is between Tiffany Pollard, Cynthia Bailey, and Jonathan Van Ness.Going into the bad dates, Keegan shares a Tinder date that's actually a couple, Cassi shares a frugal date at Applebee's and Christina shares a sailing date with lots of rum. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Erica &. BJ Sifrit. Got a bad date to share? Go to https://myworstdatepodcast.com or follow us on

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494 results

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