PODCAST · society
My Worst Date
by 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.
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517
Mess Blind
This week Keegan, Cassi and Christina talk about the Shailene Woodley and Aaron Rogers situation as well as Hall Passes in general. Going into the bad dates, Cassi shares a date with a hoarder, Keegan shares a date with a presumptuous older man and Christina shares a date that rides an alcohol rollercoaster. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Benjamin Field. Learn more about your ad choices. Visit megaphone.fm/adchoices
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516
Tiddy Meat
This week Keegan, Cassi and Christina discuss California love and goodbyes as well as get real about what it's like to get a mammogram (spoiler: go get one, it's not that bad!) Going into the bad dates, Keegan share a date that is silent the whole time, Christina shares a date with a gaslighting d-bag and Cassi shares a church camp date with instant ick. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Alyssa Burkett. Learn more about your ad choices. Visit megaphone.fm/adchoices
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515
Shorty - 89
Join Keegan, Cassi and Christina for a bite-sized bonus episode! Hear the harrowing tale of the Milkman, and laugh along with terrible dates with crypto bros, potential axe murders, bad double dates and body malfunctions. Learn more about your ad choices. Visit megaphone.fm/adchoices
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514
All Living The Same Life
This week Keegan, Cassi and Christina talk about a tiktoker at the hot bartender's house listening to Lana on vinyl and how much trouble they're in. Also saying goodbye to two legends, Dolly & Tim. Going into the bad date stories, Christina shares a bulleted list of red flags, Keegan shares a date that wants couples therapy immediately and Cassi shares a story of a first blowjob. Christina wraps it up in the true crime segment, Tainted Love, with the story of Mica Miller. Learn more about your ad choices. Visit megaphone.fm/adchoices
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513
The Recap
This week Keegan, Cassi and Christina return for a breakdown of a tumultuous summer and talk about the Wicker trailer. Going into the bad dates, Cassi shares a date with a thief, Keegan shares a date that got scary pushy and the signs to pay attention to and Christina shares a guy that keeps putting his foot in his mouth. Cassi wraps it up in the true crime segment, Tainted Love with the story of Tim Smith. Learn more about your ad choices. Visit megaphone.fm/adchoices
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512
Tainted Love Movie - Beautiful Wedding (Replay)
Hi Worsties - promise this is the last one and we'll be back with a new episode next week! We have incredible updates coming your way as we navigate a very life-changing summer. But for now, enjoy the sequel to last week's episode where we review Beautiful Wedding, a movie so bad it will break your brain that it even got made. Learn more about your ad choices. Visit megaphone.fm/adchoices
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511
Getting Off The Floor
This week Keegan, Cassi and Christina talk about the ridiculous uptick in trad wife content and protecting women's right to vote. Going into the bad dates, we have a very surprising sex move, language barriers, a really gross dude apartment, a Dad on the lookout, mountain lions on night hikes and a fart button. Learn more about your ad choices. Visit megaphone.fm/adchoices
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510
Breaking News
This week Keegan, Cassi and Christina discuss the viral TikTok voicemail on whether it's a sign of informed consent or coercion. Going into the bad dates, there's dirty knives, feral cats, gross & unsafe dinner dates, Johnnie Walker and losing your date to your best friend. Learn more about your ad choices. Visit megaphone.fm/adchoices
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509
Shorty - 88
In this bite-sized episode, Keegan, Cassi and Christina talk about a Diet Coke conspiracy and never being a comfortable temperature, and share dates featuring a dude wanting a mommy, aggressive winking, conspiracy theories, moving too fast, Monster Trucks and fist bumps. Learn more about your ad choices. Visit megaphone.fm/adchoices
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508
Coq in a Van
This week Keegan, Cassi and Christina talk tampons and womanhood. Going into the bad dates, there's stories featuring diy tattoos lakeside, bucking broncos, running into exes, intoxication and crashing random family reunions. Learn more about your ad choices. Visit megaphone.fm/adchoices
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507
The Right Jazz
This week Keegan, Cassi and Christina talk mansplaining, jazz and Summer House drama. Going into the bad dates, there's one with the 13th cousin of Queen Elizabeth II, a date praying for strength against carnal temptations, real soap in the dishwasher mishaps, dates both too drunk AND racist at the same time and a Prom day fart to end all farts. Learn more about your ad choices. Visit megaphone.fm/adchoices
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506
What Those Horns Do
This week Keegan, Cassi and Christina talk about massages, Richard Simmons and beginning podcasting. Going into the bad dates, there are juice MLMs, lots of blood, toe-sucking in public, angels, drunken naps outside and anti-science catfishes. Learn more about your ad choices. Visit megaphone.fm/adchoices
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505
The Done Place
This week Keegan, Cassi and Christina talk FIFA patriotism, UFC and ballsmaxxing. Going into the bad dates, there's Australians, older woman dating fails, air guitars, 14 mile walks, dating friend of friend's ex and a wholesome binge watch of Twilight. Learn more about your ad choices. Visit megaphone.fm/adchoices
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504
Catch and Release
This week Keegan, Cassi and Christina discuss smoking sections, threads about shit in a bag and Stevie Wonder. Going into the bad dates, there's dates with fresh babies, dates that hate music, dates in car accidents and weird fetishes. Learn more about your ad choices. Visit megaphone.fm/adchoices
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503
Save Our Souls
This week Keegan, Cassi and Christina talk Summer House reunion drama and the back and forth of Keke Palmer & Sean Evans. Going into the bad dates, there are bedwetters, a first date in Patagonia, a date with a biter in a k-hole, hit and runs and a date that finds love with a friend. Learn more about your ad choices. Visit megaphone.fm/adchoices
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502
Shorty - 87
Join Keegan, Cassi and Christina in this bite-sized episode of bad dates, with stories featuring broke boys and baby traps, r/GirlDinnerDiaries, and the birthday dinner from hell. Learn more about your ad choices. Visit megaphone.fm/adchoices
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501
The Impossible Cigarette
This week Keegan, Cassi and Christina talk about betrayal - or what diabolical things an ex can do after breaking up. Going into the bad dates, Keegan shares an embarrassing one night stand, Christina shares a date less reliable than his drug dealer, and Cassi shares a date with a rap sheet that leads to serious trouble. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Cati Blauvelt. Check out and support the brave women who are fighting wildfires: https://www.grassrootswildlandfirefighters.com/women-in-wildland-fire Learn more about your ad choices. Visit megaphone.fm/adchoices
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500
I'll Pray For You
This week Keegan, Cassi and Christina talk about a TikToker who exposed her husband's infidelity...with her brother's wife. Then a special shout out to Brendan Fraser and a bonus FMK of his popular film roles. Going into the bad dates, Christina shares a date at a bar with someone underage, Keegan shares a date letdown by a hot lifeguard and Cassi shares a date trying way to hard too quickly. Christina wraps it up in the true crime segment, Tainted Love, with the story of Teresa Mayfield. Learn more about your ad choices. Visit megaphone.fm/adchoices
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499
All Forked Up
This week Keegan, Cassi and Christina talk Paul Hollywood's cat emergency as well as what to do in your 30s when you want kids but your partner is on the fence. Going into the bad dates, Cassi shares a date with mixed signals, Christina shares a date with a orthopedic referral and Keegan shares a date with some intense mommy issues. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Anne Boleyn of the band Hellion. Learn more about your ad choices. Visit megaphone.fm/adchoices
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498
Toxic Nerdery
This week Keegan, Cassi and Christina laugh about dating profile icks and reminisce about Myspace and early internet innocence. Going into the bad dates, Keegan shares a diabolical dating app trick to lure young girls, Cassi shares a date that needs a place to live 2 months in and Christina shares a date with a very shocking confession. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Kassanndra Cantrell. Learn more about your ad choices. Visit megaphone.fm/adchoices
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497
Shorty - 86
Join Keegan, Cassi and Christina in this bite-sized bonus episode featuring med-beds and antidepressants, ghosts and threesomes, celebs, stalking and diva behavior. Learn more about your ad choices. Visit megaphone.fm/adchoices
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496
Don't Be Nervous
This week Keegan, Cassi and Christina talk about bridesmaid drama for #jemily, Quinn App and Tinder in Germany. Going into the bad dates, Christina shares a bad date with a side of Sprite, Keegan shares a date with serious mental issues and Cassi shares a date with arrested development. Christina wraps it up in the true crime segment, Tainted Love, with the story of Chad Schipper. Learn more about your ad choices. Visit megaphone.fm/adchoices
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495
Bad Times
This week Keegan, Cassi and Christina talk about Keegan's latest misadventure along with the horrifying news about the online academy for men who want to abuse their partners. Going into the bad dates, Cassi shares a very mismatched date with someone who wants to ride the rails, Keegan shares a date who ghosts a whole vacation and Christina shares a common bad relationship miscommunication date. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Jason Corbett and Molly Martens. Learn more about your ad choices. Visit megaphone.fm/adchoices
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494
A Shared Experience
This week Keegan, Cassi and Christina talk about the unwarranted backlash against Aubrey Plaza as well as the new Netflix doc on Lamar Odom. The FMK is between Willie Nelson, Will Arnett and William Shakespeare. Going into the bad dates, Keegan shares a date pressuring drinks and more, Christina shares a date that didn't realize it was a date and Cassi shares a date that turns into love-bombing. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Barry Winchell. Learn more about your ad choices. Visit megaphone.fm/adchoices
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493
Boots on the Ground
This week Keegan, Cassi and Christina talk about Kristi Noem's husband, Keegan's cat attack and a listener correction about Peyton Manning. The FMK is between Michael Jordan, Meg Ryan and Nicholas Cage. Going into the bad dates, Keegan shares a date ruined by back acne, Christina shares a date ruined by cocaine and Cassi shares a date that pretends not to know what sex is. Book link for guy's wife: https://www.amazon.com/s?k=the+encore+juliet+izon&adgrpid=187375749018&hvadid=779554479816&hvdev=c&hvexpln=0&hvlocphy=9031167&hvnetw=g&hvocijid=10182825533073559311--&hvqmt=e&hvrand=10182825533073559311&hvtargid=kwd-2466471902575&hydadcr=10022_13483915_10819&mcid=1b96b4b1ac923be6bf6058057630c61e&tag=googhydr-20&ref=pd_sl_11j9c4o33f_e Learn more about your ad choices. Visit megaphone.fm/adchoices
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492
Shorty - 85
Join Keegan, Cassi and Christina for a bite-sized episode talking about Summer House drama, religious trauma dates, muppet kisses, running from the cops and crashing small parties. Learn more about your ad choices. Visit megaphone.fm/adchoices
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491
Catching Print
This week Keegan, Cassi and Christina discuss birthday shenanigans and the most unbelievable cake of all time. The FMK is between Freddie Mercury, Elton John and Peyton Manning. Going into the bad dates, Christina shares a date coming to terms with her advancing age, Cassi shares a wingwoman horror story and Keegan's shares a wild date at Walmart. Christina wraps it up in the true crime segment, Tainted Love, with the story of Ira Bernstein. Learn more about your ad choices. Visit megaphone.fm/adchoices
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490
Hollyweird
This week Keegan, Cassi and Christina talk weird opinions on ballet and opera and breakdown for this week's FMK of Judy Garland, Carrie Fisher and Billy Ray Cyrus. Going into the bad dates, Keegan shares a date that has to pretend to be family, Cassi shares a date that gets too smashed for The Notebook and Christina shares a date with a nerd night fail. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Sade Robinson. Learn more about your ad choices. Visit megaphone.fm/adchoices
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489
Gallows Humor
This week Keegan, Cassi and Christina discuss rich wishes and play FMK with Nathan Fillion, Alan Tudyk and Kyle McLaughlin. Going into the bad dates, Cassi shares a date with one disaster after another, Christina shares a catfish date that tries to score and Keegan shares a date with no clue why their surprise is terrifying. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sharon Kinne. Learn more about your ad choices. Visit megaphone.fm/adchoices
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488
A Whole Timmy Chalamet
This week Keegan, Cassi and Christina talk about AI relationships and the state of dating apps. The FMK is between Timothy Chalamet, Katy Perry and Chelsea Handler. Going into the bad dates, Christina shares a date that spends the rest of their life trying to escape, Keegan shares a date with a conspiracy theorist and Cassi shares a date at a puppet festival. Christina wraps it up in the true crime segment, Tainted Love, with the story of Rob Metzer. Learn more about your ad choices. Visit megaphone.fm/adchoices
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487
Good For Jazz
This week Keegan, Cassi and Christina talk Alpine Divorce and conspiracy theories. The FMK is between Jennifer Garner, Steve Buscemi and Yoko Ono. Going into the bad dates, Cassi shares a date that just hangs out all day, Keegan shares a terrifying newspaper date and Christina shares a rollercoaster date with wine and coke. Cassi wraps it up in the true crime segment, Tainted Love, with the story of Sophia Dorothea of Celle. Learn more about your ad choices. Visit megaphone.fm/adchoices
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486
Shorty - 84
Join us in a bite-sized episode featuring healthcare and drugs, foot lickers, zits, egg lovers and beta testing apps for the zombie apocalypse. Learn more about your ad choices. Visit megaphone.fm/adchoices
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485
Anything Goes
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 Affair. Learn more about your ad choices. Visit megaphone.fm/adchoices
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484
Find Local Bad Bunnies In Your Area
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 megaphone.fm/adchoices
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483
Waka Waka
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. Visit megaphone.fm/adchoices
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482
Breadwinners and Breadlosers
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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481
Weirds and Icks
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 megaphone.fm/adchoices
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480
A Cannon Event
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 choices. Visit megaphone.fm/adchoices
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479
Surviving...
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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478
Don't Talk No Sh*t
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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477
Movie Review - When Harry Met Sally
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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476
Loser Behavior
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 megaphone.fm/adchoices
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475
Everything Sucks
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, Tainted Love, with the story of Blazej Kot. 15% off at https://uncommongoods.com/worstdate Learn more about your ad choices. Visit megaphone.fm/adchoices
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474
F*ck, Marry, Second Husband
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 crime segment, Tainted Love, with the story of Ryan Borgwardt. Learn more about your ad choices. Visit megaphone.fm/adchoices
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473
Shorty - 83
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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472
Holiday Movie Review: Hot Frosty
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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471
Too Stupid to Live ft. Keegan & Christina
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 postpone recording regular episodes of My Worst Date. We'll be back with regular episodes on 12/10 and appreciate your patience and understanding! Learn more about your ad choices. Visit megaphone.fm/adchoices
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470
Getting Stuffed
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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469
Challenge Accepted
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 https://beducate.me/worstdate69 and use code worstdate69 for 65% off your yearly pass—that’s just $69 for the whole year, locked in for life. Learn more about your ad choices. Visit megaphone.fm/adchoices
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468
I'll Load Your Dishwasher
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 Cornell. Learn more about your ad choices. Visit megaphone.fm/adchoices
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ABOUT THIS SHOW
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.
HOSTED BY
My Worst Date Podcast LLC
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