My Worst Date

My Worst Date

My Worst Date Podcast LLC
Country USA
Language EN-US
Episodes 525
Latest 21.10.2026

My Worst Date is a comedy and relationship podcast hosted by best friends Keegan Winfield, Christina Conner, and Cassi Young-Paxton. The hosts discuss pop culture, relationships, and true crime while sharing their own dating disasters and stories submitted by listeners. Episodes center on crazy bad dates and the awkward, funny, and sometimes cringe-inducing experiences that come with dating.

Episodes

  • Here Comes The Hurricane 21.10.2026 1h 23m
    This week Keegan, Cassi and Christina dive into controversy: whether or not the man should pay on the first date. Going into the bad dates, Keegan shares a date that followed to a second location looking for confrontation, Christina shares a date too eager for some kind of closure and Cassi shares a date that makes a post-dating fail tiktok. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Kerstin Gurtner. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Literal Demon 14.10.2026 1h 30m
    This week Keegan, Cassi and Christina discuss the new sexually transmitted diarrhea, the plague and a woman married to a cheating pillow. Going into the bad dates, Christina shares a date with a list of standards, Keegan shares a date with zero empathy for his ex and kid, and Cassi shares a date with a close cousin. Christina wraps it up in the true crime segment, Tainted Love, with the story of Kari Baker. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • The Anger Episode 07.10.2026 1h 34m
    This week Keegan, Cassi and Christina discuss the online discourse around the sexual assault lawsuit and investigation involving Cornell University and seven fraternity members. Going into the bad dates, they're all awful and the anger just builds - from lack of ambition to pushing boundaries to absolute monster behavior. And then Cassi wraps it up in the true crime segment, Tainted Love, with the unsolved story of Angela Green. If you know anything about the disappearance of Angela Green, please contact the Prairie Village PD at 913-642-6868 or Crime stoppers tip line at 816-474-8477. If you or someone you know has been affected by sexual assault, confidential support is available 24/7 through the National Sexual Assault Hotline at 1-800-656-4673 or online at rainn.org. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Shorty - 90 05.10.2026 32m
    Join Keegan, Christina and Cassi in this bite-sized episode full of nostalgia and Pier One Imports and dates featuring neglectful dads, constructive criticisms, and lots of ghosts. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Night Pills 30.09.2026 1h 45m
    This week Keegan, Cassi and Christina talk about new Taylor Swift music, AI love cons and New York City. Going into the bad dates, Keegan shares a date that turned into therapy, Cassi shares 4 bad dates in one, and Christina shares a list of gross boyfriend hygiene. Keegan wraps it up in the true crime segment, Tainted Love, with the story of Mindi Kassotis. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Shed 23.09.2026 1h 39m
    This week Keegan, Cassi and Christina talk about unleased boyfriends and Chicago. Going into the bad date stories, Christina shares a date with a guy who hates women, Cassi shares a date with MAHA and Keegan shares a date with a rich guy in a shed. Christina wraps it up in the true crime segment, Tainted Love, with the story of Mark Shaver. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Mess Blind 16.09.2026 1h 25m
    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
  • Tiddy Meat 09.09.2026 1h 26m
    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
  • Shorty - 89 07.09.2026 34m
    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
  • All Living The Same Life 02.09.2026 1h 24m
    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
  • The Recap 26.08.2026 1h 24m
    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
  • Tainted Love Movie - Beautiful Wedding (Replay) 19.08.2026 31m
    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
  • Tainted Love Movie Review: Beautiful Disaster 12.08.2026 43m
    Hi Worsties! Our episode this week was beset with wildfires, power outages and major sinus infections so please enjoy one of our favorite terrible movie reviews of Beautiful Disaster. Seriously recommend hate watching this on Amazon Prime or just listen to us tear it to shreds. Real ones know we also reviewed the sequel, Beautiful Wedding, which was somehow even worse, and you can access them all by subscribing to our Patreon here: https://patreon.com/myworstdate?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_creator&utm_content=copyLink Back next Wednesday with a fresh episode in your feed, and thank you all so much for listening! Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Kissing - Why Do We Do That?? 05.08.2026 57m
    This week Keegan, Cassi and Christina talk about the prevalence of men leaving their sick partners and Doctor misbehaviors. Going into the bad dates, there are stories featuring littering, being stood up after several texts, rejected kisses and crying, boxing, dates trying to borrow change and cigarettes, and peepad accidents. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Pass The Baton 29.07.2026 57m
    This week Keegan, Cassi and Christina talk Jimothy and crow friends as well as My Strange Addiction. Going into the bad dates, there's cheating on Snapchat, artist colonies, stomach issues, widows and Bigfoot. Learn more about your ad choices. Visit megaphone.fm/adchoices
  • Getting Off The Floor 22.07.2026 55m
    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
  • Breaking News 15.07.2026 59m
    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
  • Shorty - 88 13.07.2026 30m
    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
  • Coq in a Van 08.07.2026 53m
    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
  • The Right Jazz 01.07.2026 1h 2m
    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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