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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Contact path
Verified email
Booking probability
38%
Guest openness
Selective
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Signup to Generate a PitchEver 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.
Recent episodes include "Asbestos Blankets" (28 October 2026, 81 minutes), "Literal Demon" (14 October 2026, 90 minutes), and "The Anger Episode" (7 October 2026, 95 minutes).
My Worst Date publishes roughly weekly, with episodes averaging 67 minutes across 525 episodes.
Booking probability for My Worst Date is 38%, and the host is rated Selective on guests. My Worst Date requires a Pod Score of 89 or higher. My Worst Date's contact route on record: verified email.
My Worst Date is a society podcast with 525 episodes published.
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My Worst Date
This week Keegan, Cassi and Christina talk about the Shane Gillis monologue and Love Is Blind ghosting incident. Going into the bad dates, Cassi shares a date upset with too much talk about an ex, Christina shares an 18...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
My Worst Date
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...
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