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Relationships · My Worst Date Podcast LLC

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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Latest episodes

Showing 20 · updated from the feed

Rich Fantasy Life

This week Keegan, Cassi and Christina talk about Keegan's journey to her new home and the H3 podcast drama. Going into the bad dates, Christina shares a list of bad Aus

Nov 4
1 h 02 min

Shorty - 91

Join Keegan, Cassi and Christina for this bite-sized episode featuring Halloween shenanigans, and bad dates high on shrooms, holiday butt plugs, bbqs & number twos, bumps

Nov 2
31 min

Asbestos Blankets

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

Oct 28
1 h 21 min

Here Comes The Hurricane

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 fol

Oct 21
1 h 23 min

Literal Demon

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, Chris

Oct 14
1 h 30 min

The Anger Episode

This week Keegan, Cassi and Christina discuss the online discourse around the sexual assault lawsuit and investigation involving Cornell University and seven fraternity m

Oct 7
1 h 34 min

Shorty - 90

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

Oct 5
32 min

Night Pills

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 t

Sep 30
1 h 45 min

Shed

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, Cas

Sep 23
1 h 39 min

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 shar

Sep 16
1 h 25 min

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

Sep 9
1 h 26 min

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 a

Sep 7
34 min

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 t

Sep 2
1 h 24 min

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

Aug 26
1 h 24 min

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

Aug 19
31 min

Tainted Love Movie Review: Beautiful Disaster

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 Beauti

Aug 12
43 min

Kissing - Why Do We Do That??

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

Aug 5
57 min

Pass The Baton

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 coloni

Jul 29
57 min

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

Jul 22
55 min

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 k

Jul 15
59 min

Chart positions

Where My Worst Date ranks today in each Apple Podcasts chart (US, Nov 6, 2026).

#161 NEW Relationships US

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About My Worst Date on Reason.fm

Here you find the Apple Podcasts chart positions of My Worst Date, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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