Messy life, sharp friends, rom-com instincts.
My Worst Date turns casual friend-chat into sharp comedy about the awkward, personal, and culturally weird. Episodes move from Hollywood chatter and romantic-comedy comfort films to perimenopause, astrology, edibles, illness, and public hypocrisy.
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My Worst Date is a candid friend-table show with a pop-culture engine and a relationship-show frame. Cassie, Keegan, and Christina move quickly, often starting from one personal detail and letting the conversation widen into a larger cultural gripe. It is funny first. Then it gets specific. Recent episodes make room for Hollywood awards chatter, When Harry Met Sally, public hypocrisy, astrology, women’s health, illness, birthdays, and the strange social physics of edibles. The pace feels unfiltered without becoming shapeless. Someone drops a detail; someone else catches the absurdity; the room turns it into a story. That is the show’s core pleasure. It can spend time on a rooftop Hollywood birthday and still sound like the listeners are sitting close enough to hear the side comments. It can talk about perimenopause with the weary humor of people who are tired of vague medical answers. It can treat astrology as both a joke and a useful language for talking about ambition, money, and personality. Its movie-review episodes add a more structured lane. When Harry Met Sally becomes less a museum piece than a prompt for talking about friendship, romance, memory, and comfort movies people never quite outgrow. The tone is adult and blunt. The politics appear through reaction rather than lecture, especially when the speakers call out hypocrisy around public behavior and private life. The show is at its best when a small anecdote opens into something more recognizable: body frustration, social anxiety, pop-culture fixation, or the private comedy of getting through a rough week. It suits listeners who want sharp, familiar conversation rather than a tidy advice format. The result is messy in the intentional way good friend conversations are messy: quick, funny, personal, and occasionally unexpectedly revealing.
Made for: For listeners who like candid banter about relationships, pop culture, bodies, movies, astrology, and everyday chaos. It especially fits fans of conversational comedy that can swing from silly to pointed without losing warmth.
What sets it apart: The show blends dating-show DNA with a wider friend-chat format, making room for romantic comedies, Hollywood gossip, women’s health, astrology, and blunt social commentary. Its strength is the lived-in chemistry between Cassie, Keegan, and Christina.
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.
Short reviews from the PlayNext desk, based on the episodes we processed.
A tiny corner of edible cake becomes a sharply funny spiral through weed anxiety, bad timing, and California health care ads.
A tiny corner of edible cake sends My Worst Date into weed anxiety, bad timing, and the brain's gift for turning background noise into catastrophe.
A warm, loose revisit to Harry and Sally, where familiar scenes lead into friendship talk and remembered relationships.
When Harry Met Sally gives the My Worst Date hosts a natural path back into the movie's central friendship question, as Harry and Sally keep circling each other after arguing that men and women cannot really be friends.
A candid episode where family diet memories turn into sharp, affectionate jokes about bodies and celebrity chemistry.
Black & White Cookie starts with a TikTok about "almond moms" and the casual ease some mothers have around commenting on weight and bodies. Cassie ties it to doing SlimFast and Special K diets with her mother in high school, and the conversation keeps affection and criticism in…
Three friends recap Daredevil, Fallout, and new releases scene by scene, in Spanish.
Slasher talk with sharp teeth.
Hosts Cassi, Keegan, and Christina open by discussing 'almond moms' and how childhood messages about weight and bodies create lasting shame.
Hosts Keegan Winfield and Christina Conner review the 1989 romantic comedy 'When Harry Met Sally'.
My Worst Date’s “Boots on the Ground” combines commentary about Kristi Noem’s husband, listener dating disasters, and the hosts’ own stories about cat injuries and romantic mishaps.
My Worst Date: Shorty - 85 pairs Cassie, Keegan, and Christina's perimenopause discussion with listener stories about dates involving a dark park, religious conflict, and a stolen car.
My Worst Date hosts Keegan and Christina recount a Hollywood rooftop birthday party where a delayed cake arrived missing a piece and guests were given plastic cups and straws instead of plates and forks.
Cassie, Keegan, and Christina debate celebrity opinions about cats, ballet, opera, theater, and Timothy Chalamet’s claim that audiences do not care about some live art forms.
A group of friends discuss astrology, focusing on the meaning of having Jupiter, Saturn, and Pluto in the second house and what it indicates about wealth.
My Worst Date hosts Cassie, Keegan, and Christina discuss mental-health treatment, healthcare access, cannabis reactions, and listener-submitted dating disasters.
The hosts of My Worst Date podcast discuss being sick with the flu and not being able to record.
A podcast episode reviewing the movie When Harry Met Sally, discussing its themes and legacy, with a focus on the question of whether men and women can be friends.
The hosts discuss a Reddit post about a man who discovers his wife's family cyberbullied him and his wife hid it.
The hosts of My Worst Date share a Patreon-exclusive review of the holiday movie Hot Frosty to kick off the holiday season.
A podcast episode where the hosts review a book called Renegade Love and discuss their holiday plans, with a focus on silliness and anatomy questions.