In this episode, the debrief couch is buzzing as Casey returns with a whirlwind update on her budding romance with Trinket Tom- a charming Hinge match whose thoughtful trinket exchange turns into two surprisingly magical dates filled with laughter, chemistry, and a few steamy bar make outs. But as the sparks fly, subtle shifts in texting patterns leave Casey questioning whether it’s a genuine connection or the early signs of inconsistency. After the Date Debrief we are joined by her best friend, Maura, who has been tasked with setting Casey up on a date that might just push her out of her comfort zone, and into something entirely new.

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Welcome to Season 1, Episode 1 of The Dating Debrief! This season we will follow Casey, a self-proclaimed hopeless romantic with a soft spot for emotionally unavailable men and a bad habit of getting in her own way. She's done the situationships, she's ignored the red flags, and she's ready to finally break the cycle.

Date one kicks things off with a bang — a wine-soaked night in Chinatown with a possibly evangelical stranger who opens doors, pays for everything, dances in the rain, and then... doesn't text back. Naturally.

Twelve dates to go. Let the experiment begin!

Produced by Mollie Biskar and Caoimhe McGurrin

In Association with Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Produced by Mollie Biskar & Soft Skills Media, in association with Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.