The Dating Debrief

On this episode of the Dating Debrief, Casey is forced to confront the slow unraveling of her connection with Trinket Tom after a disappointing New Year’s Eve leaves her questioning whether chemistry and consistency can ever truly coexist. As Rachel and Casey unpack ghosting, mixed signals, and the emotional exhaustion of modern dating, a mysterious new “cowboy” enters the picture — a tattooed musician with perfect timing, confusing energy, and just enough intrigue to spark hope again.

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On this episode of The Dating Debrief, Casey returns with updates on both Poison Ivy and Trinket Tom — including a chaotic first date full of Muppet fan edits, awkward chemistry, and a steamy make out outside a bar, contrasted with a whirlwind third date that starts with ramen and ends with after-parties, wine bars, and growing feelings.

Then, former Bumble Head of Data Analytics Candace Ren joins the show to break down the truth about dating app algorithms, “rose jail,” profile optimization, ghosting penalties, and why Casey’s Hinge profile might be attracting the wrong people entirely.

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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.

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

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.

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

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.