The Dating Debrief – Details, episodes & analysis

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

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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.

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.

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This week, Casey finally has her long-awaited one-on-one hang with the mysterious cowboy. He comes over to fix her bike, but the evening leads to much more. But as the girls unpack every detail, the conversation takes an unexpected turn into something much bigger: why we hold onto potential, how many chances someone deserves, and whether waiting for people to become who we hope they'll be ever actually works out. 

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The girls are back with a brand new dating debrief! After their conversation with matchmaker Alessandra last week, Casey decided to fully lean into putting herself out there and dropping her handkerchief, starting with a singles event that promised flirty fun but quickly turned into complete chaos. Then, she shares the story of a spontaneous date with an out-of-towner that somehow spirals into an awkward, surreal night filled with unexpected pool games, mixed signals, and zero chemistry. Plus, there’s finally an update on the mysterious cowboy as Casey debates whether this ongoing flirtation could actually become something more, or if it’s a disaster waiting to happen.

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After a rough week and a brief pause from dating, Casey and Rachel sit down with celebrity matchmaker Alessandra Conti for an unfiltered deep dive into modern romance, dating burnout, and why finding love in Los Angeles can feel impossible. Alessandra breaks down the patterns keeping both women stuck in chaotic dating cycles, and offers honest advice about chemistry, commitment, and the kinds of men they should actually be looking for. The conversation gets hilariously candid as the girls unpack past flings, dating app disasters, emotional attachment, and the difference between exciting love and stable love, all while Alessandra attempts to map out their romantic futures in real time.  

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Coming off of the break up with Trinket Tom, this week Rachel and Casey sit down with clinical psychologist Dr. Pamela Varady for an honest and emotional conversation about attachment styles, emotional unavailability, self-worth, and why Casey can’t seem to make it past the fourth date. Together, they unpack the difference between chemistry and true connection, the addictive pull of emotionally unavailable partners, and the fear of vulnerability that can hide beneath a “go with the flow” attitude. Dr. Varady leaves Casey with practical tools for dating differently, protecting her inner child, and finally learning how to let herself be truly seen.

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