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The Dating Debrief

Dear Media 8 episodes Latest May 28, 2026

The Dating Debrief is a dating podcast hosted by former Bachelor star Rachel Recchia. Each season follows one single woman as she goes on 13 first dates, but instead of hearing the dates themselves, listeners get the post-date debrief where she spills everything—the sparks, red flags, awkward moments, and texts that never came. A team of experts helps decode modern dating chaos, from swiping strategies to relationship patterns. It's part social experiment, part girls' night gossip, offering a front-row seat to the highs, lows, and drama of trying to find love today.

Episodes

Casey: Dates 9 & 10 (Speed Dating & Teacher Trish) Jun 11, 2026 00:38:22 This week Casey fully commits to her mission of dating outside her comfort zone, leading to one of her busiest (and most chaotic) weeks yet. First, she takes the leap and attends a queer speed dating event, where she's swept up in unexpected connections, surprising chemistry, and one particularly unforgettable encounter. But after chasing an undeniable spark, Casey finds herself on a very

Casey: Date 8 (The Cowboy) Jun 4, 2026 00:35:16 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

Casey: Date 7 (Singles Party and Out of Towner Todd) May 28, 2026 00:37:24 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

Casey: Date 6 (The Matchmaker) May 21, 2026 00:39:12 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 k

Casey: Date 5 (The Therapist) May 14, 2026 00:49:58 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 emoti

Casey: Date 4 (The 4th Date Curse) May 7, 2026 00:49:47 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 tat

Casey: Date 3 (Poison Ivy & The Algorithm) Apr 30, 2026 00:39:43 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

Casey: Date 2 (Trinket Tom) Apr 23, 2026 00:36:38 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 gen

Casey: Date 1 (The Evangelical Ghoster) Apr 16, 2026 00:31:01 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 Chin

The Dating Debrief: Coming April 16th! Apr 9, 2026 00:01:06 Produced by Mollie Biskar & Soft Skills Media, in association with Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Dating Debrief

Episodes

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