The Dating Debrief

Epizódok

• Casey: Bonus Episode (Casey Returns) 16.07.2026 19p

  In this special bonus episode, Casey returns to the cheetah couch a few months after her season finale to fill us in on everything we’ve missed…including the shocking return of a familiar name! Then we meet our new bachelorette Sydney, who joins Rachel and Casey for a mini debrief about a very peculiar situation in her current dating life. Before officially passing the baton, Casey shares some of her hard-earned advice for Sydney as she begins her own journey. Thank you for listening this season and be sure to follow us on Instagram @datingdebriefpodcast so you don't miss the Season 2 premiere announcement! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 14 (The Psychic) 09.07.2026 33p

   As Casey's dating experiment comes to a close, she and Rachel look back on everything they've learned over thirteen unforgettable first dates, from unexpected connections and disappointing dead ends to the confidence that comes from trusting your own instincts. Then, they're joined by a special guest who offers a fresh perspective on the patterns, lessons, and possibilities that have shaped Casey's journey. It's a heartfelt, funny, and hopeful finale, but make sure to come back next week for one final update from Casey, and an introduction to our next bachelorette!  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 13 (The Johnny Depp Wannabe) 02.07.2026 43p

  This week, Casey returns from a weekend away with a fresh perspective on dating, and quickly finds herself thrown back into the chaos. As one connection quietly fizzles, another takes an unexpected turn after a surprising lesson in setting boundaries. Then, a string of wildly different first dates introduces an unforgettable cast of characters, from a man whose confidence far outweighs his self-awareness to a mysterious stranger who seems to step straight out of a movie. Rachel and Casey unpack why chemistry isn't always enough, whether exes deserve another chance, and how trusting your instincts can save you from wasting time on the wrong people. Just when it feels like the season couldn't get any wilder, the stage is set for one final adventure.   See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 12 (Extra Credit with Teacher Trish) 25.06.2026 32p

  This week, Casey finds herself caught between fantasy and reality as her dating journey takes a few unexpected turns. There's an update on the mysterious cowboy, another date with Teacher Trish that challenges everything Casey thought she knew about chemistry, and a surprise new connection that arrives in the most unexpected place. Along the way, Rachel and Casey unpack whether butterflies are really the best indicator of compatibility, why slow-burn attraction can feel so unfamiliar, and what it actually looks like to break old dating patterns. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 11 (The Cowboy Returns) 18.06.2026 33p

  This week, Casey finds herself caught between two very different romantic possibilities. While things continue to slowly unfold with Teacher Trish, an undeniable connection with the mysterious Cowboy reaches a turning point, forcing Casey to confront the difference between chemistry, compatibility, and fantasy. As she and Rachel unpack attraction, attachment, and the stories we tell ourselves about the people we're drawn to, they explore a question every dater eventually faces: how do you enjoy a connection for what it is without losing sight of what you actually want? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Dates 9 & 10 (Speed Dating & Teacher Trish) 11.06.2026 38p

  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 different kind of date with a kind, grounded school teacher - forcing her to confront an uncomfortable question: Is she mistaking intensity for compatibility? Rachel and Casey unpack the difference between instant attraction and slow-burning potential while exploring the dating dilemma so many people face: are we chasing excitement, or are we actually looking for something real?   See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 8 (The Cowboy) 04.06.2026 35p

  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.  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 7 (Singles Party and Out of Towner Todd) 28.05.2026 37p

  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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 6 (The Matchmaker) 21.05.2026 39p

  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.   See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 5 (The Therapist) 14.05.2026 49p

  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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 4 (The 4th Date Curse) 07.05.2026 49p

  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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 3 (Poison Ivy & The Algorithm) 30.04.2026 39p

  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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
• Casey: Date 2 (Trinket Tom) 23.04.2026 36p

  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.
• Casey: Date 1 (The Evangelical Ghoster) 16.04.2026 31p

  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 McGurrinIn 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.
• The Dating Debrief: Coming April 16th! 09.04.2026 1p

  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.