The Dating Debrief

 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...

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-aw...

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 rea...

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 abou...

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 differen...

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 act...

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...

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 m...

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 un...

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 mus...

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 join...

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 conn...

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 wi...

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