The Dating Debrief

Casey: Bonus Episode (Casey Returns)

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

Casey: Date 14 (The Psychic)

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

Casey: Date 13 (The Johnny Depp Wannabe)

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

Casey: Date 12 (Extra Credit with Teacher Trish)

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

Casey: Date 11 (The Cowboy Returns)

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