The Dating Debrief

Casey: Date 6 (The Matchmaker)

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 [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 5 (The Therapist)

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 [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 4 (The 4th Date Curse)

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 [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 3 (Poison Ivy & The Algorithm)

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 [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 2 (Trinket Tom)

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 [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].