The Dating Episode: Gen Z to Millennial to Boomer – Red Flags, Roster Reductions & Real Talk

On this week’s episode of Stall Talk, we’re diving deep into the perspectives of dating from different generations—from Gen Z to Millennial to Boomer. Cassandra’s dating roster has gotten significantly shorter (maybe even down to one 👀), and she’s sharing the highs, lows, and everything in between. Jenilee brings her signature humor and grounded wisdom, reminding us that no matter your age, navigating love is always a journey. Joining the conversation is celebrity fashion stylist and millennial Ivanna Fontana, who opens up about dating in your 30s. From red flags and dating app fatigue to the unique challenges of finding love in LA, Ivanna and Cassandra get real about vulnerability, feminine energy, and the pressure to “figure it all out.” And yes—there are a few dating horror stories you won't want to miss. For the recap, Jenilee comes back in with the Boomer perspective—sharing what it’s like to return to the dating scene and offering thoughtful insight on what it really means to want (or not want) someone in your life. This raw, relatable conversation is for every woman who's ever questioned being alone, being enough, or being ready. Because no matter where you are in life—love starts with knowing yourself.