Speed Dating Disasters, Self-Love Detours, and Why We Should Probably Just Start Our Own Matchmaking Service

Katie went speed dating. The men were older than advertised. One of them slipped her his number anyway — against the actual rules. And somehow, this became the perfect jumping-off point for everything. Michelle and Katie — two women in their 40s navigating the wildly weird world of midlife dating — are back for round two, and this episode goes deep. They talk about what it actually means to love yourself before you look for love from someone else (spoiler: it's not just a bumper sticker), how emotional self-regulation is the skill nobody taught us and everybody needs, and why building a secure attachment with yourself is the real foundation under every relationship you'll ever have. They also roast the apps. Extensively. With joy. And yes — by the end of this episode, they will have half-seriously proposed starting their own dating service. You'll understand why. In this episode: Katie's speed dating recap, including the men who were definitely not her age range Why rule-breaking romantic gestures aren't cute — they're just rule-breaking Learning to self-regulate before you expect a partner to do it for you Secure attachment as a personal practice, not just a relationship dynamic The app experience: what's broken, why it's broken, and what we'd do instead The business idea that might actually make sense If you're dating after divorce, re-entering the dating scene in your 40s or 50s, healing your attachment patterns, or just trying to figure out who you are before you find someone to be with — pull up a chair.