The Midlife Mess

Midlife Dating: The Good, the Bad, and the Ugly

Lara Thompson Season 1 Episode 3

In this deeply honest and often hilarious episode, Lara opens up about what it’s really like to date in midlife—for the first time. After two marriages and a late start in the dating world, she shares the lessons she’s learned over the past five years navigating online dating, shifting expectations, and her own evolving sense of self.

Lara walks listeners through the good (clarity, honesty, emotional depth, and unexpected confidence boosts), the bad (misaligned life stages, Peter Pan syndrome, online dating fatigue, and wildly different relationship goals), and the ugly—including ghosting, cheaters, ethically non-monogamous surprises, and why Facebook groups like Are We Dating the Same Guy? even exist.

Along the way, she reflects on body image, trauma-informed attraction, sex “rules,” trusting your gut, and why women today are no longer willing to be expendable in relationships. The episode wraps with hard-earned dating wisdom, unapologetic expectations, and a blunt—but loving—PSA for men in the online dating pool.

Raw, funny, reflective, and validating, this episode sets the tone for Midlife Mess: real conversations, no pretending, and learning how to be your best mess—together.