Kerri Pomarolli's dating life officially became a sitcom. One nine-hour first date, one incredibly thoughtful Christian dad, one accidental Instagram crush... and absolutely no clue what's happening next.
In this episode of We Might Get in Trouble for This, Kerri and Suze unpack the latest chapter in Kerri's Gen X dating adventures. There's the mysterious "Pirate" who planned an unforgettable first date but never asked for a second one. Then there's the thoughtful Christian guy who checks almost every box—but keeps texting without putting an actual date on the calendar. And somehow, an Instagram dating influencer unexpectedly enters the story too.
Along the way they talk about dating after 50, Christian dating, modern dating apps, mixed signals, intentional relationships, parenting while dating, attraction, boundaries, prayer, and why today's dating culture can feel like negotiating with the FBI.
It's funny, honest, awkward, relatable—and exactly what happens when two Gen X friends process dating in real time.
Have you ever liked someone who just... wouldn't make a move? Are people overthinking dating today?
Watch and tell us who you're rooting for: The Pirate, the Nice Christian Guy... or someone else entirely.
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