Dating your ex sounds easier than starting over. Your phone lights up. It’s them. Three years later, and suddenly they’re back in your messages. The shared history. The inside jokes. The way they already know your family. It feels like skipping ahead to the comfortable part.

Jen Kirsch: “Just because something feels electric doesn’t mean it’s meant to be.” Tony Tedesco admits he learned problems don’t go away. Jen documents relationship issues through journaling specifically because chemistry makes you forget past hurts. Tony’s realization: it was the hiking he liked, not necessarily the person. The phrase “it wasn’t that bad” gets challenged. When was the last time that standard worked for anything? Both point to triggers that resurface, patterns you thought you’d outgrown.

Discover why familiarity feels like convenience but lands closer to comfort. Learn what Jen means by expectations that come with shared history. Understand why Tony suggests verifying growth takes time, not assumptions. Consider solo dating as the alternative nobody talks about.

GUEST: Tony Tedesco, Jen Kirsch

Originally aired on2026-01-23