Age Gap Relationships: Would You Date Someone a Decade Older Again?

If you've ever dated someone years apart from you in age, this one puts language to what that actually felt like, the parts that worked, and the moment it stopped. Tony Tedesco and Jen Kirsch share their own age gap relationships and the exact point where growing at different speeds became the reason things changed. Jen Kirsch talks about a decade-older relationship that felt like perfect timing until she kept growing past it, and why missing someone's cultural references matters more in dating than it seems. Tony Tedesco explains what it's like watching a partner get left behind once your own life accelerates, and why that isn't really about the number attached to someone's age. Both answer the question worth sitting with either way: would you do it again. Topics: age gap relationships, dating older, dating younger, relationship growth, dating advice GUEST: Tony Tedesco | @‌tedescotonyGUEST: Jen Kirsch | @‌jen_kirsch Originally aired on 2026-07-15