Leisure guilt is the reason you cancel plans and then spend the whole weekend feeling like you ruined something. Jen Kirsch and Tony Tedesco dig into why saying no to a date because you’d rather do nothing might actually be the healthier move, not the red flag it feels like.

The conversation gets into where the guilt actually comes from, the fear that skipping a date now means missing the version of yourself someone would have liked better. There’s a real question buried in there: what if the tired, worn out version of you is exactly who someone is looking for, not a performance you owe anyone.

Where they land isn’t guilt-free forever, it’s honesty instead of disappearing. Say what you actually want before the date instead of after, and let the other person decide if they’re in.

Topics: leisure guilt, dating apps, self-care, honesty in dating, guilt-free weekends

GUEST: Jen Kirsch | @‌jen_kirsch
GUEST: Tony Tedesco | @‌tedescotony

Originally aired on2026-07-21