Affordable dating can still feel like being someone’s priority. Tony Tedesco and Jen Kirsch offer ways to put thought into a date without turning getting to know someone into an expensive production.
Wanting to be courted is one thing. Leaving room for someone else to make the plan is another. Jen recognises a habit that gets in the way of the romance she wants, and her idea of meaningful effort has little to do with a fancy reservation.
Then the bill arrives. Both have a preference about who pays, but Tony’s expectations don’t end with covering dinner. Add the time spent travelling and the temptation to date because you’re lonely, and the price of an evening becomes a more personal calculation.
Topics: affordable dating, romantic effort, date planning, dating expectations, who pays
GUEST: Tony Tedesco | @tedescotony
GUEST: Jen Kirsch | @jen_kirsch
Originally aired on 2026-10-26



