Wanting what you cannot have applies to more than diets and dream cars. Tony Tedesco and Jen Kirsch dig into why the person just out of reach so often becomes the one we cannot stop thinking about, and why that pull rarely has much to do with who they actually are.

They trace it back to a Psychology Today piece on why brief encounters and near-misses stick harder than real relationships ever do, and why the version of someone built entirely in your head is nearly always more romantic than the reality would have been. Kirsch explains why rom-com yearning has become such a cultural moment right now, and Tedesco admits exactly who still lives rent-free in his.

The conversation turns to what happens when you build a life you actually want first, rather than waiting for someone else to complete it. Then Shane puts both of them on the spot with one question neither sees coming.

Topics: wanting what you can’t have, dating psychology, the one that got away, yearning, relationships

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

Originally aired on2026-07-07