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 on 2026-07-07

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 | @&zwnj;tedescotony GUEST: Jen Kirsch | @&zwnj;jen_kirsch
Originally aired on&nbsp;2026-07-07

Shane Hewitt & The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world—always with curiosity, compassion, and a sharp edge.

From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane’s signature style—thoughtful, fearless, and refreshingly real.

If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt &amp; The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world&mdash;always with curiosity, compassion, and a sharp edge.
From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane&rsquo;s signature style&mdash;thoughtful, fearless, and refreshingly real.
If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt and The Nightshift

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.