Dating your ex sounds easier than starting over. Your phone lights up. It's them. Three years later, and suddenly they're back in your messages. The shared history. The inside jokes. The way they already know your family. It feels like skipping ahead to the comfortable part.

Jen Kirsch: "Just because something feels electric doesn't mean it's meant to be." Tony Tedesco admits he learned problems don't go away. Jen documents relationship issues through journaling specifically because chemistry makes you forget past hurts. Tony's realization: it was the hiking he liked, not necessarily the person. The phrase "it wasn't that bad" gets challenged. When was the last time that standard worked for anything? Both point to triggers that resurface, patterns you thought you'd outgrown.

Discover why familiarity feels like convenience but lands closer to comfort. Learn what Jen means by expectations that come with shared history. Understand why Tony suggests verifying growth takes time, not assumptions. Consider solo dating as the alternative nobody talks about.

GUEST: Tony Tedesco, Jen Kirsch

Originally aired on 2026-01-23

Dating your ex sounds easier than starting over. Your phone lights up. It's them. Three years later, and suddenly they're back in your messages. The shared history. The inside jokes. The way they already know your family. It feels like skipping ahead to the comfortable part.
Jen Kirsch: "Just because something feels electric doesn't mean it's meant to be." Tony Tedesco admits he learned problems don't go away. Jen documents relationship issues through journaling specifically because chemistry makes you forget past hurts. Tony's realization: it was the hiking he liked, not necessarily the person. The phrase "it wasn't that bad" gets challenged. When was the last time that standard worked for anything? Both point to triggers that resurface, patterns you thought you'd outgrown.
Discover why familiarity feels like convenience but lands closer to comfort. Learn what Jen means by expectations that come with shared history. Understand why Tony suggests verifying growth takes time, not assumptions. Consider solo dating as the alternative nobody talks about.
GUEST: Tony Tedesco, Jen Kirsch
Originally aired on&nbsp;2026-01-23

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.