If you've ever dated someone years apart from you in age, this one puts language to what that actually felt like, the parts that worked, and the moment it stopped. Tony Tedesco and Jen Kirsch share their own age gap relationships and the exact point where growing at different speeds became the reason things changed.

Jen Kirsch talks about a decade-older relationship that felt like perfect timing until she kept growing past it, and why missing someone's cultural references matters more in dating than it seems. Tony Tedesco explains what it's like watching a partner get left behind once your own life accelerates, and why that isn't really about the number attached to someone's age.

Both answer the question worth sitting with either way: would you do it again.

Topics: age gap relationships, dating older, dating younger, relationship growth, dating advice

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

Originally aired on 2026-07-15

If you've ever dated someone years apart from you in age, this one puts language to what that actually felt like, the parts that worked, and the moment it stopped. Tony Tedesco and Jen Kirsch share their own age gap relationships and the exact point where growing at different speeds became the reason things changed.
Jen Kirsch talks about a decade-older relationship that felt like perfect timing until she kept growing past it, and why missing someone's cultural references matters more in dating than it seems. Tony Tedesco explains what it's like watching a partner get left behind once your own life accelerates, and why that isn't really about the number attached to someone's age.
Both answer the question worth sitting with either way: would you do it again.
Topics: age gap relationships, dating older, dating younger, relationship growth, dating advice
GUEST: Tony Tedesco | @&zwnj;tedescotony GUEST: Jen Kirsch | @&zwnj;jen_kirsch
Originally aired on&nbsp;2026-07-15

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.