Dating after 50 puts a question on the table that nobody talks about out loud: is this chemistry, or is this indigestion? Jen Kirsch and Tony Tedesco sat with that question, and the answer is more honest than most people expect.

What would it mean to realize the reason dating feels hard right now is not the other person? It is the life you built. The routine. The show you were watching when the text came in. Tony Tedesco calls it getting used to having someone in your life. Jen Kirsch calls it knowing what you will and will not put up with. Both are right, and both make those first few dates harder than they look from the outside.

The clock is not the enemy and neither is the comfort. What trips people up is not knowing the difference between inconvenience and incompatibility, and this conversation names that gap directly.

Topics: dating after 50, new relationship stress, dating anxiety, relationship routines, late life dating

GUEST: Tony Tedesco and Jen Kirsch

Originally aired on 2026-03-24

Dating after 50 puts a question on the table that nobody talks about out loud: is this chemistry, or is this indigestion? Jen Kirsch and Tony Tedesco sat with that question, and the answer is more honest than most people expect.
What would it mean to realize the reason dating feels hard right now is not the other person? It is the life you built. The routine. The show you were watching when the text came in. Tony Tedesco calls it getting used to having someone in your life. Jen Kirsch calls it knowing what you will and will not put up with. Both are right, and both make those first few dates harder than they look from the outside.
The clock is not the enemy and neither is the comfort. What trips people up is not knowing the difference between inconvenience and incompatibility, and this conversation names that gap directly.
Topics: dating after 50, new relationship stress, dating anxiety, relationship routines, late life dating
GUEST: Tony Tedesco and Jen Kirsch
Originally aired on&nbsp;2026-03-24

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.