Relationship columnist Jen Kirsch and commentator Tony Tedesco join date night to unpack why the people closest to us have the most power to hurt us, and what that actually reveals about the patterns we carry into every relationship.

The disappointment you feel in love rarely has much to do with what just happened. Jen and Tony get into why our unspoken expectations set the stage for the arguments we think are about something else entirely, and why the things that bother us most about a partner tend to say more about us than about them.

When repeated conversations produce no change, that is not a communication problem. It is a signal. This conversation names what that signal means and what to do with it.

Topics: relationships and expectations, attachment, love and disappointment, emotional patterns, communication in relationships

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

Originally aired on 2026-06-17

Relationship columnist Jen Kirsch and commentator Tony Tedesco join date night to unpack why the people closest to us have the most power to hurt us, and what that actually reveals about the patterns we carry into every relationship.
The disappointment you feel in love rarely has much to do with what just happened. Jen and Tony get into why our unspoken expectations set the stage for the arguments we think are about something else entirely, and why the things that bother us most about a partner tend to say more about us than about them.
When repeated conversations produce no change, that is not a communication problem. It is a signal. This conversation names what that signal means and what to do with it.
Topics: relationships and expectations, attachment, love and disappointment, emotional patterns, communication in relationships
GUEST: Jen Kirsch | @&zwnj;jen_kirsch / Tony Tedesco | @&zwnj;tedescotony
Originally aired on&nbsp;2026-06-17

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.