Leisure guilt is the reason you cancel plans and then spend the whole weekend feeling like you ruined something. Jen Kirsch and Tony Tedesco dig into why saying no to a date because you'd rather do nothing might actually be the healthier move, not the red flag it feels like.

The conversation gets into where the guilt actually comes from, the fear that skipping a date now means missing the version of yourself someone would have liked better. There's a real question buried in there: what if the tired, worn out version of you is exactly who someone is looking for, not a performance you owe anyone.

Where they land isn't guilt-free forever, it's honesty instead of disappearing. Say what you actually want before the date instead of after, and let the other person decide if they're in.

Topics: leisure guilt, dating apps, self-care, honesty in dating, guilt-free weekends

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

Originally aired on 2026-07-21

Leisure guilt is the reason you cancel plans and then spend the whole weekend feeling like you ruined something. Jen Kirsch and Tony Tedesco dig into why saying no to a date because you'd rather do nothing might actually be the healthier move, not the red flag it feels like.
The conversation gets into where the guilt actually comes from, the fear that skipping a date now means missing the version of yourself someone would have liked better. There's a real question buried in there: what if the tired, worn out version of you is exactly who someone is looking for, not a performance you owe anyone.
Where they land isn't guilt-free forever, it's honesty instead of disappearing. Say what you actually want before the date instead of after, and let the other person decide if they're in.
Topics: leisure guilt, dating apps, self-care, honesty in dating, guilt-free weekends
GUEST: Jen Kirsch | @&zwnj;jen_kirsch GUEST: Tony Tedesco | @&zwnj;tedescotony
Originally aired on&nbsp;2026-07-21

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.