What happens when we carry old attachments into new relationships? Jen Kirsch and Tony Tedesco join to unpack the concept of “monkey barring” in dating, the fear of being alone, and how emotional attachments shape our choices. The conversation explores the role of self-awareness, when it’s healthy to step back from dating, and why letting go of the past is key to growth. They also share practical advice on solo travel, discovering connection in unexpected places, and embracing experiences that build resilience.

Guest: Jen Kirsch, Tony Tedesco

Originally aired on 2025-09-05

What happens when we carry old attachments into new relationships? Jen Kirsch and Tony Tedesco join to unpack the concept of &ldquo;monkey barring&rdquo; in dating, the fear of being alone, and how emotional attachments shape our choices. The conversation explores the role of self-awareness, when it&rsquo;s healthy to step back from dating, and why letting go of the past is key to growth. They also share practical advice on solo travel, discovering connection in unexpected places, and embracing experiences that build resilience.
Guest: Jen Kirsch, Tony Tedesco
Originally aired on&nbsp;2025-09-05

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.

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