Dating coach Tony Tedesco flips the usual red flag conversation on its head, explaining why the way someone describes a past relationship tells you almost everything you need to know. Anyone tired of scanning profile pictures for clues will want a better filter, and this is one worth stealing.

Jen Kirsch adds her own list, from valuing therapy and self-awareness to why keeping small promises matters more than grand gestures, plus the exact kind of apology that actually rebuilds trust.

The two trade takes on spontaneity, comfortable silence, and why a friendship's value has less to do with how many years it has lasted and more to do with whether it is still active today.

Topics: dating green flags, emotional maturity, relationship reliability, apologizing well, comfortable silence

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

Originally aired on 2026-07-28

Dating coach Tony Tedesco flips the usual red flag conversation on its head, explaining why the way someone describes a past relationship tells you almost everything you need to know. Anyone tired of scanning profile pictures for clues will want a better filter, and this is one worth stealing.
Jen Kirsch adds her own list, from valuing therapy and self-awareness to why keeping small promises matters more than grand gestures, plus the exact kind of apology that actually rebuilds trust.
The two trade takes on spontaneity, comfortable silence, and why a friendship's value has less to do with how many years it has lasted and more to do with whether it is still active today.
Topics: dating green flags, emotional maturity, relationship reliability, apologizing well, comfortable silence
GUEST: Jen Kirsch | @&zwnj;jen_kirsch GUEST: Tony Tedesco | @&zwnj;tedescotony
Originally aired on&nbsp;2026-07-28

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.