Matchmaking sounds like a favour until someone gets hurt, and Jen Kirsch has watched it go wrong from every angle. Friends turned into third parties, blind dates built on nothing more than a shared taste in music. When does connecting two people actually help, and when does it just create a mess.

She's been on exactly one blind date, set up through a hair salon connection that sounded perfect on paper and didn't survive reality. That shaped how she sees paid matchmaking services, the cost, and whether the price tag is doing more work than people think.

There's a version of matchmaking most people miss, recommending someone for a job you've never actually worked with them on. Jen also draws a line on how often you can ask friends to set you up before it starts working against you.

Topics: matchmaking, blind dates, dating apps, paid matchmakers, friendship boundaries

GUEST: Jen Kirsch | @‌jen_kirsch

Originally aired on 2026-09-03

Matchmaking sounds like a favour until someone gets hurt, and Jen Kirsch has watched it go wrong from every angle. Friends turned into third parties, blind dates built on nothing more than a shared taste in music. When does connecting two people actually help, and when does it just create a mess.
She's been on exactly one blind date, set up through a hair salon connection that sounded perfect on paper and didn't survive reality. That shaped how she sees paid matchmaking services, the cost, and whether the price tag is doing more work than people think.
There's a version of matchmaking most people miss, recommending someone for a job you've never actually worked with them on. Jen also draws a line on how often you can ask friends to set you up before it starts working against you.
Topics: matchmaking, blind dates, dating apps, paid matchmakers, friendship boundaries
GUEST: Jen Kirsch | @&zwnj;jen_kirsch
Originally aired on&nbsp;2026-09-03

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.