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 on2026-09-03
