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June 2, 2026

ICYMI – Dating: When Agreeing to Disagree Stops Working

Swiping past someone because their profile opens with a political slogan is now a dating strategy — and it might be the rational one.

Tony Tedesco does it. Not because he disagrees, but because leading with that energy is a preview of every conversation to come. He’s seen what happens when political differences stop being a quirk and start being a values gap.

Jen Kirsch has a different approach: draw the line early, keep it light if you can, and know that nobody wins those arguments anyway. She learned that from years writing a column on reading the room — and from one car ride with her father that went sideways the moment someone mentioned the news.

Topics: politics and dating, dating app red flags, political identity in relationships, relationship conflict, values alignment

GUEST: Jen Kirsch, Tony Tedesco

Originally aired on2026-06-01