Single men stereotypes have exactly two settings right now, and neither of them is accurate. You’re either a playboy or you’re an incel, and the middle ground, the guy who simply hasn’t found what he’s looking for and genuinely enjoys going to bed when he wants, doesn’t have a narrative yet. Women have two books on Jen’s desk romanticizing singlehood. Men have a Reddit thread where the married guys with kids get the most upvotes explaining how empty life would be without a family.

That Reddit thread is Tony’s example and it lands hard: the most popular comments weren’t from outsiders judging single men, they were from other men. Jen’s observation runs parallel, women went from spinster-coded books a decade ago to social media ownership of being single by choice, and men never got that transition. Shane’s building has elderly widows everyone says are living their best lives and one old man alone that everyone calls a shame.

The question left at the end of this one is worth sitting with: are you confidently navigating your relationship the way it is, or are you insulating yourself from the risk of losing one?

Topics: single men stereotypes, happy bachelor, living apart together, men singlehood stigma, dating by choice

GUEST: Tony Tedesco and Jen Kirsch

Originally aired on2026-02-27