#20: She Asked Him To Rank Himself Against Her Exes
Mid-date, she pulls out her phone and casually scrolls to photos of two exes. No warning. No irony. Then comes the question: where would he rank himself compared to them? It’s delivered like a fun icebreaker, not an emotional landmine.

It’s excruciating. There’s no correct answer, no graceful exit, no way to participate without losing. The date quietly collapses under the weight of unresolved baggage. What should’ve been about getting to know each other turns into a pop quiz on relationships that already failed — and he didn’t even get the study guide.
