See, I’m the same way. I’ll intentionally make myself look stupid—and it should be clear it’s a joke. But maybe you need the context of knowing the person to understand that? Because the understanding and volleying back of the repartee drops significantly on dating apps. Everything I mention on my profile is a joke, so…expect jokes when we match? I think people just assume the worst—particularly women on dating apps, most likely as a defense mechanism. I assume women have to go into every encounter with male strangers on the internet already on guard. So when anything out of the ordinary gets thrown their way, they’re just like, “…eh, I think it’s probably safer just to shut this down now before it gets weird.”

That’s what I tell myself anyway. Because I know I’m hilarious and it’s absolutely not that my jokes aren’t landing. They’re landing. Women are just intimidated by my wry wit.