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Whether it’s where I’m eating, where I’m traveling or, God forbid, something I’m buying, like a lot of people in my generation—those in their 20s and 30s—I feel compelled to do a ton of research to make sure I’m getting every option and then making the best choice.

I quizzed the crowds at my stand-up comedy shows about their own love lives.People even let me into the private world of their phones to read their romantic texts aloud onstage.What I’m about to say is going to sound very mean, but Derek is a pretty boring guy.Medium height, thinning brown hair, nicely dressed and personable, but not immediately magnetic or charming.Even a guy at the highest end of attractiveness barely receives the number of messages almost all women get.

But that doesn’t mean that men end up standing alone in the corner of the online bar. Take Derek, a regular user of Ok Cupid who lives in New York City.

The first girl, he said, was “a little too tall,” and the second girl was “a little too short.” Then he met my mom. Let’s look at how I do things, maybe with a slightly less important decision, like the time I had to pick where to eat dinner in Seattle when I was on tour last year.

He quickly deduced that she was the appropriate height (finally! First I texted four friends who travel and eat out a lot and whose judgment I trust. Finally I made my selection: Il Corvo, an Italian place that sounded amazing. (It only served lunch.) At that point I had run out of time because I had a show to do, so I ended up making a peanut-butter-and-banana sandwich on the bus.

If she were at a bar and smiled at him, Derek of 1993 would have melted.

He wouldn’t have walked up and said, “Oh, wait, you like the Red Sox?! ” before putting his hand in her face and turning away.

The question nagged at me—not least because of my own experiences watching promising relationships peter out over text message—so I set out on a mission.