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.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.

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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.

I checked the website Eater for its Heat Map, which includes new, tasty restaurants in the city. The stunning fact remained: it was quicker for my dad to find a wife than it is for me to decide where to eat dinner.

This kind of rigor goes into a lot of my decisionmaking.

Throw in the fact that people now get married later in life than ever before, turning their early 20s into a relentless hunt for more romantic options than previous generations could have ever imagined, and you have a recipe for romance gone haywire.

In the course of our research, I also discovered something surprising: the winding road from the classified section of yore to Tinder has taken an unexpected turn.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.But dealing with this new digital romantic world can be a lot of work.Answering messages, filtering profiles—it’s not always fun.But Derek of 2013 simply clicked an X on a web-browser tab and deleted her without thinking twice.