Dating what to say

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.

I read dozens of studies about love, how people connect and why they do or don’t stay together.

The first woman he clicked on was very beautiful, with a witty profile page, a good job and lots of shared interests, including a love of sports.

After looking the page over for a minute or so, Derek said, “Well, she looks O. I’m just gonna keep looking for a while.” I asked what was wrong, and he replied, “She likes the Red Sox.” I was completely shocked. Imagine the Derek of 20 years ago, finding out that this beautiful, charming woman was a real possibility for a date.

But dealing with this new digital romantic world can be a lot of work.

Answering messages, filtering profiles—it’s not always fun.

As of this writing, 38% of Americans who describe themselves as “single and looking” have used an online-­dating site.

It’s not just my ­generation—boomers are as likely as college kids to give online dating a whirl.

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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.

10 in., has brown hair, lives in Brooklyn, is a member of the Baha’i faith and loves the music of Naughty by Nature.

Before online dating, this would have been a fruitless quest, but now, at any time of the day, no matter where you are, you are just a few screens away from sending a message to your very specific dream man. Throughout all our interviews—and in research on the subject—this is a consistent finding: in online dating, women get a ton more attention than men.

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.

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