JDate Lessons

After breaking up with the last Irish Catholic in a long line of Catholic boyfriends, I decided it was time to try something new.

It wasn’t religion that broke us up, although fighting about whether to get a Christmas tree didn’t help. What I knew was this: All the guys I’d been picking were wrong for me, and it was time to try a new dating strategy. Jews were new. In spite of being raised Jewish, I had only dated one member of my tribe. Maybe I was missing out. Maybe it’d be nice if I didn’t have to explain to a guy what Passover was.

Ten. That’s the number of guys I’d decided to go out with after signing up with JDate; 10 seemed like enough that I could say, "Yeah, I’ve dated Jewish guys before. Nothing ever clicked."

I also took some time to think through what traits for a guy were nonnegotiable to me. I settled on the following: He had to be thoughtful, playful, smart and creative. And it wouldn’t hurt if he were the kind of guy who’d sit through a chick flick with me every once in a while.

What was challenging was staying true to my nonnegotiable list. It was one of those good-for-you rules in theory, but not so easy in practice. For example, when I met David, a sharply dressed entrepreneur, I was taken immediately with his intelligence and spontaneity. He was also confident and had a knack for telling wild stories. What he didn’t have from my list was "thoughtful." This was clear after I began telling him about my family over dinner and his eyes began drifting around the room. (No, he was not just looking for our waiter.)

Before I came up with "The List," I probably would have gone out with David at least a few more times, enjoying his tales of adventure and his cobalt blue eyes. I would have told myself it was just "until the next guy came along." But I had promised myself I would stick to my new strategy. "Thoughtful." It was a nonnegotiable. David had to go. For a few minutes it was depressing; I’d never even gotten to smooch him. But once I reminded myself that this was about respecting myself enough to demand thoughtfulness in a guy, it felt kind of good. I deserved thoughtfulness. I ended it with David.

Another challenge popped up when I met Rob (not his real name). On paper, Rob had every quality on the list. He even had an excess of thoughtfulness, baking me a batch of chocolate chip cookies for a picnic date we’d planned and remembering small details I’d said in passing. He was warm and easygoing, and there was nothing "wrong" with him. The problem was there were no sparks for me.

I tried to force it, telling myself, "Wake up! He’s it." I even tried to convince myself the chemistry would kick in at some point, soft and surprising. It had to. But as it turns out, you just can’t force chemistry. You can’t make yourself look at someone and fantasize about a lifetime of Sunday breakfasts, lounging in pajamas and fighting for the Arts & Leisure section. I knew I had to part ways with Rob, No. 10 on the list of JDate men.

I decided to hang it up for a while. I needed a breather. I was starting to lose faith that my "one" even existed. And so when I got an e-mail from Ezra, guy No. 11, I said no. Sure, his e-mail was witty and his profile listed many of the qualities I was looking for. But it was time to stop. So I explained that I was just getting out of a relationship (which was true; I still had the dirty job to do of breaking up with Rob), but thanks anyway.

A few days later, I got another e-mail from Ezra. He didn’t ask me to give him a chance. He didn’t tell me I was making a big mistake or send me a list of his best traits. He sent his rendition of a food review column written by a high school stoner, riffing on a joke I’d made. It caught me off guard and cracked me up. I was going to delete it, but something stopped me. I wrote back that I’d like to get coffee if he was still open to it. He agreed.

Our coffee date lasted five hours. He created things for a living (he taught 3-D animation); he made me laugh; he was open and generous and he asked a lot of questions. It took a while for Judaism to come up, but it did and we had a lot in common with our religious beliefs. As for the chemistry? Rock solid.

In two weeks, Ezra and I are getting married. He is not perfect. He snores, he researches things obsessively on the Internet and his stories go off on unwieldy tangents. But I adore him. I am happy that I chose to aim so high. It’s true that if you’re too picky, you’ll lock yourself out of great people and experiences. Plenty of people will throw that sentiment in your face. But it’s good to have "must have" items on your list. They keep you on the track of finding what you want and focused on what you deserve.

I also think it’s important that Ezra was No. 11. The message I take is that you’ve got to be open in life. When it comes to dating, you can make all the rules in the world for yourself and try to regulate the process to the hilt. It feels good to take control of something that opens you to up to vulnerability and rejection. But the bottom line is, you’ve got to keep your mind and your heart open. Sometime No. 11 is the guy you end up sitting at the kitchen table with and fighting with for the Arts & Leisure section.

Michelle Silver is the editorial director of