Waiting for the perfect kallah was a recipe for disaster

I was 17 years old and playing a game of basketball with my high school’s team. Midway through the game, some of my teammates were standing on the court and waiting for the point guard to pass them the ball, when a member of the opposing team bolted in front of them, stole the ball, and proceeded to score a basket. Our team’s coach, Coach Mullen, suddenly called a timeout. When the players gathered around him, he flung his clipboard to the floor in exasperation.

“You can’t just wait for the ball to come to you!” he roared. “You have to go out there and get the ball!”

*****

Before entering shidduchim, I had been under the naive illusion that because there’s a shidduch crisis, girls would jump at the opportunity to go out with a nice, frum bochur like me, and I would have no shortage of dates. The way I understood it, if you’re a boy entering the parshah and you’re basically normal, in any sense of the word, then girls will be desperate to go out with you.

My experience in shidduchim utterly dispelled that misconception.

I had learned in right-leaning yeshivos, but I came from a decidedly non-yeshivish out-of-town community and had been raised by older, second-time-married parents who were not just baalei teshuvah, but out-of-the-box baalei teshuvah who never quite integrated into the frum community. (They named me Yoav, for instance — hardly a typical yeshivish name.) Well-meaning as they were, they didn’t quite get the nuances of frum living, and going into shidduchim I knew I would have to fend for myself.

In the yeshivos I had attended, college had been a dirty word, and throughout my late teen years, I was sure I’d spend the rest of my life in kollel. When I returned from learning in Eretz Yisrael, I associated with the long-term-learner crowd, and did not think too deeply into plans for the future — until I went out on my first date, when I was 23.

I wore a hat and jacket throughout the entire date, all the while thinking to myself, I’m not a hat-and-jacket guy. And when the girl talked about moving to Eretz Yisrael and learning in kollel long-term, I felt uneasy. That’s not me, I thought.

But who was I?

After that first date, I decided to take a break from shidduchim while I figured myself out.

I was trying to throw myself into my learning at yeshivah, but the more I thought about who I was and where I was going, the more I realized that I was just thrashing about in the beis midrash, pretending to be someone I wasn’t. Torah learning was important to me, but I couldn’t do it all day. It was time for a change.

I left yeshivah and began looking for a respectable job while trying to maintain a consistent learning schedule. The job search was really challenging, and being out of yeshivah made it difficult to learn a solid amount every day. After several months, however, I finally landed a decent office job and found a great chavrusa.

Well, at least now I wasn’t living a charade. About a year after my first date, I officially reentered shidduchim, thinking that now I was better positioned to meet the type of girl who was right for me.

Boy, was I wrong.