“Dating is about meeting the person you’ll spend your life with. It deserves preparation”

Shaul Kass was a catch. Every girl who dated him would tell you so. But none wanted to marry him. While Shaul had impeccable middos and was a great learner, he lacked the ability to be emotionally intimate.

OR

rather, he had lacked the ability. Over six months of hard work, Shaul had drilled down into his inner world, learning to identify his own feelings and to respond appropriately to the emotions of others. He was ready to date.

The shadchanim — who had been baffled and frustrated when one of the best boys on the market had been politely turning down their suggestions — were thrilled.

Hindy Danziger was the first girl Shaul met after his break. We prepped rigorously.

“Isn’t this excessive?” Shaul wondered aloud. “If she’s the right one, shouldn’t conversation flow naturally?”

“Not necessarily,” I replied. “People often plop into a date, figuring, hey, we’ll meet and take it from there. Would you go to a job interview with that approach? Dating is about meeting the person you’ll spend your life with. It deserves preparation.

“Let’s come up with a list of ideas that will not only impart information but also give her a window into your emotional world. It could be topics like going to yeshivah out of town, going to Eretz Yisrael, or trying to find a job. You want to share not only what happened but also how it felt.”