The “look” he was attracted to didn’t quite align with the hashkafos he was looking for

Shani Leiman with Zivia Reischer

Ari had everything going for him. He was tall and good-looking, with a ready smile, and carried himself with an easy grace. Wherever he went, people were naturally attracted to his easygoing personality and can-do attitude.

He’d been raised in a Modern Orthodox community, but had gradually grown more to the “right.” By the time he had graduated high school, he was deeply passionate about Yiddishkeit, and followed his more yeshivish friends to the Mir and then to Lakewood.

He’d started dating at 23, with an eye to long-term learning. There was no reason to think it would be hard for him to find the right one, but here he was, 27, single, and very frustrated.

“Basically,” he said, “every single girl says no after the fifth date.”

I’d worked with cases that always got a no after just one date, or always got a no after the third date. I was familiar with those patterns. But to always get a no after the fifth date? What was behind that?

“It’s like I have horns or something that only become visible on the fifth date,” Ari continued. “We go out once, twice, three, four times, everything is great. Then bam, fifth date, it’s over.”

“Tell me about the kind of girls you’re dating,” I said.

So he did — about their backgrounds, families, careers, hopes for the future. He seemed to be dating girls who were pretty much aligned with the milieu in which he’d placed himself. So that wasn’t the issue.

“What about looks?” I asked him.

“Never a problem,” he said confidently.

“And when you’re dating, do you discuss more serious topics? Do you check whether your hashkafos match?”

“Sure,” he said, “usually around the third or fourth date or so.”

When Ari named a few of the girls he had dated, something clicked.