He would start out playing clueless yeshivishe yungerman, and if the situation called for it, he would let it slip that he got it, he’d been around the block, too

Back in Yerushalayim, Heshy had been one of many yungeleit who tried to work with American bochurim, but his approach was different from the rest.

The other ones planted themselves in yeshivos and the shuls in which boys learned, hoping desperately that a bochur would ask them a question so that they could engage them in conversation. But Heshy thought that the boys saw through that, and there was no reason to play games.

Instead, he used to go to the new cholent place behind the Meah Shearim shuk late on Thursday night and find himself an empty chair among the bochurim. They never minded when he joined: if anything, it added to their fun.

He would start out playing clueless yeshivishe yungerman, and if the situation called for it, he would let it slip that he got it, he’d been around the block, too.

In every group, he found a couple of boys who took to him, usually not the ones with obvious challenges, more likely the clean-cut ones from the wealthy homes. They needed it the most — they were stuck on a conveyor belt that they had no hope of climbing off of, and Heshy’s originality and color always attracted them.

Heshy didn’t think there was a reason to beat around the bush. The whole plan — invite them for a Shabbos meal, hope they linger after bentshing for a l’chayim, daven that they open up and share their life story, then follow up during the week and make sure that they didn’t suddenly start avoiding you because they felt awkward about how much they had shared — was a waste of time.