That in itself wasn’t such a big deal. It wasn’t a snowstorm, which could make driving difficult, and in any case, Yehuda was already there. The problem was that the rain came suddenly, one of those instant downpours where one second the sky is clear and the next second there’s a downpour. The kiruv event was caught by surprise, and everyone there got soaked.

Still, there really should have been no problem, since Yehuda had brought a change of clothes.

Except for his hat.

Yehuda called his mother. “My hat drowned in the rain,” he announced with his trademark humor. “I guess I need to buy a new one.”

His mother, aware that for Yehuda a new hat was going to run her around $300, didn’t love that idea. “Are you sure?” she said. “It’s still very new. Maybe the hat store could rehabilitate it somehow?”

“Could be,” Yehuda admitted grudgingly. “But that won’t help me now, I need a hat for my date in three hours.”

“Could you borrow one?”

“Ma! That’s like borrowing a sheitel!”

“Try to make it work,” his mother said.

Yehuda hung up in a huff at around 11 a.m.

Miriam texted me to let me know what had happened. Do you think we should tell the girl what happened so she’ll understand if he doesn’t look his best?

Then, before I could answer, she sent another message. Forget it. It’s 11:10 now. I’m leaving right away, I’ll bring Yehuda his other hat.

Wow! I replied.

Yehuda called me at 6 p.m., on his way home from his date, clearly drained. I’d never heard him sound like this. It had probably been a mistake to schedule a date after the kiruv event — he was exhausted, and the snafu with his hat had really rattled him.

“But wait!” I said, eager to hear about the happy ending. “Were you totally shocked when your mother showed up with your other hat? Was that amazing?”

“I didn’t wear it.”

“What?”

“I didn’t wear it,” Yehuda said bitterly. “She should have let me buy a new hat.”

“Yehuda,” I said, trying to keep calm and my voice even, “you realize that your mother dropped everything and drove two hours each way to bring you your hat so you would feel as comfortable as possible for your date?” A thought occurred to me. “Didn’t you want to wear the other hat?”

“I did,” Yehuda said, “but I refuse to let her think that she can get away with that.”

I was in territory I did not want to be in. There were obviously some very unhealthy dynamics going on here. I politely excused myself and hung up.

Then I called Dr. Freidland, a psychologist. “I feel like there are some serious control and manipulation issues playing out here,” I said. “Do I have to be concerned that these dynamics will transfer to the way he will interact with and treat his wife?”

Dr. Freidland explained that mother-son relationships could be extremely complex, but that didn’t necessarily mean that Yehuda would definitely mistreat his wife.

I wasn’t convinced. Could I continue setting Yehuda up? What would I tell people who asked me about him?

“Maybe,” I speculated, “his mother didn’t know how to fulfill Yehuda’s emotional needs, and Yehuda’s resentment toward her caused him to resent her generous gesture as well.”

Dr. Freidland chuckled. “That could be one explanation. Do you want to consider a career as a psychologist?”

I had to ask again. “Are you sure that this issue is not going to manifest in any way within a marriage?”

“If there’s open and healthy communication between him and his wife, things could be fine,” Dr. Freidland reiterated. “But he should get some help to work through his history with his mother.”

When I suggested that to Yehuda, he said he didn’t need any help, thank you very much. I told him he should think about it. He called me two days later to say he had spoken to his rebbi and asked if he felt he needed a psychologist.

Yehuda didn’t elaborate on what exactly he had told his rebbi, and I doubt he told him about the incident in which he spurned his mother’s generous assistance. Yehuda reported that his rebbi saw no reason for him to see anyone.

I never heard from Yehuda again; presumably his rebbi told him to stay far away from that “crazy shadchan.”

I wasn’t able to help him. But I’m sharing this story because maybe, somehow, it can help someone else.

to be continued…

Shani Leiman is a teacher, shadchan, and dating coach. She lives in Silver Spring, Maryland.

(Originally featured in Family First, Issue 713)