Then Yehudis added, “I have a date tomorrow. Can you help me?”

I tried to introduce Yehudis to a different mindset than I’d seen her display until now.

“When I was a kid,” I told her, “My father a”h would bring home guests for Shabbos. These were boys who were still on their way to discovering Yiddishkeit, and their clothes were as colorful and diverse as their backgrounds. But once they started talking, you could see their sincerity and intelligence. The conversations around the table reflected their essence.

“I learned never to just a book by its cover — you have to learn what’s inside to get the whole story. Can you try to keep that in mind when you meet someone new? Turn off the analytical, critical, judge-y voice, and instead be flexible and open to learning about who they really are.”

I tried to guide Yehudis to what a first date should be. “Imagine you’re in school and a new girl comes to your class. The first thing you do is try to find things you have in common to schmooze about.”

“I was never that kid who could go over to the new kid,” Yocheved objected.

“Right — when you were 14 you felt awkward and didn’t know what to say. But you’re 32 now. When you get introduced to a new coworker, how do you handle it?”

“I introduce myself, ask them where they’re from, make small talk.”

“Exactly. You’re making them feel comfortable and welcome. You’re not looking them up and down and thinking, ‘way too frumpy.’ Even if they are kind of frumpy. You’d ignore that and try to get to know them. Right?”

“I see what you mean,” Yehudis said.

“That warm, friendly Yehudis who greets a new coworker without judgment — that’s the Yehudis who should be going on a date with the new boy tomorrow night,” I said. “That’s what I mean when I talk about flexibility. Instead of thinking not my style, not my type, too nerdy, too brainy, too full of himself, too materialistic, act like he’s another guest at the Shabbos table. Just try to befriend him and get to know him a little.”

Yehudis called me about two weeks later. “I went out with him four times,” she told me. She sounded a little breathless. “I haven’t gone out with someone four times in years! Mrs. Leiman, you should have seen what he wore on the first date — an iridescent pink tie. And brown shoes with white soles! It was hideous. I would have said no right away. A guy like that is definitely not for me. But I remembered what you said, and I tried to be a ‘good hostess.’”

I was wowed at her ability to integrate what we’d talked about and her commitment to making real change.

“I’m not going out with him anymore,” she told me. “He wasn’t for me — for real. The difference is that I know why he wasn’t for me.”

This time, when Yehudis hung up, I didn’t have that heavy-hearted feeling. It felt more like hope.

The change in Yehudis’s attitude opened up many new possibilities for her. One of those possibilities was Dovi. Although he had been suggested for Yehudis at least twice a year since she was 20, she had consistently refused to consider him because his parents had been through a prolonged and messy divorce. But her new, flexible, and less judgmental attitude allowed her to get to know Dovi himself without evaluating him solely based on his family history.

It was hard work, but it was worth it. Three months after Yehudis’s younger sister got married, Yehudis and Dovi were engaged.

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

(Originally featured in Family First, Issue 748)