Yehoshua, or Josh as his friends called him, was 27. His father was the longtime rav of the community shul, but Josh didn’t buy into the system. He saw himself as a square peg in a round hole, or maybe a triangle or a parallelogram. He dressed in a T-shirt and jeans, and, when the occasion demanded it, dress pants and a button-down shirt — any color but white.

He wasn’t too happy to deal with a shadchan, but I managed to convince him that I wasn’t the stereotypical intimidating and aggressive matchmaker, and he agreed to give it a shot.

When you talk to people in the language they’re used to and comfortable with, it helps them feel understood. When I talked to Josh and Judy individually before they met, I made sure they knew that I had a clear understanding of their dating styles and history. But I insisted on one thing: They could have fun, hang out, party, whatever, but they had to date with focus. Every date had to help them get to know each other better. For example, on one date, the focus could be for Josh to learn about Judy’s relationships with her family, and Josh would be similarly forthcoming with that information.

“I’ll check in with you to help you maintain that focus,” I told them, “so you don’t date for three months and then discover that you’re having fun but don’t really know much about each other.”

Judy and Josh were pleasantly surprised by the success of this system. “This focused approach is a game changer,” Judy admitted. They both understood the need for goals and progress.

After several weeks, Judy’s father called me. He was overwhelmed with emotion when I explained how I was guiding his daughter. “You’re doing what Yehudis’s mother would’ve wanted,” he said. “I can’t thank you enough. I’m so worried about her, but I’m powerless to help. Even though I don’t always understand why she does what she does, she’s still my daughter and I care about her very much.”

“I’ll do whatever I can,” I promised him. “Let’s give them space. Let them figure this out. Everything needs siyata d’Shmaya. I’ll keep you posted.”

I had a similar conversation with Josh’s parents. Like Judy’s father, they were also trying to be understanding of the lifestyle choices their son had made. Their concern and genuine interest in him were obvious, but they didn’t really get him. It was painful for them to accept that their son had rejected their lifestyle.

Judy and Josh got married — two beautiful people who had each chosen their own way. I had a lot of hope for their future.

They had each told me, separately, that despite everything they’d been through in their lives, despite the struggles they had faced, they still believed strongly that Hashem runs the world and that He had always been there for them.

And nothing could prove it to them more than the “accidental” meeting with the shadchan at the grocery store.

(Originally featured in Family First, Issue 705)