“Just keep davening,” I said finally. “The right one at the right time.”

When Leah turned 24 her mother called me.

“Should we change what we’re looking for in a boy?”

“What do you mean?”

“Well, Leah’s been dating the same type of boy since she was 20. Maybe we need to widen the parameters a little? Should we be open to different types of boys, or boys from backgrounds we might not have considered until now?”

After some discussion, Leah decided she’d be open to dating boys who were currently learning, planned to work one day, but didn’t necessarily have a professional plan.

So, I set her up with Shaya — 25 years old, learning in Lakewood, planning to learn, with vague ideas about going into business one day, or maybe real estate. Leah went out with Shaya a few times, and although it didn’t work out, she reported to me that this “type” also seemed on target.

Leah kept herself busy. A few months later, she called to tell me that she and two friends were arranging shiurim geared toward single girls. Each week another speaker would address a different aspect of shidduchim, offering a Torah hashkafah and chizuk to the single girls in the community. I thought it was a wonderful idea.

Leah checked in frequently to see if I had any new ideas for her, and I loved getting updates on her new venture. She got to know many girls through this project. During one conversation, I had a sudden urge to tell her about a relative of mine who had just started dating.

“Maybe you know a girl for him?” I said to Leah. “He’s a great guy. He’s 23, he’s the type that when he’s there, you’ll know it from down the block — he has no compunctions about singing or whistling while walking down the street. He has a heart of gold and is incredibly generous, with a great sense of humor. His simchas hachayim is infectious, and just being around him puts you in a good mood. Kids love him, and he has the ability to get through to difficult kids who nobody else can reach. He plans to stay in learning for a few more years. After that he doesn’t have plans — maybe he’ll work with kids-at-risk or something. He has time to figure it out. Keep your eyes open, let me know if you meet a girl for him.”

When Leah spoke to her parents that night, she mentioned our conversation. “Do you know anyone for him?” she asked.

“Why not for you?” her father wanted to know. “He sounds wonderful!”

“Oh, but… if Mrs. Leiman thought it was for me, she would have just said so.”

“Ask her,” her father said.

“It’s so awkward!”

“So she’ll say it’s not the type, what do you have to lose?”

I’m totally putting myself out there, Leah texted me, but I was thinking about the boy you described. Do you think he would be shayach for me?

Then she immediately sent another text: I can’t believe I just sent that to you!

And a minute later: I hope I didn’t put you on the spot!

I called Leah. “I’ll tell you the truth, I didn’t ask if you’d be interested in him because his ‘plan’ isn’t quite what you’ve been looking for. I figured on the off-chance you’d be interested, you’d say so.”

I knew both sides well enough that the information gathering process went quickly. Less than a week later, Leah and Naftali were on their first date.

Which was followed by their second date, then third, fourth, fifth…

Their dating went pretty smoothly, though there were some funny incidents that happened along the way. Leah seemed to be able to handle Naftali’s very big personality and was humored by it.

Unfortunately, on their 16th date they got into a car accident. Baruch Hashem, it was pretty minor — they were in a parking lot and a minivan backed into them. Naftali jumped out of the car and ran around to open Leah’s door. “Are you okay?”

She was fine. Naftali turned to the minivan to make sure the driver was also okay. It was a young yeshivah guy, and he was profusely apologetic.

“No worries, my car seems fine,” Naftali assured him. “How’s your car?”

They examined both cars, and neither one seemed damaged. “Just make sure your trunk still works,” Naftali suggested.

He opened the trunk, and out flew an enormous bunch of balloons and an explosion of confetti. Stretched across the inside of the trunk was a giant sign: “LEAH, WILL YOU MARRY ME?” There was an oversized marker conveniently taped near the checkbox marked “Yes.”

Laughing, Leah circled the yes. As she leaned forward, she caught sight of the huge bouquet of roses resting in the trunk. They were officially engaged.

Ultimately, what had enabled Leah to meet her husband was her flexibility and open-mindedness —  Naftali was almost a year younger than her and not exactly what she was initially looking for.

Naftali thanked his friend for his part in their proposal. Then the glowing chassan and kallah headed to Naftali’s parents’ house. I was there already, waiting for them… Naftali, my son, and Leah, my very special daughter-in-law.

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

(Originally featured in Family First, Issue 752)