“Absolutely.” I looked directly at her. “I believe that everyone deserves a second date, with one exception — a red flag. And I mean a real red flag, like if your date used inappropriate language, blamed you for something that went wrong, or made fun of his parents or rebbeim. There could be others. If they happen, you’ll know something is ‘off.’ And if you’re worried you won’t know, you could always discuss your dates with someone who understands relationships.”

“But sometimes you go out with a boy and you just can tell this isn’t the right personality for you. Why bother with a second date?” Shira argued.

“Shira, so many girls and boys have resisted my encouragement to go out a second time, all with the same argument — they ‘know’ 100 percent that this person is not for them. But I always try to convince them to give it a second try.”

“So, they go out one more time to make you happy and then say no. How does that help?”

“They go out one more time, and then often they go out again after that. And sometimes again and again. And sometimes they get married. Because they discover a very different person on the second date. It isn’t really possible to know a person ‘100 percent’ after just one date.”

Shira mulled this over.

“Shira, when you go out, you’re eager and excited to meet someone. A new person, a new challenge, a new perspective. People are interesting to you. You’re in your element.”

“Totally,” Shira said, her trademark smile lighting up her face.

“But what if you’re a more introverted girl and it takes you time to warm up and be yourself? Or maybe you’re not at all introverted, but you’re more reserved with a boy? A first date can be pretty uncomfortable.”

Shira nodded. “I hear that. I have six brothers, and I’m used to boys. But I know some of my friends find dating very awkward.”

I told Shira about Yoni. When I’d recently set him up with Tzipora, he’d said no after their first date. Actually, he didn’t only say “no,” he said “no way.” Although Tzipora had grown up in Lakewood and gone through the regular yeshivish school system, her family background was Sephardic, and he said he could never get used to her “look.” When I asked him how the conversation went, he said it flowed well, but he was still very uncomfortable.

“I know you always tell me to go for a second date,” he said, “and if you insist, I will. But I’m telling you she’s not for me. No way.”

“You know what, Yoni,” I said. “Forget the second date.”

“What?”

“I want you to skip to the third date. Talk to her about hashkafah. I’ll make sure she’s okay with that. I want you to get to know her in a different way. At least if you say no, you’ll know what you’re saying no to.”

Yoni and Tziporah’s second-slash-third date lasted six hours. Yoni called me the next day and filled me in, in great detail, on everything they had talked about. As he was talking, I was waiting.

But it never came.

The no.

“I don’t know what got into me after the first date,” he admitted sheepishly. “She’s really pretty and has such incredible depth and passion for Yiddishkeit. I only ended the date because it was already way too long. The time flew by.”

Shira looked at me expectantly. “Did they get engaged?”

“They sure did.”

“Wow.”

“It happens all the time.”

Shira called me two months later.

“Okay,” she started. “I went out with my best friend’s husband’s chavrusa. You know those types of shidduchim? Where they’re soooo positive we’re perfect for each other? I had my doubts, but okay, I went out with him. And I really want to say no! He’s way too yeshivish for me!”

“Shira, you know my rule.”

“I knew he was going to be too yeshivish for me. I should never have gone out with him. He comes from a very yeshivish family, but they kept saying he’s not like his family. But he is! You should have heard him talking! I can’t. I know my type and this isn’t it.”

“Shira, I know this doesn’t make sense to you, but you have to trust me. Please go out again.”

“Seriously? Why?”

“Because maybe he’s not really like that. Maybe he was just nervous. Maybe a hundred things. You really can’t know yet.”

“Fine,” Shira grumbled. “I’ll do it for you.”

Actually it’s for you, I thought, but I didn’t say anything.

Shira called me a week later.

“So you went out a second time?”

“No,” she said. “I went out a second time and a third time and I’m going out with him again on Wednesday.”

Now it was my turn to say, “Wow.”

“He was totally different,” she said honestly. “You were right. It was like dating two different boys. We had a great time on the second date. He really isn’t as yeshivish as I thought he was. Maybe he was just nervous that first time.”

When they got engaged, Shira introduced me to her mother as “the second shadchan.” “Because I really wouldn’t be here if not for what you told me,” she told me seriously.

Then she leaned forward, winked, and whispered, “I didn’t need to look at my top-ten list even once.”

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

(Originally featured in Family First, Issue 743)