“And now, I actually know that myself,” Shaul said with a laugh.

I recommended sharing interesting books he’d read, bringing in a cartoon that caught his fancy, raising a topic he’d discussed with a friend and asking his date’s opinion. I also recommended playing dating games. Many couples have no problem having deep conversations but can’t always find a natural way to start them. Dating games give them a smooth, enjoyable way to bring up stickier topics.

“Perfect Matches” is a daters’ favorite. I also recommend “Deeper Conversations” and “Couple Reconnect,” two card packs you can get from Amazon.

Shaul and Hindy quickly discovered hashkafic differences and they ended things after three dates. Still, Shaul considered it a win because previously, it would have taken him twice as long to reach that realization.

Next, he met with Aliza Sher. Aliza ultimately said no, but she told the shadchan that, “It was amazing to meet with a guy who’s self-aware and a good listener.” So Shaul chalked that up as another win.

Then, he approached his favorite shadchan about Riki Margolis. “Many girls said no to me,” Shaul told me, “But she’s the one I keep thinking about. She’s solid and warm and so committed to her Yiddishkeit, and I think we can build something beautiful together. She said she couldn’t connect with me, but maybe now things will be different….”

It took a lot of persuasion to get Riki to try again, but finally a date was set.

We decided that it would best to go for full transparency and bring Riki on board at an early stage.

On their second date, Shaul shared his struggles with Riki.

“My family is amazing, but we’re not big on sharing emotions,” he told her candidly. “As you know too well, I had a hard time connecting emotionally. I’ve been working with a dating coach, and if you’d be up for it, I’d so appreciate if you’d speak to her.”

Riki was surprised, yet also impressed. She called me two nights later.

“Hi, I’m dating Shaul. And, um, he asked me to call you… which is kinda weird, but I was also really sad when things didn’t work last time, and if this can make a difference, I’m in.”

“You’re a smart woman,” I told her warmly. “Shaul will be a caring, devoted husband and father. He’s going to need a little help learning the ropes of how to connect with a woman, but he’s open and very willing to learn.

“I know some of these techniques may feel artificial and awkward at first, but pretty soon, it will become second nature, and in the long run, you’ll gain so much.”

The first thing I taught them both was the idea of hitting pause. When dating, there’s a lot of pressure because we know that every move and comment is being judged. When we request a pause, we’re asking for a shift in roles. We move from “guy and girl on a date” to “friend asking friend for advice.”

“Here’s how it would work,” I told Shaul. “Imagine Riki tells you something painful and you’re at a loss for what to say next. You’d say, ‘Can we pause the date for a moment?’

“Once Riki agrees, you can tell her, ‘You’ve just shared something difficult with me, and I’m not sure how best to respond.’ She can then say, ‘Well, I’m feeling vulnerable. What I’d really appreciate is having you validate me. I need to know you’re not scared off by what I’m sharing.’

“You can then say, ‘Ah, validating and acknowledging. I can do that. Unpause date.’ And then go on to do it.”

“This sounds so unnatural.” he said.

“It takes some getting used to, but it can be so helpful. I utilized this technique with my husband when we were dating,” I told him. “It was our second date, and I asked something about his history. He started sharing some personal stories.

“I asked if we could pause the date and said, ‘There’s something I want to say as a friend. We have no idea where this is going — we may never see each other again. And all this information may give you a vulnerability hangover. Perhaps it’s best to slow down.’ He was grateful for the advice.”

I taught Riki to compliment Shaul when he responded well to things she shared. “Thank you for saying that, it means a lot to me,” will encourage more of it.

On the flip side, if he responded monosyllabically, I told her to feel free to say, “Can you share a little more? I’m not sure what ‘okay’ means here. I need more words.”

Shaul and Riki kept dating and kept consulting with me. Things were moving along beautifully. Then Riki said something that disturbed Shaul. His usual affable self wanted to let it go, but I urged him to have the courage to initiate a crucial conversation.

“You can give Riki a heads-up. Ask her directly: ‘Can we have an awkward conversation?’ This lets her know that this may be difficult, but that you’re being mature and rather than just being pleasant around her, then venting to the shadchan, you’re having a direct conversation with her.

“Then, you can share whatever it is, be it, ‘Why do you consistently come late and never apologize?’ or ‘What did you mean when you said x?’ ”

Shaul tried it — and was grateful when the ensuing discussion was connective rather than divisive.

Two months later, Shaul and Riki had the most intimate conversation of all. “Will you marry me?” he asked, and she responded with a resounding “YES!”

Dating is like peeling an onion — every time you go out, you should be getting to know another layer of each other

All coaching scenarios in this series are real, but the characters are composites.

(Originally featured in Family First, Issue 931)