“That sounds so incredibly painful,” I said. “To go through that again and again….”

“Yeah, it’s miserable,” he said quietly. But Shaul didn’t stay in a negative space for long. “It seems the problem is me. And that’s why I’m here. The last girl I dated told me you helped her and suggested that I call you. So here I am, ready to work.”

“Love that attitude!” I told him. “Look, Shaul, there are two ways we could play this. I could start from the very beginning and ask you lots of questions about your dating patterns. But here’s the thing. Having coached your last date extensively — and recognizing this pattern as one that often comes up for guys, I’m pretty sure I know what might be the problem. I could just say it straight, but it might hurt.”

“Well, isn’t that convenient. Seems like your having coached my dates saved me a few sessions.” He gave a wry chuckle. “Hey, I can handle it. Just tell it to me straight; do the pull off the Band-Aid thing.”

“Sure, if that’s what you want. Let’s start by discussing what the normal progression is during dating, and then we’ll zoom into where you may be getting stuck.”

There are four stages couples go through as they move from first date to marriage. I outlined them for Shaul:

Getting to know you: This is the early stage of dating, those first few dates when you’re gathering information, getting a sense of the person, and seeing if there’s a baseline of compatibility. Here, you’ll learn about their family, schooling, camp, work/college/yeshivah. You’ll decide if you want to get to know them better.

Building a friendship: After the first few dates, the next step is to build a friendship. Here, you discover if you share interests, if you’re on the same page hashkafically, if you enjoy each other’s company. You start opening up and sharing more personal details and stories. You look forward to seeing each other. This stage leads to, “I really like you.”

Emotional Intimacy: Friendship is wonderful, but marriage needs more. In stage three, we get vulnerable, sharing what it was like growing up in our homes, struggles we’ve had, hopes and dreams. This is the stuff you’re not sharing with casual friends, things that are more personal and sensitive. In this phase, it’s really important that both people feel safe and heard. This vulnerability leads to deeper connection. At the end of this stage, people feel like, “I see strong marriage potential here.”

Taking the Leap: This is where you move from thinking you could marry this person to wanting to marry them and moving into proposal and engagement.

“People get stuck at various stages,” I told Shaul. “You do a fabulous job at the getting-to-know-you stage. And you’re also able to build a strong friendship. In fact, the girl you just dated told me, ‘If he was a girl, we’d totally be friends, he’s nice and kind and funny. I really like him.’ But they couldn’t get further than that.”

“That’s nice,” he said quietly. “I guess that means my problem is when it comes to the emotional intimacy…. To be honest, even that phrase makes me kind of nervous. Like, what do you want from me?”

“You said it, not me. And yes, that does seem to be where things break down. A spouse is a lot more than a friend; it needs to be a deeper, stronger relationship. Particularly for girls, having a husband who will be emotionally engaged is usually a deal-breaker.”

“Can you give me an example? I know this sounds silly, but I’m not ever entirely sure what you’re talking about.”

“There are no silly questions here; all questions are good. And sure, I’ll be giving you lots of examples. Let’s imagine a girl just shared with you that she was bullied all through high school and tells you some of the painful experiences she had. How would you respond?”

“Uh, what is there to say? I’d just listen quietly. I mean, I’d feel bad for her, of course, but what am I supposed to say?”

“Good question. When a girl opens up about something painful, she’s a little scared. She’s being vulnerable and letting you see a part of her that she doesn’t share with everyone. At that point, she needs validation. She needs to know that she was heard, that you feel for her pain, and that you don’t think less of her or look down on her because of her struggles.

“There are a few ways you could express that. It could be something like, ‘That sounds so difficult, I appreciate you sharing that,’ or ‘Ouch, four years of being excluded! That must have really hurt!’ or you could ask a question. ‘You must be so strong to have gotten through that, what helped you get past it?’ All of these responses help her feel heard.”

“Ohhhhh.” A long silence. “Um, yeah, I’m not good at this stuff.”

“Well, we just jumped into the deep end,” I said. “Let’s take a bunch of steps back. Next week, we’ll talk about emotions in general and how to get in touch with our own. If you’re not in touch with your own feelings, it’s impossible to connect with another person emotionally.

“Also, you may want to take a dating break for a few months. It’s hard to focus on learning new patterns when you’re also trying to navigate a potential relationship.”

“I’m happy to take a break — getting ditched again and again is not exactly my idea of fun….”

“We’ll work on this together,” I promised him, “and hopefully, once you can get to — and past — stage three, some lucky girl won’t ever want to ditch you.”

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

(Originally featured in Family First, Issue 929)