I took a family history. Shaul was the ben zekunim of a family of boys from Texas. His father was an intellectual, and his two older brothers left for yeshivah on the East Coast when Shaul was little.

The family was warm and loving, and he had a healthy connection with his parents, but it was a home focused on action, not emotions. Feelings weren’t discussed; love was demonstrated through caring actions but rarely expressed. He saw good middos, respect, kindness, but not emotional connection.

And then he’d left for yeshivah at a young age. There, he spent a lot of time building his learning skills, but that wasn’t setting him up for an emotional relationship with a female.

“What would you do when you’d come home?” I asked.

“My mother would want to hear all about my day, but I’d just tell her everything was fine, then go play ball with the guys. Supper was pretty quiet, my father would go to Daf Yomi, I’d do homework, and my mother would clean.”

Most boys learn to express emotion through watching others — particularly the females in their lives — express themselves. But in an all-male household with a father who spoke little and a mother whose talking was looked down upon, Shaul didn’t have this opportunity.

I had Shaul start by noticing what he was feeling physically — hungry, tired, cold, etc., which we discussed on our next call. Next, I had him keep a Feeling Log. Several times throughout the day, he was to jot the feelings down. I also had him observe how he felt around the people in his life. To open his mind to the options, I gave him a feeling wheel, a visual tool that organizes emotions into primary categories and detailed subcategories.

We’d meet over the phone every week or two for an hour. For the first few weeks, Shaul struggled, and during our weekly meetings, his log often read: “Fine, happy, okay.” But with gentle encouragement, he branched out into more nuanced emotions.

Next, I had him list at the end of each day four things people had done that he’d liked and four that he hadn’t liked. When he called me back for his next session, he was upset.

“One thing everybody will tell you about me is that I’m a nice guy. I get along with everyone and I want to keep it that way.”

“What’s the problem?”

“Well, this list… it’s really getting to me. It’s making me think about upsetting things! Why on earth would I want to get myself upset?”

“I hear you. Feelings can be scary when we allow ourselves to experience them. But ‘motion’ is at the root of the word ‘emotion.’ Feelings pass. In fact, the only way we can get past them is to first feel them.

“If you see something is consistently upsetting you, try to consider what’s beneath the feeling — and if there’s anything you can do about it.”

The next week, he sounded buoyant. “There may be something to this touchy-feely stuff after all,” he said. “You won’t believe what happened.

“One thing kept appearing on my list. My morning seder chavrusa always comes late. It really frustrates me. When he saunters in at nine fifteen or nine twenty, the whole morning seder is sluggish.

“After writing it down for a week and getting more and more annoyed, I finally decided to say something. When he came in close to nine thirty, I said, ‘When you come late, it’s hard for me. I feel like it impacts my learning the rest of my day.’ ”

“Wow, good for you!” I said. “How did he take it?”

“Actually, he was shocked. ‘Whoa, man,’ he said. ‘I had no idea it bugged you. You never said a word so I figured you were chilled about timing.’

“We talked about it. He told me that he struggles to get up on time, but if it’s important to me, he’s going to work on it. And ever since, he’s been much more prompt!”

“Amazing! Feeling that frustration was unpleasant, but look at the results.”

“You know, starting seder on time isn’t the only result,” Shaul said slowly. “I realize that the unexpressed frustration was like an invisible wall between us. Now that we talked it out, I feel closer to him.”

Soon, his newfound skills were impacting other friendships, too. Previously, if a friend would share feelings, Shaul would wait quietly for him to finish because it was so uncomfortable. As he became more at ease with his own emotions, he was able to lean into what was being shared and listen empathetically. He began both offering compliments and speaking up when things bothered him.

Now it was time to build conversational skills.

“When girls say, ‘I’m just not feeling it, I don’t feel connected,’ about their dates, it often means that the relationship is staying surface-level, without one or both of you sharing your inner world,” I told him.

I brought up various issues a girl may share on a date, and we discussed potential responses, so he could learn what girls wanted and needed in a conversation.

We also discussed active listening. “Active listening means going beyond two-word comments or yes/no questions,” I explained. “Engage by following up the stories or revelations she shares with open-ended questions that encourage meaningful conversation.”

To practice, I encouraged him to speak with his mother more often and respond thoughtfully when she expressed her feelings, rather than dismissing them.

“That’s so girly,” he protested.

“Yes, it is. And news flash: You’ll be marrying a girl. This is great practice.”

A few weeks later, he was all in. “My mother is such a wonderful person,” he shared. “I’m realizing it so much more now that I’m getting to know her on a deeper level.”

Their conversations opened his eyes to the world of emotions and gave him a fresh perspective on the things going on in his life.

“I always thought that feelings weren’t manly and should be shunned, but I see now that my mother has so much to teach me.

“Forget a wife; you’ve given me my mother.”

It was deeply gratifying to hear that. However, Shaul still needed a wife. After six months of intense work together, it was time for him to restart the search.

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

(Originally featured in Family First, Issue 930)