"Everyone wants to date him, but no one wants to marry him”

Father: His teachers always told us Jack was bright, and a “leader,” but without interpersonal skills like empathy and kindness, I think that “leadership” flipped to “bullying.”

Shelly: I get feedback from the shadchan. Jack knows how to spend money and charm people, but he makes all the decisions. One girl said, “He’s great but he knows it.”

Jack: I’m not the one who needs therapy — those girls are!

Shelly sounds apologetic when she schedules an appointment for her son Jack. “I know this is a terrible thing to say,” she stammers, “but I think there’s something off… his personality… social skills… You decide. I just wanted to tell you that before we meet.”
When they arrive, Jack slides easily into the seat opposite me. As he drapes an arm over the back of a chair, his Rolex glints in the light.
I offer my standard opening. “What brings you here?”
“My mother,” he drawls.
“Nah,” Shelly says. “Jack brought me here. In style — new car.” She’s trying for a light tone to cover the tension sizzling between them.
I chuckle. “How can I help you?”
“My mother wants me to get married,” Jack says. He rolls his eyes and smiles conspiratorially. “Such a Jewish mother.”
Shelly stiffens. “And you don’t want to get married?”
“Of course I do. I date all the time.”
“That’s the problem!” Shelly turns to me. “He dates all the time. He has no shortage of dates.”
I glance at Jack. It isn’t only the expensive clothes; he has an easy confidence and undeniable charm.
“What do you do?”
“Going for my MBA with a specialty in business analytics. My father owns CapitalVentures. I’ll be working with him as soon as I graduate.”
“Everyone wants him for their neighbor or their niece,” Shelly continues. “But he’s 24 and still not married!”d
“I’m only 24, Mom,” Jack says. There was an edge in his voice. “Why is that a problem?”
I look at Shelly. “Why do you think there’s a problem?”
“Okay, not a problem…” Shelly says, “but a pattern. Everyone wants to date him, but no one wants to marry him.”
Jack looks angry. “I just haven’t found the right one yet!”
“They all say no after three dates. Five, tops.”
“Who needs them?” he mutters.
“Which qualities do you think a successful businessman has?” I ask Jack.
“Connections. Money. Brilliance and innovation.”
“What about marketing and accounting skills?”
“You can hire a marketer and accountant. They’ll know the things you don’t.”
“That’s right. Everyone knows things you don’t know, can do things you can’t do. Your wife isn’t going to be just another accessory like your fancy car and your cool shoes. You need to realize that and approach dating with that perspective.”
I ask Jack to name his strengths.
“Intelligence. Public speaking. Business savvy.”
I ask him to rank himself out of 10 for each trait, and he ranks himself 9 or 10 for each.
“What about things like kindness and empathy?” Jack ranks himself five on each.
“How do you think others might rank you on these traits?” I let him think for a minute, planting the seed that he might be inflating his ratings. “The girls you date, for example. And what do you think they value more; public speaking or empathy?”
It’s quiet for a long minute. “Okay,” Jack says finally.