Z aki was considered a very successful guy by many measures. He was a shrewd businessman and was making great money as an investment banker. He was also still a good learner and was known for giving nice derashos at family gatherings and shul events.

Still good-looking and a sharp dresser, he piqued the interest of many single women who were interested in finding out why he was still available. And yet in spite of this, there wasn’t a single shadchanit in town who was going to waste her time with him.

“Zaki’s not ready to settle down,” was the kind of thing you’d hear. Not that I was asking, but it was a frequent enough topic of discussion that you couldn’t go to a Kiddush at the local shul without hearing at least someone talking about who just wasn’t on the market.

It wasn’t because he wasn’t frum or had unacceptable hashkafos. Nope. Zaki made a siyum every few months and had it catered by the restaurant with the best hashgachah in the area. He was always one of the first at minyan in the morning, a regular at the halachah shiur downtown, and happy to pinch hit as a substitute in the Talmud Torah on December 25 when the math and science teachers had the day off.

I had to be honest — I was pretty interested in finding out about him myself, when he called me to set up an appointment.

Actually, I should correct that one: He didn’t call to set up an appointment. Rather, his sister called to set up an appointment for him, “because if he’s still single he must be crazy!” Either way, I was interested.

Zaki came in wearing a particularly sharp outfit — a tailor-made custom suit and a purple pastel shirt with a matching handkerchief in his front pocket. He was pleasant enough on introductions but it was clear he had no intention of starting some long-term insight-oriented therapy.

“Doc, I gotta be honest that I’m here because my sister’s been bugging me to come in for the longest time and I figured this was the easiest way to get her off my back. Can we just get this over with so I can get back to the office by 1:30?”

I was willing to help him get back to work in time for the lunchtime minyan and told him I only needed him to answer a few questions to confirm that he didn’t need a psychiatrist. I fired a bunch of standard ones in rapid succession to ensure that there were no symptoms of mental illness, no addictions, and no weird thoughts.

“You’re basically okay, Zaki,” I said. “Certifiably stable as far as I can see.”

“You can get all of that in 13 minutes, Doc?”

“Sure. I mean, why not? I’ve been doing this for a while and you’re in a rush, right?”

Zaki nodded.

“Okay then, Zaki. It’s been a pleasure meeting you, I’ll tell your sister that all’s well, and please don’t hesitate to be in touch in the future if you ever develop a compulsive gambling problem or anything else that could use a good shrink.” I figured that a bit of sarcasm would get him going, as my chance was running out.

“Okay, Doc, thanks for everything,” he said.

I waited for a moment and looked at him. I’d been doing this for long enough by now to know that a guy like Zaki would do the heavy lifting for me most of the time.

“Doc?” he asked hesitantly. “Don’t you want to know why I’m not married yet?”

“Only if you want to tell me,” I responded. “I’m not here for gossip, I’m just here to help folks if they want to talk. Is this something you wanted to talk about?”

“I don’t know. Maybe?”

“Do you want me to say it, Zaki? Do you want me to ask you why you aren’t married yet?”

Zaki blushed. I didn’t know whether to push him or not so I figured I’d let him make the next move.

“I just don’t know what to say. I’m just waiting for the right girl. I know this is going to sound like I’m a baal gaavah, but I just kind of figured that I’m a bit of catch.”

“Really? That’s it, Zaki?” No history of abuse, no broken childhood, no questions of attraction or anything of that sort. “You’re just waiting for the perfect girl?”

“Well, I mean I’m kind of a catch myself, like I said.”

“Yeah?”

“Well, I learned in good yeshivos, come from a good family and have good parnassah, and I still do the daf. I’ve just kind of figured that—”

I generally avoid interrupting my patients but this was a once-in-a-lifetime moment for a serious mussar-potch. “Zaki, really… you still think that the 19-year-old beautiful girl who is a direct descendant of the Chofetz Chaim wants to marry you?”

“Well… I mean… I—”

“Zaki! Really! You think that the 20-year-old great-granddaughter of Rav Shach is dying to marry you?”

“I—”

“Zaki, you’re 43. You’re going bald. And you’re only looking slightly out of shape because your tailor-made suit hides the spare tire…”

“I—”

“Zaki, just get with the picture and be lucky that anyone will want to marry you! It could be that you’ve missed out on a million good shidduchim by now. But if you don’t pull the trigger soon you’ll be the best catch to never walk the aisle and stand underneath the chuppah. You’ve been single for so long that you’ve got all of your grandparents to name kids for!”

“I—”

“Zaki!” I started again before he took his turn to interrupt.

“Okay, Dr. Freedman! You’re right!”

“Yep,” I told him and then kept quiet.

Because most of the time a guy like Zaki has some serious issues underneath his carefully-sculpted projection as the perfect catch, and fear is usually at the core: What was it with Zaki? A fear of commitment? Of interpersonal or emotional intimacy? A fear of missing out on something better? A fear of responsibility? Of losing his perceived freedom and not being able to do exactly what he pleased exactly when he chooses? There were surely walls of self-protection that had been built slowly over years of being a bachelor, and those walls wouldn’t come down so easily.

“You’re right,” Zaki said again and then sat silently for at least a few long minutes before he said a third time, “You’re right.”

“But I don’t want to be right this time, Zaki. I just want an invitation to stand in the back of the wedding hall and smile at you when you break the glass under the chuppah.”

“B’ezras Hashem,” he said half-heartedly.

“B’ezras Hashem,” I responded, “But only if you’re willing to do your hishtadlus, Zaki. Now it’s time for you to get back to the office. Keep in touch if you’d like to schmooze again some time.”

As of today, there still hasn’t been any follow-up and Zaki is still on the market — he obviously didn’t care too much for my mussar, even as I tried to leave the door open for something deeper.

Would he ever come back? Would he ever get married? To be honest, I wasn’t holding my breath.

Originally featured in Mishpacha, Issue 668. Jacob L. Freedman is a psychiatrist and business consultant based in Jerusalem. He serves as the medical director of services for English-speakers at Bayit Cham, a national leader providing mental health treatment and outreach within the religious community. Dr. Freedman can be reached most easily through his website www.drjacoblfreedman.com.