Neuberger, who learns in Ner Israel’s kollel and has an administrative position in the yeshivah (he’s the grandson of Ner Israel’s founding president Rabbi Naftali Neuberger a”h), admits that even at 30 and above, it’s still a guy’s market. “I once met someone — it didn’t work out but I wanted to help her. I told her, ‘You’re overqualified. You need the best guy in Brisk who also has a PhD on the side.’ She said, ‘I just want to marry someone normal.’”

In the end, he married one of those “overqualified” young women — a physician named Chani Weinstock. “Actually, we went out four different rounds over seven years — the first three times she said no. The fourth time it clicked.”

Round Two

Reviving a failed shidduch actually has a pretty good track record for older bochurim, as 32-year-old Yehudah Mohadev of Jerusalem can verify. Earlier this summer, he married a girl he’d first met five years ago.

“I saw that the suggestions I were getting were pretty much the same, that there was nothing dramatically new on the horizon, so what was I looking for? Something that didn’t even exist? So I backtracked,” Yehudah says, “and I called the shadchan who had arranged the shidduch five years before. Five years might sound like a long time, but when I look back on it today, I know that we hadn’t been ready when we first met. In all likelihood, we both needed to go through things to get us to this point. I’m not saying every older bochur should go through his list and see what can be started up again. What I would say is that older singles should keep an open mind and to try to think about what other forms of hishtadlus they can try. For every person, the answer might be different.”

For Yehudah, who learned in Kfar Chassidim-Rechasim for eight years before moving to a yeshivah in Jerusalem, the constant disappointments while everyone around him seemed to be moving forward was compounded by the fact that at age 30, he was ready to look for a part-time position in chinuch. But, as he discovered, “many places will offer a teaching position to a 30-year-old avreich without thinking twice, but not if he’s single. That leaves you in the same place as you were at 20. Even your daily schedule doesn’t change; you learn in the morning, you take a nap in the afternoon, and then you get up and go on to another seder. I love learning, and that’s what kept me going, but I can’t deny the fact that when I saw all of my friends getting married, I felt like I was the one left behind.”

Once a learning bochur hits 30, the conventional wisdom is that, obviously, he’s too picky — he’s probably been offered a slew of girls, so why can’t he just say “yes”? For Yehudah, it’s a sore subject. “Why does everyone accuse us of being too picky? Why should I get pressured to meet someone just because the shadchan insists, even though I know it’s not what I’m looking for? A bochur needs to go at his own pace, to make his decision with peace of mind, and with emunah that he’s on the path tailor-made for him. That’s what kept me going — my trust that Hashem was leading me to the best place for me, and I made sure to learn at least two sedorim every day. Those are the things that gave me strength. Without them, I would have collapsed.”

Still, not every shadchan wants to invest in this particular demographic. It’s much easier to deal with young people starting out in shidduchim, where the efforts are more likely to end with a broken plate instead of a bad date.

“There are some months where I arrange dozens of dates,” says Raizy K., a shadchanit who lives in Ramat Beit Shemesh and specializes in the over-30 single population. That sounds like a major success rate, but Raizy admits that in over a decade of this work, even after thousands of dates, she’s made just ten shidduchim. “That’s why most shadchanim won’t deal with this age group. It’s very disheartening.”

Raizy says she fell into this line about ten years ago when she made a shidduch for a close family member. He brought his roommate, and the roommate brought his best friend — and soon, Raizy had filled up a notebook of suggestions.

Because most of these bochurim have been meeting girls for years, Raizy says she tries to get them to think out of the box. “There was a boy in Mir who wanted a very particular shnit. He was very smart and wanted a really brilliant girl. I set him up with this amazing young woman — she had a PhD — but she was also seven years older than him. Well, today they’re happily married.”

Raizy is also a pre-marital counselor and first-year marriage coach (couples who marry when they’re older bring a different set of issues into the marriage than do those who marry at 20). True, she says, bochurim resent being told that they’re too picky, and legitimately feel that they have good reasons to reject suggestion after suggestion. But what she’s discovered — after extensive systematic interviewing — is that the longer the bochur waits, the higher his expectations. “He’ll tell me ‘I’ve waited so long, I really want her to be perfect,’ or that he doesn’t ‘feel the fireworks,’ although a lot of that comes after marriage, or that he’s not attracted — but what that often means is that he’s created an image of what he considers beautiful and isn’t always willing to look past that to what creates real attraction and connection.

“Still, this is the crowd that needs chizuk and direction the most,” she says. “My bottom age limit is 25 — younger people have so many shadchanim out there, they don’t need me. With this group, though, I can be helpful and make a real contribution, even though most dates wind up being dead-enders.”

Worth a Try

Pinny Tzarfati, the 35-year-old “alter bochur” of Yeshivas Kol Torah in Jerusalem until his marriage last year, was never defensive when it came to shadchanim accusing him of having unrealistic expectations or encouraging him to get help for what they termed “commitment issues.” In fact, he encouraged professional counseling for his friends, sought help for himself, and encouraged roshei yeshivah from other institutions to set up vaadim that would specifically address the subject of shidduchim.

“I think it’s vital for rebbeim to sit with bochurim and discuss priorities in choosing a shidduch, and to give them ‘Jewish Home’ classes similar to those given in seminaries. We’re now examining how to implement this idea in yeshivos.”

Pinny, who was in shidduchim for 13 years, says he never felt things weren’t moving forward, just that his time hadn’t yet come. While in yeshivah, he made sure not to stagnate emotionally, filling his need to nurture by learning with baalei teshuvah from a nearby yeshivah, working as a counselor in a special-needs residential institution, and taking courses in special education. “I felt I was helping others, and that I wasn’t just ‘waiting around,’ remaining stuck in the same place.” And when the right shidduch finally came around, it too was a reopened suggestion from four years before.

Making sure to keep going forward is vital for an older bochur still in yeshivah who wants to stay in the shidduch loop, agrees Raizy K. “As girls get older, they might earn another degree, make more money, expand their social circle, volunteer, take trips, and so on. They really blossom, while as the men age they seem to stagnate — same yeshivah, same routine, and on many of them it is noticeable,” she says. “My recommendation is to add some spice to life, learn something different on the side, volunteer during off times, take on a hobby, and most important, learn to be other-focused. When you focus on giving to others, whether it’s a smile, a compliment or a helping hand, it enhances your life so much more. I tell singles I coach that we are who we are not in spite of what we’ve been through but because of what we’ve been through. How we handle the hand we’ve been dealt in life is what makes us who we are — so let’s lead meaningful lives.”

Dovi Zilberman, who left Israel for the US at age 33 to look for a shidduch because “I couldn’t take the pressure at home” (soon after, he became engaged to an Israeli girl who also traveled abroad for shidduchim), doesn’t deny that many older bochurim — at least his own friends — have certain issues that prevent them from moving on.

“Look, I know lots of older single boys and my wife knows many older single girls, and we’ve been trying to make shidduchim without any success,” he says. “Single men in this age bracket tend to be very picky, often without good reasons. Sometimes they reject suggestions — at least the ones we’ve made — because of trivial details.”

That’s why Jerusalem shadchan Ravi Shachar says that all those years of dating don’t necessarily give alte bochurim a better perspective on what they’re looking for. “Sometimes,” he says, “it just makes them more confused. After all those years of dating, they don’t know when to say yes.” Shachar has his own niche — Anglo-bochurim and girls, or those from English-speaking families who grew up in Israel — and although he doesn’t give much hope to being the shaliach for this older demographic, he good-naturedly never refuses a client.

“You never know,” he says, “Sometimes a long shot will also work — it’s always worth a try. There was a boy in his mid-thirties who I gave many names to but nothing ever happened. Then someone called me from England about a 27-year-old girl who was going to be in Israel for all of two weeks. I just threw out the name to him… and she went back home a kallah.”

Expiration Date

Fifteen years ago, shadchanim already had their eye on Yossi Aharoni, a top bochur at Yeshivas Beis Mattisyahu, but for some reason, his siblings wound up skipping him and he was 37 when he finally stood under the chuppah earlier this year.

Fifteen years of suggestions, of hopes, of letdowns. “Over and over, there are times you think that something is about to succeed, and then you find yourself falling again. You pick yourself up after a disappointment, but then you get excited again when it seems something is about to happen, and then you find yourself even more despondent when it fails once again. At the age of 25, and then at the age of 30, and then even at the age of 37, you find yourself returning to the starting point over and over again, and you never know when it will end.”

The most painful times, he says, were the times that should have been serene and spiritual — like walking down the street on Friday nights seeing married men, a decade younger than he was, holding their children’s hands. “I tried to fortify myself internally and to train myself not to measure my own life against the rest of the world. I tried to remember that I should enjoy the things I had. And I tried very hard, as ridiculous as it sounds, to enjoy the experience of shidduchim itself.”

Yossi’s always been a top learner, but he says, “It’s very hard to remain in a yeshivah framework under the circumstances. You’re living in an apartment with ten other bochurim, and the day comes when you turn 27 and you realize that all the other bochurim in your apartment are 23 or 24 years old. Every year sees a new collection of boys, and every year they share their personal lives with you. They feel that you’re their best friend and they even invite you to their aufrufs, where you deliver beautiful speeches… and then they disappear. With the new year, a new crop of bochurim arrives, and the entire pattern repeats itself. That’s one reason I left Beis Mattisyahu and transferred to Mir,” he relates. “In Beis Mattisyahu, I felt that I had reached the end of the game.”

Yossi admits that people tend to judge older singles, but says it’s not fair to pass judgment — and not everyone is too picky or afraid of marriage. “I would say the main problem that plagues older single men is the inability to make decisions. Sometimes they have trouble choosing their socks. You can see them buying a tie in a store and then returning it two days later. It’s very hard for them to make decisions, especially the most significant decision in life. Furthermore, they often look at a shidduch as if it were a prize, thinking about what others will say. That causes them to disqualify girls from certain backgrounds, of certain ages, or in certain life situations. There are also many singles who suffer from an emotional block and have difficulty opening up to others.

“There’s a story about a dog that was wandering around in a dark forest and suddenly heard the howling of a wolf,” Yossi continues. “The dog was frightened at first, but then it decided to mimic the wolf’s cry. The two animals continued howling at each other until the sun rose, and then it became clear that they were actually both dogs. You see, when the parties in a shidduch become concerned and suspicious, the real solution is for them to gradually remove their masks. That’s what worked for me.”

Yossi’s father, Reb Dovid Aharoni, is a marriage counselor and lecturer, and Yossi says that what steered him on the right path was attending his father’s lectures. “I definitely became wiser as a result,” he says. “And I would advise any bochur over 25 to do the same. It opens your eyes to the true nature of marriage.”

When Yossi’s bashert appeared, he says he was finally able to put aside what others would think, what kind of impression the shidduch would make, and instead focus on what was truly good for him. “Finally, I was at peace with myself. And this is what I want to share: Shidduchim are not as easy as younger bochurim think, but they’re also not as complicated as older singles believe. Every person should do the minimal hishtadlus and then allow Hashem to lead him. Just do yourself one favor: Don’t try to interfere with the things He is doing for you.”

—Rachel Ginsberg contributed to this report

(Originally featured in Mishpacha, Issue 720)