New-Old Concerns

Chana says that the basic elements of every shidduch are the same, no matter what age the parties. “Two pieces of wood don’t get married,” she says. “At any age, there must be chemistry. Especially these days, when women generally have parnassah, people don’t get married for convenience.”

Cultural identification is often less important to mature singles. Chana ticks off successful middle-aged shidduchim that wouldn’t have come about had the pair been 20 years younger: the Lubavitcher with the Mirrer, the chassid with the more worldly wife. “They’re not raising children together,” Chana points out. “Their hashkafos don’t have to match 100%.” As long as both partners are respectful of each other’s principles, a wider disparity in “type” can work.

The possibility of relocating is a concern that crops up frequently. Unlike younger singles, who have fewer family and career ties, and greater energy, mature singles often have children, established careers or businesses, and well-developed networks in the places they’ve lived for decades, making it more challenging to move. Additionally, in cases of divorce, points out Daniel, custody agreements and visitation schedules can restrict a parent’s movements.

On the other hand, distance can sometimes be leveraged to a couple’s benefit, says Ruchama, a successful shadchan from L.A. When logistics of two established lives clash — married children or aging parents on opposite coasts, or a job just a year or two away from retirement in a remote city — geography doesn’t have to be an obstacle to a relationship. “I’ve watched older couples transition slowly into living full-time together,” she says. “It can really work when the partners take the time to fly back-and-forth — one Shabbos here, one Shabbos there, a week together and then two weeks separate.” Pointing out that second marriages statistically have a much higher failure rate, she maintains that a slower pace of adjustment can help couples navigate the hurdles of joining two very different lives.

Finances still matter, but in a very different form than they used to. While twenty-somethings may need to discuss college and career plans and whose parents are supporting, middle-aged singles have a different set of financial concerns.

To women in their fifties and beyond, a stable income is very important, says Daniel; energy and ambition are no longer enough. Frum life is expensive, and few women are eager to tie their lives to someone who has drifted aimlessly from job to job with no solid financial footing.

Singles might also be concerned about issues such as taking on the financial burdens of another family’s children or mortgage, whether or not to merge finances, and how to deal with pensions or life insurance policies from former spouses.

It’s advisable to draw up prenuptial agreements outlining these decisions. “What you don’t want happening is for the couple to discuss finances right before the wedding and break up,” says Ruchama, who has unfortunately seen this happen. “Discuss finances before getting engaged,” she warns.

What Really Matters

While some singles realize that a healthy spouse with good middos is the only thing that really matters, others come with a list of requirements, and at that late stage, it can be hard to be flexible.

“In general, a lot of superficial requirements fall to the side,” says Chana. “You have a lot fewer drishos v’chakiros.” But while plastic tablecloths may lose their significance, there are still a number of weighty concerns that stand in the way of a successful shidduch.

Sharona, who is in shidduchim for the third time, sees it this way: young people look for potential, but there isn’t yet much substance to the person. By the time a person has lived several more decades, nebulous potential is no longer enough. In her view, women are looking for someone who has made something of himself, while men are still stuck on what they were looking for in their twenties and thirties.

Many shadchanim agree that men have a tendency to search out wives younger and prettier than befits their station in life.

Speaking of his eight-year sojourn in shidduchim, Yaakov recalls both men and women who were loath to compromise. “I know a great guy, sharp, good-looking, a hard worker with his own business, but he’s looking for someone too young and perfect. Chemistry is important, but can come from unexpected places.” Be open to different appearances, he advises. Neat and clean is important, but Hashem might have a different look in store than you anticipated.

“It’s in your best interests to marry someone within your decade,” agrees Chana Devorah. “If you have two decades more life experience than your wife, you’ll be mismatched on many levels.”

On the flipside, in their concern for financial security, women sometimes get hung up on a potential partner’s level of education. While intelligence is a factor in whether they’ll enjoy each other’s company, at this stage in life, formal education is no longer quite as relevant, notes Daniel.

Bottom line? “You need to open your mind, venture out of your comfort zone,” says Chana Devorah. “Everyone says they want a baal middos, but some people prioritize so many other requirements that they might never get to that.”

The Children Challenge

One major factor in mid-life shidduchim is the second generation.

A cliché in the shidduch world is the man in his mid-fifties or even sixties who still hopes to have children. Chana Devorah wishes they would remember that children are from Hashem, and no one truly knows what the future holds.

Others, though, are more wary of the demands a young family will make on their lifestyle.

Yaakov, who reentered shidduchim after his divorce at age 50, knew very clearly that he was not prepared to raise little kids again. “I already had kids. I didn’t want to be changing diapers in my fifties and sixties, or walk a child to the chuppah at age 70 or 80.”

When he was introduced to his future wife, he wasn’t excited to discover that her youngest was only 11.

“To be honest, I didn’t want kids in the house. But I became flexible, and Shmuli ended up living with us until he went to yeshivah. Not every day was perfect, but we worked really hard, and it’s an incredible gift. I’m the luckiest guy, baruch Hashem.”

Marrying a spouse who already has children, whether or not they live with the parent, is fraught with potential pitfalls — but they’re surmountable.

Daniel relates that when he reentered the shidduch scene after his divorce, he initially hoped to avoid the complications of a blended family. “It didn’t take long for me to become more realistic,” he says. “I realized, I’m not going to find this, I need to start compromising. Now, as a shadchan, I have to coach people and bring them down to earth.”

He also learned that marrying someone without children is no guarantee of smooth sailing. One man he knew married a woman with no children of her own. Having no experience with kids, she experienced a great deal of friction with her step-children.

This couple’s heartache might have been avoided had her husband observed her interacting with his kids before finalizing the shidduch. Daniel emphasizes the importance of the couple getting to know each other’s children. By seeing the potential spouse’s interactions with their children, a single can get some sense of the other’s parenting approach. Ideally, he says, the children should meet and get to know their potential step-siblings, too.

How can a single know if a potential partner’s family situation is something she’ll be able to handle?

Chana Devorah says the most important thing is to be prepared. “Just like someone marrying a Hatzolah member would need to be someone capable of managing when her husband runs out on emergencies, someone marrying into a family with children needs to know she has the physical and emotional strength to manage a blended family.” She should also consider whether the father has the backbone to support her in her parenting.

Which ages need to be handled the most delicately?

Young children are the most pliable, and will adapt more easily to a step-parent or -siblings. And just like in more typical nuclear families, teenagers are often the ones who require the most sensitivity. “Not everyone can do it,” acknowledges Chana Devorah. “Be prepared for the realities, and be committed to getting guidance every step of the way.”

A specific niche requiring extra sensitivity is the teenage or young adult daughter who’s been running the household in the absence of a mother. Chana Devorah knows people who won’t consider a shidduch prospect until the youngest daughter marries. “She’s been running the house for years; you’d be intruding her territory,” she explains. “To manage that successfully, you’d need to be an excellent communicator — and have a lot of siyata d’Shmaya.”

Even if a couple’s children are already married, they still add a layer of complexity to a shidduch.

“What really makes or breaks a second marriage is the kids,” says Rivka, who is happily married after 14 years of widowhood. “I once went out with a really nice guy who told me his kids weren’t excited about him remarrying; that’s a red flag.

“It’s selfish for kids not to realize that an ‘older person’ needs a life too, and can’t just revolve around his children and grandchildren. I credit the success of our marriage to our having mature adult children who realize the best thing for us is to be happily married.”

However supportive the children are, everyone will still need to learn to navigate a new dynamic. Married children may be used to hosting their father every Yom Tov, or relying on Bubby’s willingness to babysit. Remarriage threatens the status quo: Will they be shut out when Mommy begins to spend time with a new husband?

“Even though they want their parents to get married, not all kids handle it well,” says Chana. “A second marriage displaces them to a certain extent. It’s hard to share your parent with some stranger.”

Perel says that the key to solving these hurdles is no different than in any other marriage. “Marriage is about being flexible and meeting in the middle. This is sometimes more difficult for people who’ve been single for a long time, and are used to being independent. But with a good spirit, a sense of humor, and if you’re working with someone kind, caring, and flexible, you can make it work,” she says.

Getting It off The Ground

Interestingly, the technical aspects of a shadchan’s job are often easier with mature singles, says Chana Devorah.

It’s simpler to arrange dates between mature singles, who are generally on less frenetic schedules than their younger counterparts. Instead of being in school while working or trying to establish a career, mature singles may be retired, or focused on only one or two commitments.

She also finds them more motivated to exert themselves. “Younger guys will say, ‘Can you find me someone where I live? I don’t like to travel,’” she says, while some of her older singles will drive eight hours or more to pursue a promising shidduch.

Perel says that after providing the initial idea, the shadchan’s role is usually less hands-on. “I say, ‘Here’s the number, let me know what happens.’”

While Chana Devorah does generally facilitate the logistics of the first date, after the second, the couple usually communicates with no intermediary.

Still, an experienced shadchan can help resolve difficulties that arise. “A lot of people think that if they’re intelligent, they don’t really need a shadchan,” says Daniel, “but the shidduch system works. A good shadchan can help move a shidduch along at any age.”

Since dating in middle age has fewer rigid rules, it can be a little disconcerting for singles to find their footing, but the more relaxed protocol can be liberating. Before her first date post-divorce, Resa Fogel remembers wondering, How am I going to do this? I haven’t been on a date in 30 years! What will I wear? “On the date, I asked him, ‘What are the dating rules?’ and he said, ‘You make up your own!’”

While questions about camp and seminary experience fall off the radar past a certain age, certain avenues of investigation do need extra care in older age brackets.

Many singles at this stage are divorcees, which necessitates an additional layer of delicate investigation.

“A red flag is any husband that tells you that his wife was crazy,” says Chana Devorah. Usually, this is hyperbole that doesn’t reflect well on the middos of the speaker. In the uncommon case of genuine mental illness, a rav should be consulted about what information may be shared and with whom.

Women, too, need to be careful not to spread reports of abuse that aren’t strictly factual or necessary. Aside from the issue of shemiras halashon, exaggerated claims erode the credibility of the majority of women whose stories are true. Chana Devorah maintains that baalei middos of either gender know to restrict hurtful information to a need-to-know basis.

Another warning sign, says Chana Devorah, is the single father who has custody, and tells people that his wife lost the kids because she was (fill in the blank: unstable, incompetent, neglectful)

“People think if the man got the kids, he’s a tzaddik and she must be nuts,” she says. “No, no, and no. Angry men can be unethical, and custody arrangements aren’t always about how good a mother someone is, but can be about how well-connected the father is or how much he wants to hurt his ex.” Any time one spouse badmouths another, that’s a sign that some thorough and objective detective work is in order.

The Road to Happily Ever After

Faced with a daunting list of challenges, what’s a single to do to ensure a happy ending?

“Don’t sit and wait,” says Ruchama. “Use all the tools you have, even if that means going out of your comfort zone. Utilize frum dating sites or travel to a different community each Shabbos. Go to classes in different shuls. Get a list of matchmakers and call them monthly. Treat it like a business plan,” she advises. “Be open to getting a dating coach if you’re having trouble.”

While waiting for the knight in shining armor to materialize, singles should stay positive and vibrant, says Yaakov.

“I continued to swim every day,” says the energetic 64-year-old. “It’s important to maintain a positive energy and a sense of humor. It’s a very tough road. You’ve got to keep moving forward and stay positive; Hashem is there to support you! When I teach people to dive, I tell them to stop thinking, just do it, it’ll be okay!”

Rivka emphasizes the importance of projecting positivity to others, as well. Despite the difficulties she faced raising her young family alone before her remarriage, she made sure not to bemoan her plight to the men she met.

Resa, a psychologist and shadchan herself, works hard to put this principle into action. “People tell me I’m a strong person; I wish I could believe that,” she says. What helps her bolster her confidence is reflecting on how far she’s come. When a cantankerous furnace in her home gave out, dealing with it independently, which she’d never thought herself capable of, made her feel strong. “I try to look at this part of life as an adventure,” she adds.

Similarly, keeping busy and active helps her keep negative thoughts at bay. Instead of staying home to ruminate on what would have been her anniversary, she traveled to a professional conference out of town, keeping herself productive and growing. One thing that buoys her spirits that never-married singles don’t have? Pictures of her grandchildren.

Being There For Them

Do you have a shidduch for a single in your life?

Sharona wishes you’d go ahead and suggest it. “To me, that’s the biggest honor,” she says, but at the same time she acknowledges that some singles, particularly widows, take offense at unsolicited suggestions. “You have to be cautious,” she says.

Perel agrees that most people welcome suggestions, and are touched to have been thought of. “Feel free to ask, ‘Are you ready to hear a suggestion? Let me know when you are,’” she says. “People often hesitate to suggest a shidduch, out of fear of insulting someone, but it makes people feel good; there are women who haven’t heard a shidduch suggestion in years. It’s a chesed even if it’s not the right one. You can make a disclaimer: ‘I heard of this person, I don’t know if it’s for you, but maybe…?’’” Perel suggests constantly looking out for at least two singles: one man and one woman.

Many times, well-meaning people make the mistake of assuming they can only redt shidduchim similar to a single’s first spouse, but Perel says to discard that notion. “People often go in a different direction for a second marriage. You can think out of the box,” she says. “But at the same time, don’t assume people are so desperate they’ll go out with anyone.”

Case in point is Rivka, whose second husband is the polar opposite of her late first husband. “If you start comparing, you’ll never remarry,” she says. “You need to make a completely fresh start.”

More than any practical assistance you can give the single in your life, dignity is the most priceless gift you can bestow. “Many times I can’t help someone, but I can treat them encouragingly and respectfully,” says Chana Devorah. She sees building up discouraged souls as her most important role as a shadchan. “My mother taught me — never criticize someone for something they can’t change. If you don’t have a shidduch, keep quiet. I like to say, ‘You have a lot of mailos, sorry I can’t think of anyone right now.’ What does it hurt you to say those words?”

When successes are few, what keeps shadchanim going in a bleak and often thankless shidduch landscape?

“I try to remember that it’s not only chesed to bring people together under the chuppah,” Chana Devorah says. “It’s a chesed to bring them one step closer, and to build people up along the way.” While it may be exhilarating to bring a shidduch to a successful conclusion, it’s no less important to redt the shidduch that might turn out to be the next-to-last. “The main thing,” says Chana Devorah, “is that every conversation offers chizuk.”

With caring friends, relatives, and shadchanim providing sensitive support, and an awareness that Hashem spends His days arranging shidduchim, everyone in search of a shidduch can hope for a better future.

Judge and Jury

Being lonely, in shidduchim, and uncertain of the future can be challenging enough, and singles see no need for their difficulties to be compounded by the insensitivity of others.

Favorite topics for bystander conversation seem to include the speed with which a widow is remarrying, speculation about reasons for a divorce, and opinions about how the single is sabotaging himself, all equally hurtful and pointless.

Chana Devorah recalls a particularly egregious incident when she overheard a community member comment, “Did your hear Ira got engaged? His wife’s body is not even cold yet.”

Perhaps the deceased wife had been sick for many years, and actually encouraged her husband to remarry as soon as he could. “Know that it’s not your business, and that you don’t know the circumstances,” she stresses. Whatever wisdom you may have to share, the odds are slim that the single hasn’t considered it herself.

Perel agrees that fear of judgment can often hold back widows who would like to reenter shidduchim. And sometimes, it’s not strangers’ judgment: it’s those closest to them. Ideally, well-adjusted children want their parents to find happiness again, but life is messier than that, and it’s hard to face the possibility of loved ones’ disapproval. “Someone I know finally began to look again, after many years of being alone. When one of her children, who’d been the closest to her late husband, suggested that maybe it was time to move on, she felt free, knowing she had her family’s approval,” relates Perel.

Of course, no one bears the brunt of the blame game like divorcees.

Sharona, who’s been in shidduchim as a divorcee and as a widow, says the experience was vastly different. “It was a different world, after my divorce and as an almanah,” she remembers. “When I was divorced, there was always judgment. It comes with a label. Now, as a widow, there’s no more stigma or guilt. No one can blame me or question my choices.”

While Sharona acknowledges that someone actually pursuing a shidduch does need to carefully investigate circumstances of a divorce, there’s no reason for uninvolved parties to speculate about the goings-on.

Resa relates that after her divorce, even well-meaning friends and acquaintances had opinions to share about her shidduch status. “People want to help, but say very hurtful things,” she recalls. “It’s a universal problem, not limited to this age bracket. But to get back into shidduchim, I had to make a real effort not to let other people’s opinions and judgment hold me back.”

Chana Devorah sums up her hard-won wisdom from her own years in the trenches: “Know that you don’t know. The more you think you know about their situation, the less intelligent you sound.”

(Originally featured in Family First, Issue 629)