November 16, 2018

Modern Jewish Matchmakers Urge Singles to Keep Their Hearts and Minds Open to Love

In Anatevka, fictional young women yearned for a match who, for Papa, should be a scholar and, for Mama, as rich as a king. In 21st-century Los Angeles, matchmaking is different from how it was portrayed in “Fiddler on the Roof,” but is alive and well, bringing single citizens together for serious relationships.

“The best feeling in the world is making a match,” said Jenny Apple of Jenny Apple Matchmaking, who started introducing people in 2013.

“Our clients like that we’re coaches, friends and mentors all rolled up ino one,” said Jessica Fass, of Fass Pass to Love.

Apple, who attended high school in Calabasas, launched her business after years of programming Jewish events. She offers matchmaking, dating consultations and coaching.

Fass, who grew up in Northridge, got into professional matchmaking in 2013 after making three matches on her own, which, according to Jewish legend, earned her a place in the World to Come.

Apple has matched 10 couples who have gotten married or are in long-term relationships. Two of the married couples now have children. Fass, who specializes in international matches, has matched six couples for marriage and two couples who are in a long-term relationship. And through their work, they’ve set up hundreds of first and second dates with local and international singles seeking partners.

Matchmaking isn’t as simple as pairing two single people, Fass and Apple explained in a joint conversation with the Journal. Matchmakers have to get to know their clients really well before they go on a date. Clients fill out a questionnaire, which generally is followed by a personal consultation. (Fass and Apple both focus on matching heterosexual couples; they connect LGBTQ singles to another matchmaker in their network.)

“Singles I’ve met with who are not successful are obsessed with the fantasy.” — Jenny Apple

To understand clients’ goals and outlook, Fass asks where clients see themselves in five years and what they consider a fun date. “Most smart people just say: ‘It doesn’t matter what I’m doing, as long as I’m with good company/the right person.’ That’s the smartest response and the truest in my book,” Fass said.

Fass helps clients plan the date and asks them to write down everything afterward. A few days later, she interviews both parties and provides feedback. Fass noted that attending events with clients helps her see how they interact in person.

Traditionally, making Jewish matches is considered a mitzvah, and only when matches lead to marriage are matchmakers paid. But matchmaking is hard work, and today’s matchmaking professionals want to get paid.

“You orchestrate the date like a producer,” said Fass, who formerly worked in television as an on-set assistant and script manager. “We have to educate people that it’s a service that you pay for up front.”

High-end matchmakers can command fees of $15,000 to $20,000 or even more. Apple and Fass charge about $5,000 for matchmaking services but offer dating coaching and consulting for less.

The matchmakers don’t see dating apps as competition; they’re just part of the dating industry landscape.

“I’m a huge advocate for online dating,” said Apple, who used JDate when she was single and met her husband on JSwipe (now owned by JDate).

Fass echoed Apple’s enthusiasm. “I used to use [JDate] back in the day when there were no apps.” In Israel, she used Tinder and OKCupid, because there, “everyone’s Jewish.” Now, she said, “clients and people I talk to at events say, ‘No one’s on JDate and JDate sucks’ — I believe they [dating apps] all work, you just have to invest time in it. But millennials would all rather be on swipe apps.”

Dating apps make people think “it’s the boyfriend/girlfriend store and there are endless options,” Fass said, but with the apps’ high potential for miscommunication, “we need to just get you on the freaking date.”

Clients should treat app matches like “a hot sales lead,” she added. “If you have time to get on the phone, just talk … you see instant results.” Fass stated a preference for sites like and, where people can share and learn more about each other.

In today’s Jewish matchmaking, dating and partner preferences skewer the layers of traditional community expectations, idealized dating scenarios and contemporary realities like financial stability.

Apple noted that entrepreneurs say they want women who are busy, but not too busy for them. Fass said that beyond “Jewish,” her male clients are looking for someone “attractive to them,” for a “nonjudgmental place to land when they come home,” and for partners with some kind of passion, like volunteering. Some want to be the sole breadwinner others understand that many families need two incomes.

The women Fass has seen are looking for men with a good or at least stable, job, a sense of humor, and someone who’s physically attractive to them, but notes that she’s seen attraction grow for women (but less often for men). Women are often picky about height, Apple added, and although women say “sense of humor” is a priority, matchmakers often have to find out what that really means.

“Remember not to judge height, age or location,” Fass said. “There are only so many Jews in the world who have the same religious level as you. You need to cut some things off your list.  Also, Jews like to eat! Our mothers are the best cooks in the world. So stop judging weight.”

One client of Apple’s would accept only dates with oval-shaped faces. “he was not attracted to a round face. I never heard that before.” Fass had one client who insisted that all of his dates wear dresses. “You can’t force someone to wear a dress,” she said.

“Singles I’ve met with who are not successful are obsessed with the fantasy,” Apple said.

While Apple and Fass are not business partners, they often collaborate on events — their next one is on Feb. 11 — and are fiercely committed to singles.

“Being married isn’t the cure and being single isn’t a disease,” Apple said.

Apple added that singles should take a multipronged approach — attending events, or hosting their own singles gatherings, in addition to hiring a matchmaker. She also notes that singles 40 and older is “a growing niche” that needs more programming.

Fass and Apple believe that there’s a match for everyone, with some caveats.

“We are always trying to make our clients happy but make them understand what is a healthy and happy relationship. It’s OK to be picky about things that you want, but do you know what’s important in a long-term monogamous relationship?” Apple said. Negativity toward a match, sometimes even before a first meeting, can be lethal, she said. “Love’s about giving and not taking.

In terms of a match’s potential, Fass keeps it simple: “Could you see yourself kissing them, and do they make you feel good? Then go for a second date.”

No matchmaker can guarantee love. But, Apple said, “we’re there to give you the best options in the most realistic way possible.”

“We can introduce you to your perfect match,” Apple said, “but you have to be open.”

Navigating the dating game

Technology has revolutionized the dating world, but sometimes it’s better to go old school — especially if you’re on the older side yourself. 

Just ask Judith Gottesman, a former geriatric social worker who’s been running her matchmaking business, ” target=”_blank”>, said she sees a trend where older men tend to go for younger women. However, this scenario can have its own set of drawbacks. 

Older men “much prefer to use a home landline than a cell phone,” she said. “If there’s a 50-year-old man and he’s dating an age-appropriate woman, he’ll pick one night out of the week to sit down, listen to his answering machine, and call her back. If he’s dating a 30-year-old woman who’s texting and on her cell phone all day, she’ll say, ‘Why didn’t he call me all day? Why isn’t he texting?’ ”

Though the dating pool is more limited when singles over the age of 50 look for companions in their age groups, there is additional freedom when it comes to certain areas.

“When having children is not an element of marriage anymore, or you already have them or are not planning to have them, people aren’t hung up on the details they are hung up on when they’re in their 20s,” Salkin said. “Maybe you’ll look at someone with slightly different religious and family backgrounds.”

Those who use matchmakers to navigate the scene say it suddenly becomes much simpler. One Los Angeles resident named Jeff, who is in his 50s, utilized the assistance of Orly Hadida, aka Orly the Matchmaker, a Beverly Hills-based professional who’s been listed in the Guinness World Records as the most expensive matchmaker in the world. He said, “You don’t have to go to bars or do the pickup lines and everything else. She interviewed me, got my background information and did a lot of pre-screening. She tries to match you with somebody you’re looking for and vice versa.” 

Hadida, who is in her mid-50s herself, said that singles over 50 want camaraderie and monogamy, which is what Jeff (who requested that his full name not be used) was seeking.

“When you’re in your 20s and 30s you want to party and travel and don’t take things seriously,” he said. “When you’re in your 50s, you’ve been married and have kids and want companionship.”

Dee Gaines, who has a doctorate in neuropsychology and clinical psychology, and lives in Beverlywood, echoed those sentiments. She started 3InLove, a matchmaking service for older singles that incorporates the Torah and kabbalah’s marital values. 

Dee Gaines started 3InLove, a matchmaking service for older singles.

She said that as people age, they “go through the process of thinking about where they want to put their efforts for the rest of their lives. They ask themselves, ‘What do I want to accomplish with the certain limited time I have?’ They’re interested in settling with a partner they can share a routine with.”

Gottesman added that because health issues come up as they get older, individuals often look for partners who take care of themselves. 

“People want to find someone who is healthy because they lost a spouse who was unhealthy and they don’t want go through that again,” she said. 

Lifestyle compatibility over 50 is about more than health, though. It’s also about money and whether or not people are still up for adventure. 

“Some individuals don’t want a partner who can’t keep up with their lifestyle,” Gottesman said. “If they’re not retired, they want to be with someone who is also not retired. They want someone who has an active, productive life as well. That can be tricky because some people retire early and others never want to retire.”

In their 20s, singles are more flexible. They’re willing to modify how they function and negotiate on certain issues. Jenny Apple, who sets up Jewish couples throughout Southern California, said it’s not as easy to set up those over 50 “because they’re set in their way of life. It’s harder sometimes to get them to appreciate the value of being set up with another quality individual.”

Jenny Apple, California matchmaker

It’s not about being stubborn though. Apple, 31, from the Beverly Hills area, said it’s more about the baggage that comes along with being a certain age. 

“Sometimes it’s understandable. You have children or a sick parent to take care of, and you don’t want to uproot them. That’s a challenge, and a personal life decision, but people … have to weigh the factors,” she said. “They have to say, ‘Is it more important for me to have a partner in life or to be comfortable with my environment?’ ”

Aside from enlisting the help of a matchmaker and setting up an online dating profile, Gottesman recommends that singles who are 50-plus treat dating like they did at any age. That means getting out and mingling.

“If you just stay at home and don’t try to meet anybody, you’re not going to find that he or she will just knock on your door,” she said. “You should go to singles events or volunteer somewhere you care about.” 

Gaines and her partner at 3InLove, Trudy Green, are working on putting together singles events for the older population over the next six months. She said she continues to focus on people of this age for many reasons. 

“The 50-plus community is a wonderful population to work with,” she said. “There is such wisdom and knowledge that comes out of this group.”