Although my matchmaking career was short-lived, I performed it with the hubris of a young sailor who’d seen a map and thought waves were made of paper. I’d signed up for an app called Loop, which lets anyone set up their single friends. Being single myself, I have a lot of them—mostly Jews in their late 20s through late 30s who are anxious to find love and settle down. I figured I could help. I’m a good wingman at a bar.

I scrolled through thousands of dating profiles in various groups, including ones for “fitness freaks,” dog lovers, and Hebrew speakers—the app has been especially popular in Jewish circles. I was searching on behalf of my very tall friend, Jeremy Lefkovich. Tall guys are trendy—so I’ve heard—and I was certain I could find someone for a six-foot seven-inch, funny, outdoorsy, nice Jewish boy with a good job in finance. One girl with wavy hair and a big smile caught my attention. Her profile said she works remotely as a marketing manager, loves to travel, lives an active lifestyle, and is drawn to humorous, adventurous men. 

Jeremy wasn’t sure when I sent him her profile. He was in Denver, she was in New York, and he didn’t want to date long-distance. But I convinced him to give her a chance, so he accepted, then she accepted. It was my first official match. There’s no rabbinic source on this, but it’s a common Jewish saying that facilitating three successful marriages guarantees someone a place in the World to Come. I was easily on my way, I thought.

It’s no secret that young people, particularly young men, are struggling to find partners in the 21st century. A record number of Americans in their forties have never been married. Over 60% of men ages 18 to 29 report being single, compared to 34% for women in that age range, despite more opportunities to date than we have ever had before. Believe me, I’ve been on the apps—those cruel things. Yet none of my soul-crushing efforts and countless forgettable first dates have led to lasting love. I was beginning to think that if the new ways of dating weren’t working, then I should return to the old ways, and I mean really old ways, as an antidote to my dating app fatigue.

I first became interested in this topic after watching the reality series Jewish Matchmaking on Netflix, featuring renowned matchmaker Aleeza Ben Shalom, who sets up a cast ranging from orthodox Jews to Jews who aren’t observant at all. I’d never before considered using a matchmaker. The only person I’d ever known to have found a spouse that way was my great-grandmother, who was married in Germany in the 1930s. While matchmaking is an ancient Jewish tradition going back to biblical times, I’d thought it was just that—antiquated, a practice that those outside of extremely religious circles had left in the past. There’s a stigma associated with it, but that’s been changing. Every one of the matchmakers I asked agreed: they’ve seen a surge in interest in recent years, especially after the 2023 release of Ben Shalom’s show.

“I think that 10 or 15 years ago, using a matchmaker was considered a little bit cringe. It was considered desperate,” Dani Bergman, one of the stars of Jewish Matchmaking, told me. “In the world we live in now, where things are extremely fast-paced—especially with successful people, they don’t have time to be going on dates that aren’t going to work. So when they’re using a matchmaker, they know these dates are sourced, vetted, intentional, and have the potential to be a real match.”

Matchmakers were suddenly coming up in my private conversations too. Nearly all of my single Jewish friends have used one, including my tall friend, Jeremy, and I mean real matchmakers, not just me playing around on Loop. His matchmaker has not only helped him find more likeminded people than he would have on his own, she has also been an invaluable dating coach. “Previously, I would have had this notion that I need to find somebody that is very similar to me or has extremely similar interests or extremely similar religious ideology,” he said. “The way that she frames it is that you’re just limiting yourself in terms of who could be available to you. So, for example, if you were going to say, ‘I’m not going to date a person shorter than six feet tall,’ she would say, ‘Hey, I’m gonna do what you want, and you know best, but if you’re gonna say, I’m not gonna date people with X, Y, and Z criteria, you’re already eliminating 75% of the pool just based off something that may or may not be arbitrary,’ right? And if somebody’s 5’10”, you know, is that something that would really be the demise of that relationship?”

Several startups are getting in on this trend and modernizing it. After her role on Netflix, Bergman, who lives in Miami, launched Club Allenby, a membership-based Jewish social club offering parties with built-in matchmaking elements in cities from Los Angeles to Tel Aviv. Bergman told me the typical attendance at each event ranges from 100 to 1,000 people. “I’ve managed to build a network of over 16,000 Jews all around the world by my social media promotion and my parties,” she said. “I think the matchmaker’s role is to source all the information to find who will fit what you’re looking for, and then you have to basically see for yourself if it’s going to work in terms of chemistry and connection.” A lot of the matchmaking she does herself, manually searching for members who might be a match for other members. But she doesn’t shy away from integrating technology into her events, like software that matches attendees based on their responses to a relationship questionnaire. 

Lox Club, a Jewish dating app, is now offering matchmaking services after hiring another Jewish Matchmaking star, Harmonie Krieger, as a dating coach and matchmaker. Packages run in the thousands of dollars. The waitlist, I was told, is long. “Half of our clients are literally 25. It’s unbelievable,” Krieger said. “It’s funny because the younger generation doesn’t even know what it was like to date when you had to go find somebody without a phone. These apps, which is what everybody is doing now, really don’t lend themselves to true connection.”

That’s also why Lian Zucker, CEO of Loop, founded the app I used to set up my friend Jeremy. “Loop was born from my own personal experience,” Zucker said. “The experience on nearly every single legacy dating app out there is, you swipe on what feels like a bottomless pit of options. People are represented like cards with pretty superficial information, a few photos, and you’re making split second decisions on whether you’re interested or not.” She described it as a game of roulette, where you play and just hope for the best. “It’s an experience that feels random based on volume, without a lot of trust and safety involved. It’s, like, so different from how every single generation before us has met.”

The lack of trust is one of the biggest problems with modern dating. “Dating apps are replete with misrepresentation, catfishing, even fraud,” Zucker said. “Nothing can replace a friend actually vouching for the person. That ensures that it’s honest, right? Like, if I create my Loop profile and connect with a friend and lie about my occupation, where I went to school, or anything else, you know, a friend would be like, WTF. So the mere fact that we are set up as a social network, where people who you know see your profile, has embedded social proof, which kind of eliminates the problem of catfishing.” 

It also removes the ghosting that plagues dating apps. “People are often on their best behavior, because if you set me up, and I ghost or I don’t behave properly, you’ll never set me up again, and you’ll probably judge me for it,” Zucker said. The same goes for traditional matchmakers. “There’s no ghosting because there’s a level of respect that both people have for the matchmaker,” Bergman said.

Last February, I decided it was time I found a matchmaker for myself, so I signed up for a singles event at a Jewish organization to meet some in person. Of the three I talked to, there was one with whom I really hit it off. She’s an orthodox woman, so she asked me not to publish her name, fearing she would be ostracized by her community for appearing in Playboy, but she works with Jews of all different backgrounds, including traditional but not very observant guys like me.

She immediately started sizing me up, asking about my job and lifestyle. She’d done matchmaker training to learn the best compatibility questions, she told me. But she doesn’t like to put too much weight onto questions about preferences. “I’ve actually found that people don’t know their preferences,” she said. “Men, especially, I feel like, are hesitant—especially if they have physical preferences, looks and so forth—to verbalize them, either because they don’t know or they feel embarrassed about the kind of look they’re attracted to.”

Instead, she wanted to get straight to sending me profiles just to see who I’d be interested in or not. A little trial and error, she thinks, is the best way to figure out what kind of partner someone is really looking for.

The database she uses, through a site called JMatchmaking, is accessible only by approved matchmakers and has profiles of tens of thousands of Jewish singles located around the world. To be included, I uploaded a few pictures of myself and filled out a resume by answering basic questions—education, height, favorite music—and some specifically Jewish questions—Shabbat observance, synagogue attendance, whether I’m the grandchild of Holocaust survivors. 

While some matchmakers are paid, many, including mine, are volunteers, though Jewish law requires me to give a gift to anyone who makes a match that results in my marriage. The standard today is around $3,000. A rabbi I met at the singles event suggested putting the money in an envelope and setting it aside to shift my mindset from “maybe it’ll happen, maybe it won’t” to “fully expecting it to happen.” That little difference in perspective can be the change someone needs to start dating with intention.

What really appealed to me about working with a matchmaker was the tether she could be between me and reality, someone to hold me accountable in spending my time dating only who’s good for me. I’ll admit, I haven’t been the most intentional in the past. I’ve been on plenty of dates with people who posed compatibility issues, but they were cute, smart, or fun, so I wanted to give them a chance. It’s not always practical to be so open-minded though. My matchmaker told me about another client of hers, a secular man, who asked about a girl he’d happened to see at a Jewish event. “I told him she’s more orthodox. I know she’s going to want to keep kosher, at least at home. And the bigger deal,” my matchmaker continued, “she’s not having sex before marriage.” He thought about it, and to my matchmaker’s surprise, he said, even though it wasn’t his preference, it wasn’t a dealbreaker. 

“As a matchmaker, first my job is to help you figure out who you are and what you want,” she said. “I tell people, truly, I don’t judge you. I’m not here to judge you. I’m just trying to figure out who you are. As we started having these conversations, I actually said to the guy, ‘I think you’re amazing. I think you’re this and that. I’m not sure you’re orthodox and that you should be dating orthodox girls.’ And then I offered him a more traditional girl, but not fully orthodox, and they’re actually dating very seriously.”

Last year, 32-year-old Inna Binyatova moved from New York to Colorado and decided she was ready to go all-in on dating. She joined the apps, showed up to as many events as she could to meet men in person, and signed on with a local matchmaker. “I also had the intention to exclusively date Jewish, which was not the case in the past,” she told me. “I definitely, like, limited my options just to Jewish men who are also dating intentionally, dating for marriage, and have the same priorities and values in life that I do.” 

Right away, she felt a bond forming with her matchmaker—a volunteer one. “She was very real, she seemed very blunt. She didn’t beat around the bush. She asked good questions, deep, thought-provoking questions, and it felt very easy speaking to her,” Binyatova said. “I made it my business to make sure she knows who I am, what I’m like, what my personality is like, what I do. I definitely feel the pressure of time. I’m not here to waste it.” She continued, “It often felt like I was speaking to just, like, a girlfriend, who happens to have, like, a database of men.”

Her matchmaker was also willing to push her outside of her comfort zone, trying to see where Binyatova might be a little flexible with her preferences, particularly on levels of observance. Binyatova isn’t very religious, but, she said, “If they need to observe their religion a little bit more deeply than I do, I’m totally fine with that if we align on how to raise our kids.” But on certain things she wouldn’t budge. Like when her matchmaker tried to set her up with someone in Alaska. “This guy is, like, obsessed with Alaska,” she said. “But I will not be going to Alaska.”

Now, Binyatova is dating a rabbi from the midwest. Her matchmaker not only found him for her, she also tracked down one of his family members and vetted him. It wasn’t a match Binyatova was expecting. “He has kids from a previous marriage, which, initially, I was like, absolutely not. I want to have my own kids, and I think that’s a really challenging thing to navigate,” she said. But her matchmaker, knowing how much Binyatova loves children, persuaded her. “She was like, ‘just give it a shot, just see where it goes.’ And it’s been the greatest thing ever.”

I regret to report that Jeremy did not marry the girl. He did go on a date with her in New York, though it didn’t go any further.  I should have known, as the Talmud says, making a match is as difficult as splitting the sea. I retired from my own matchmaking career soon after. Then, something interesting happened. Jeremy and some of my other friends started sending me matches on Loop. I may not have found them their true loves, but I guess my effort had made them want to help me too.

Zucker told me there’s a lot of reciprocity on the app. “If you set someone up, they’re much more likely to set you up,” she said, which I thought was nice. It’s good to have people looking out for you on your dating journey, like a matchmaker should. (Just as I was finishing this story, my matchmaker texted me with a new match in mind.)

You don’t have to be Jewish to date like this, but you can learn from the Jewish ways. Ben Shalom wrote her book, Matchmaker Matchmaker, as a guide to better dating practices for everyone who’s marriage-minded, regardless of their culture or religion. She believes anyone can make a match. And it’s true. Loop recently had its first non-Jewish engagement, and Zucker hopes to see more non-Jews joining the app soon.

“In the last decade, dating kind of became this thing where you fend for yourself,” Zucker said. “I mean, think about when people use dating apps, like, when they’re alone on the toilet, when they’re in bed late at night.” It makes no sense for these important decisions—choices that could change the course of your life—to happen in such a solitary way.