Not Your Grandma's Matchmaker

I’m very excited to share my first piece for Playboy. The recently revived magazine gave me the opportunity to write about a topic I’ve been quietly obsessed with for the past year: Jewish matchmaking. Even if you’re not Jewish, even if you’re not single but know someone who is, there’s a lot to learn from this ancient Jewish tradition. You can read a short excerpt below and the rest at Playboy.com.

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.”

Continue reading at Playboy.com