In the Age of Apps, Does an LA Matchmaker Work?

I’m at Urth Caffé in West Hollywood and I can’t stop fidgeting. I’m waiting to meet someone -- a date! -- for the first time, and I’m hoping that the right arrangement of my hands will lead to everlasting love. Or at least like. Or maybe even like-like. Honestly, I’ll take what I can get.

That said, this isn’t your standard blind date/hook-up app situation: I haven’t met this woman before, I didn’t swipe right on her, and we don’t have any friends in common. She was selected for me. That sounds both impressive and horrifying, but it’s true. She was selected for me by a matchmaker.

It’s not 1957. How did it come to this?

***

I’ve lived in LA, on and off, for about four years now. During most of that time, I’ve been wildly, definitively, stubbornly single. If I’m being honest, “single” has been my natural state for most of my adult life. I think I’m a decent enough fella, but I never seem to make “dating” work. As a Los Angeleno in the modern era, “dating” has mostly revolved around apps. Oh, the apps. Tinder. Bumble. Hinge. It seems like every month there’s a new one. I download them all, do a whole lot of swiping and... nothing. My thumbs get plenty of exercise, but not much more. In the past two years, I’ve had maybe three matches turn into dates. I got stood up once, the other two were each an awkward, stilted date -- then done.

Yet hope swipes eternal.

The offline dating scene hasn't worked any better for me. I've found LA bars to be either total meat markets with music too loud for conversation or dark bars tucked into weird corners of town for hardcore drinkers. I don’t go to the gym enough or do yoga or whatever people do now to meet women during exercise. As a freelance writer, I work alone most of the time, so no chance for co-worker hook-ups.

Los Angeles is a great city and I love it, but, man, it gets so damn lonely sometimes.

***

I randomly met a matchmaker for the matchmaking service Three Day Rule at a Purim party at a synagogue in Bel Air. This was unusual for several reasons:

1) I’m not Jewish.
2) I don’t live in Bel Air.
3) Wait, there are still matchmakers???

I wound up at the event because my friend works at the synagogue and was organizing the party. I like a good party! I like synagogues! I’m not totally sure what Purim is all about (something about escaping bondage), but I was sure I’d like that, too! Why not go? It was a 20s-30s singles event, so there was some of that “let’s meet people” vibe built in. Plus, there was fried chicken, an open bar, a DJ. As the evening wound down, I found myself chatting with Adelle. She complimented me on my glasses (always nice to hear), then immediately asked me if I was single. Which was weird, since I’d just met her perfectly nice husband and he was standing right there.

“I’m not flirting with you,” she said, reading my skeptical look, “I’m a matchmaker.” I might have been less surprised if she was looking to swing.

The mind boggles (at least, my mind boggled). Adelle assured me that, yes, she is a professional matchmaker and, yes, that is indeed an actual job. And yes, everyone sings her the song from Fiddler on the Roof. (She’s surprisingly unfazed by it at this point).

And, more to the point, she wanted to make a match for me. This guy. Chubby. Nerdy. Prone to “dad” jokes. But Adelle saw something else: a funny guy with a quick wit who had found a little knot of friends in the most unlikely places. Maybe, she thought, there was something there. Adelle is in the “lid for every pot” school of love. And she wanted to work with me.

Good luck with that.

***

Back at Urth Caffé, I wait patiently. The café is loud, maybe too loud. I instantly regret choosing it -- I sort of regret all my life choices up until this point. But that’s a normal Tuesday for me. Before the shame spiral really gets spiraling, she walks in, all dressed in blue. Physically, she’s just my type: the right height, the right curves, a killer smile. Maybe this will actually work out. That is, if I don’t screw it up.

I always screw it up.

***

I met with Adelle at a café in Studio City. It looked like a casual coffee between friends, but it was really the first step in the matchmaking process. Eventually, we turned to the task at hand: what was I looking for? And really, what was I looking for? A relationship? A future wife? A “partner in crime,” like every fifth person on Tinder? When you’re trying to date, we kind of skip this step. We think, “Well, I’ll know it when I see it.” But how do you look for it?

Adelle had a standard “intake” interview: a series of questions about me, about my dating history, my likes and dislikes. It was definitely the longest I’d thought about it in specific. Do I like funny women? (I do.) What are my dealbreakers? (Lacking kindness, for sure.) Adelle was great, totally non-judgmental about my quirks and oddities.

We got down to the nitty gritty: how much would all of this cost? TDR has two standard contracts, both of which aren’t exactly chump change: $4,000 for three months, with a minimum of three matches, guaranteed, and $6,000 for six months with a minimum of six. If the first one hits the mark, awesome. If not, you and your matchmaker will keep working until you get it right. If you don’t want to pay anything, you can be added to the TDR database for free, but you’ll only be contacted if a client matches with you. Adelle’s clients are a mix of ages, genders, races. Some are famous (she wouldn’t tell me who, obviously), some aren’t. Some come to her because they’re too busy to find someone on their own. Some, like me, are frustrated by the dating apps and sites, by the meat market bars and false starts. We’re all just wooking pa nub, as the old SNL skit goes, in all da wong places.

Once I’d finished the questionnaire, the matchmaking began. And that meant waiting for matches. It’s not just Adelle’s personal “rolodex” of clients that were in play, but also the wider network of TDR clients, even those working with other matchmakers. Adelle kept me posted, and let me know when she was close to finding a date for me. There were one or two possibilities, but they weren’t quite right. There are a bunch of steps to the process: first, Adelle goes through her list to find possible dates -- people who match my criteria on paper -- and then she actually meets with them in person, where she gets a sense of who they really are, and whether they’d be a good match. It’s all like Goldilocks: this one is too flighty, this one isn’t funny enough. She’s looking for “just right.”

Working with Adelle totally upended how I felt about dating in LA.

Knowing that someone is out there, looking out for you, gives you a kind of swagger. A sense of worth. And anyone who’s been on Tinder for more than three minutes can tell you, it is not great for one’s sense of self-worth. Working with Adelle did the opposite. After every conversation, I felt a little better about myself, about my options. I stood a little taller. It was a nice feeling.

After a few weeks, it happened. Adelle has a match. For me. I have a date.

***

Over the sound of the cappuccino maker and the uptalk and vocal fry of the teenagers at the next table, my date, “B.,” and I get to know each other. She’s charming. Smart, funny. We chat about how we wound up in LA (me from the East Coast, her from NorCal), what we do here (me, freelance writer; her, office manager at a media company). Jokes are made. Stories are swapped. It’s all pretty standard first date stuff.

I ask B. how she wound up with a matchmaker. She tells the same kind of story as mine: LA dating is a tar pit, she was looking for something different, a friend connected her to TDR. We instantly bond, like a couple of war-torn soldiers in a foxhole (a foxhole with lattes, but nonetheless). We’d both love to get out of the game. Isn’t that the goal?

Are there extra matchmaker sparks? Should there be? At the end of the day, it is just a first date, just the start of a thing. Adelle may have gotten us to this point, but after this, it’s all on us.

***

How did Adelle wind up in this seemingly archaic job? Well, like the old Hair Club for Men commercials go, she isn’t just a matchmaker; she’s a former client. Adelle came to Three Day Rule as a customer a few years back. At the time, she was working in corporate marketing and communications. “I thought I was doing everything right,” she says. “Blind dates, online, mixers.” But nothing was really working. A friend suggested TDR to her to get her out of the bubble of single life.

It took her about four months to meet her future husband. Even for her, at first, it didn’t work. Her first match or two weren’t quite the fit. “Sunday night is the toughest night for singles,” Adelle says, “The weekend’s over, the work week is starting and you’re back where you started.” During a Sunday night conversation, Adelle’s matchmaker hit her with an epiphany that really resonated: the only person who really knows what you’re looking for is you. And in order to find it, you have to be honest, not just with other people, but with yourself. You have to let go of some of your preconceived notions and dig deeper into the bigger things you want. So when her matchmaker suggested someone outside of Adelle’s requirements, Adelle took a chance and, boom, met her husband.

Through the process, she’d become close with her matchmaker. When her matchmaker asked her to do some brand marketing for TDR, Adelle was happy to make the leap from the corporate world. Even though she came in to interview for a marketing job, it became clear that she could do more with TDR and, before she knew it, she was matchmaking. Her history in marketing and communications helps, but it’s not like there’s a career path that leads to “matchmaker.” It’s about making the client comfortable, getting them to open up, listening to their needs. People don’t think too much about what they want, so the matchmaker helps them get there.

***

Finally, my conversation with B. winds down. Like a sensible LA dater, I’ve made plans with friends after. So did B. I walk her out. “We should do this again,” I say. “Let’s!” We hug and she walks down Melrose into the sunset. The beginning of something? Maybe. First dates, whether through Tinder or TDR, are always a little awkward. But did this go a little smoother? Did I just think it did, after the whole process with Adelle? I couldn’t answer that question.

While I was working with Adelle, I put away the apps. They’re so tempting, so game-ified. I wanted to see if a real, live person was better than an algorithm and Google Maps. In the end, I got about as many dates out of each, really. (I’m really bad at Tindering.) Of course TDR costs money and the apps are free, but you do often get what you pay for. With Adelle, at least, there was a person, a human being on the journey with me. That counts for a lot.

B. and I tried to schedule a second date, but couldn’t get our schedules lined up. After a few attempts, it was clear that we weren’t quite on the same page. I talked it over with Adelle and she helpfully relayed the message to B. We talked over what about B. was right for me, what didn’t work. (Still not quite funny enough.) I’m back in the Tinder/Bumble-verse now and I’ve had a little success, but I miss Adelle. It’s still pretty lonely out there. After all, isn’t the whole point to find that right someone and get out of the dating pool all together?

Maybe, even these days, it takes the right person to find the right person.

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