A TV Writer's Adventures in Dating Post-Weinstein: The "Office Romance Is Dead"

Matchmaker_Illo - THR - H 2018
Illustration by: Eleanor Taylor

Ari Berkowitz turns to two industry matchmakers who help singles navigate in the #MeToo age: It's "like having an agent for your love life."

Once, on my way to the bathroom in a West Hollywood restaurant, a guy asked if I was his waitress. "Excuse me?" I said, genuinely shocked. "You think I'm pretty enough to be a waitress in L.A.?"

Dating in this town has always been hard. Aside from having the highest concentration of beautiful people on Earth, Hollywood is a small world where being successful often means being social. Most of the people you meet — and date — are in the biz. And that means most of the people you meet — and date — know everyone you've ever met and dated.

But in a post-MeToo world, dating in Hollywood has grown even harder. Let me say this: I am a militant #MeToo/#TimesUp feminist. I think a spotlight on unwanted advances is incredibly positive ... but it does make it harder to navigate the wanted ones.

In November, I went out with a friend-of-a-friend in the industry. He bought me drinks until the bar closed, but after that, he left every move up to me. It wasn't just the "yes-means-yes" standard that I expect, it was like Mad Libs Dating. He presented every decision and left me to fill in the blanks: What should we do now? Where should we go? Even after I got him home, got him another drink, sat him on my couch and intertwined our legs, I still couldn't get him to make a move. Neither one of us knew how to navigate this new post-Weinstein world.

Over the past few months, I've heard of companies in Hollywood instituting open-door policies, or sending female execs into meetings to chaperone powerful men when they meet with women. There are many political and business ramifications, but, honestly, I'm about to spend another Valentine's Day alone, so I'm just gonna focus on the dating ramifications. In Hollywood, the office romance is dead. General meetings will never again bleed into late-night drinks. The blurred lines are focusing. And I'm glad. But Hollywood singles are facing a totally new era of dating.

Enter matchmakers Jaydi Samuels and Lauren Rosenberg. I learned about them the way I learn about everything — in a general meeting. When the female exec I was meeting with casually mentioned she had just started using a matchmaker, I casually mentioned that she had to fucking tell me all the details immediately.

LJMatchmaking, which started three years ago, costs $199 a year for women. Men pay nothing upfront, but are expected to pay for the first date. Members, who are referral only, answer a questionnaire, and then Jaydi, a comedy writer, and Lauren, a reality TV producer, follow up in person, sussing out dealbreakers you didn't know you had. (When they asked if I'd date someone who voted for Trump, I answered: Maybe — if they deeply regretted it now. When they asked if I'd date a guy who was bald, I said: Fuck no. Who knew I was the worst?!) There are no guarantees on how many dates they get you — they just let you know when they find a good match (i.e., a hairy, regretful Republican).

A week after I met them, they emailed me my first match. I got his first name, age, religion, job, and a sentence about his personality and looks. No picture. No way to google him. Jaydi and Lauren asked me: Was I interested in meeting him? Was I free on one of three nights? Yes and yes. Jaydi and Lauren made us a reservation. All I had to do was show up.

My first match was with a guy we'll call "Tom." Tom was 10 years older, a successful writer. We had a nice time drinking margaritas and talking about harassers, and after two hours, he drove me home. But the best part was that afterwards, I didn't hear from him. I heard from my matchmakers. They checked in the next morning: "How did it go?"

It felt amazing — this was like having an agent for your love life. You can leave a staffing meeting thinking everyone loved/hated you, but your agent always gets the real story. I told Jaydi and Lauren that I was interested in seeing Tom again. He wanted to see me, too! There were no Mad Libs about it: We had gone on a clearly defined date and wanted to do it again. Then Tom flaked on me twice in a row, and I pulled the plug. I'm not saying matchmakers fix all your dating problems in Hollywood. Just, like, a dozen of them.

My second match was with "Josh." Josh spent the first hour of our date mansplaining American foreign policy. When he segued to a football player who had been (very mildly) slandered in an article about campus sexual assault, I interjected: "Cry me a fucking river." The next day, I told my matchmakers it was a bad fit. They were surprised — he wanted to see me again.

What?! I got clammy thinking of how I was going to extricate myself. The one time Josh had asked a question about me, I told him about the pilot I was writing and he deftly brought the conversation back to him by listing all the powerful people he knew who could help me. If I offended him now, was there a chance he'd ask those powerful people to hurt my pilot? With a rush of relief, I realized I needn't worry. My love agents would extricate me! I'm holding out hope that by next Valentine's Day, they'll find me someone who thinks I'm smart, funny and — just maybe — pretty enough to be an L.A. waitress.

This story first appeared in the Feb. 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.