Once Upon A Time As a heartbroken freshman in college, I didn’t plan on becoming a matchmaker. But as I struggled to overcome the grief of being blindsided by my high school sweetheart, I realized I couldn’t stay away from love for long. While I had trouble finding it again for myself, that I was a natural wingwoman was obvious to everyone else around me (e. g., if my shy best friend spent two hours doing her hair and makeup only to freeze when the hot guy at Les Deux approached her, I was the first to make conversation on her behalf). It never occurred to me I could turn that into a business, though. Instead, my sights were set on the place where all love stories originate—at least, the epic ones starring Ryan Gosling: Hollywood. I’d known I wanted to be in the film industry since childhood, and even shot a documentary on my high school campus called “Behind the A+,” featuring four seniors competing to be valedictorian. I should have recognized my true calling back then: the characters I was most interested in were the handsome, intellectual jock and brilliant, under-the-radar theater nerd, who had s eparately confessed in interviews that they were crazy about each other. They wound up dating, thanks in part to my encouragement off camera. I never finished that documentary, but I did get into USC film school. I didn’t realize it at the time, but nearly every script I wrote there centered around a love story. While most students were letting off steam at frat parties and spending summers abroad, I was peddling my free labor to whichever talent manager, production company, or studio would have me. I figured if I made the right connections, maybe those love stories could get made some day. Shortly after graduating, I got hired as a production assistant on Family Guy and quickly sensed a trend in the office: it seemed that despite living their professional dreams, nearly every woman over thirty who worked there was single or unhappy in her relationship. What felt like week after week, a particularly adorable and tenacious coworker I admired would come into work crying. She was the whole package, who wanted nothing more than to meet the man of her dreams and start a family, but even though she was putting herself out there regularly, she was still meeting really low-quality men. The few good ones she did meet lacked follow-through. If someone this sweet, fun, and accomplished is having trouble meeting the right guy, I thought, how will the rest of us fare? I was convinced all she needed was an introduction to the right man, and I decided that I could be that connector. From there, my matchmaking side hustle was born. At the start, my introductions were fairly incestuous. After all, I could only set up people I knew. Recruiting strangers made me uncomfortable—my worst nightmare was that some suave, good-looking bachelor I approached at Erewhon would join my database and later go on to do something untoward to one of my friends or trusting clients (a hypothetical later explored in Celine Song’s film Materialists), so I stuck to referrals or people with mutual contacts I felt comfortable enough “inviting.” Absurdly, I named the company LJMatchmaking: “LJ” for “Lady Jaydi,” a cutesy-sounding nickname that inadvertently likened me to a madam (eventually, I was able to r epurpose the “L” to stand for my business partner, Lauren). I started out charging a nominal fee, which only seemed fair given my lack of experience. But while most straight women were willing to pay anything necessary to help navigate a tricky dating scene, the handsome, successful, and down-to-earth men they wanted to meet were sk eptical. In fact, most didn’t
want to pay at all! They believed they could easily score quality dates on their own, and paying someone else for “help” in that d epartment was a bruise to their egos. So I adjusted. Instead of requiring men to pay me, I insisted they pay for their dates (which most were doing already anyway). This system allowed the women to invest in our company, and the men to invest in our women. Before long, I had an enviable group of bachelors at my disposal. For years, I juggled the company on the side while racking up writing credits —starting with Family Guy and Salem, and then eventually developing my own content with producers such as Jennifer Garner and Margot Robbie. (Some curious coworkers knew about my matchmaking side hustle; others would have been shocked to learn I was squeezing in client meetings and scheduling dates between writers’ room sessions.) To my surprise, the two careers started to complement each other, and I was even drawing inspiration from some of my clients for work. These story ideas ranged from the tragic and heartwarming to the aspirational or even comedic, like how one client would only acc ept first dates days 9–15 of her menstrual cycle, when men are scientifically proven more likely to find her attractive, or when another client walked out on his date because her brown hair reminded him of his schizophrenic mother. I was making a good living writing at the time, and decided to run LJM almost like a nonprofit, simply charging so I didn’t incur losses. In addition to complimentary memberships for straight men, I offered the same to LGBTQ+ singles and women over fifty, since I felt I didn’t have a de ep enough database to justify charging them. Fewer than half my clients were actually paying me! Anyone with half a brain for accounting would have quickly realized that this model sucked. (For comparison: in LA, the average rate for matchmaking is ten thousand dollars for eight matches; in NYC it’s fifteen thousand. Some elite ones are even known to charge between a hundred and five hundred thousand. Three Day Rule’s global million-dollar white-glove experience even comes with a custom-designed engagement ring.) But I believed in the art of matchmaking as a means to find love, and wanted it to be accessible to everyone. By prioritizing client success over profit, my patience paid off. I started making more and more successful setups, and was able to build up membership and increase my rates, without compromising the integrity of my mission. This mindset wasn’t only good for my clients; it was good for me. It allowed me to operate in volume—more clients and database members meant more potential matches to make. By 2014, I’d set up a good handful of phenomenal couples, and word was beginning to spread. Then I met Lauren, an unscripted producer and a cofounder of a group called Hollywood Women Executives Stronger Together, aka Hollywood WEST. She wanted to go into matchmaking, and was already aligned with the general practices of my company, such as ke eping all the setups blind. (I’m all about organic first impressions.) She ultimately believed that joining forces with me would be more effective than launching a competitive business of her own, and pitched me her services at a Hollywood WEST function. Almost immediately, I brushed the idea aside. Although my database was increasing, the workload was manageable, and I enjoyed the autonomy of making all the matches myself. I explained to her that my database wasn’t big enough to justify any help. What Lauren heard was: “If you can make my database larger, I’ll need your help.” And that’s precisely what she did. I lost track of the number of referrals she sent my way, and eventually it made sense to collaborate. At first, I suggested she only sit in on meetings with the clients she herself had scouted, but as business progressed, I realized she couldn’t effectively weigh in on their matches because she was unfamiliar with the rest of my database. So, I eventually had her sit in on all intake meetings, and quickly discovered I enjoyed bouncing ideas off her. Our commonalities brought us closer, but our differences, more than anything, made us a great team. Lauren
was the blonde to my brunette, the logical thinker to my bleeding heart, and the Miss Piggy to my Liz Taylor (“two of the most iconic and beautiful Hollywood history figures,” according to Lauren). We were both driven, resourceful, community oriented, generous in our friendships and romantic lives, and enjoyed matching people overall: with roommates, jobs, and, of course, love. A partnership was born. As it turned out, Lauren was more than a great personality fit. She also had the brains for business that I hadn’t quite developed yet. She reminded me we had an LLC to create, tiered membership rates to name and structure, a website to design, and many more tedious but practical st eps on the journey to help quality singles find “the One.” She also k ept my naivete in check. When I first took a stab at matchmaking, I thought it would be simple: match Person A with well-suited Person B and boom. Cue the engagement rings. What I didn’t account for was that just because someone wants love doesn’t mean they’ve done the work necessary to achieve it. Lauren also forced me to admit that some people are harder to set up than others, sometimes for reasons out of their control—and they need to be considered differently when it comes to promises and results. Women over forty who want children, single parents, men with roommates, someone insecure about their body type: most of them will make incredible partners, but when clients treat matchmaking like a trip to a Build-A-Bear workshop (“I’ll take young, busty, outgoing, and blonde, please!”), it can be a tricky medium. So, how could I help everyone while still making a profit? With Lauren’s guidance, I started thinking in terms of mutually beneficial outcomes, and we introduced a waitlist. Rather than take on any dater willing to pay, we would only activate someone’s membership if we felt, ahead of time, that we had enough potential matches for them. This helped maximize our success rate, but more important, it didn’t make anyone feel duped after signing up with us. It also made the overall process that much more rewarding when we were able to successfully match someone from a more challenging demographic—like a latesixties divorcée. Still, I didn’t want to leave the bachelors and bachelorettes on our waitlist hanging, and eventually, I came around to the idea of coaching. Celebrity matchmaker Patti Stanger, introduced through a mutual connection, was the first to suggest I try it when we met at her monochromatic beachside home in Marina del Rey in 2018. She was everything I expected from her public persona and more. Quirky with a flair for the dramatic, she encouraged me to consider date coaching in addition to matchmaking, as you can achieve more immediate success through it (and, d epending on your rates, it can be more lucrative). I already had a primary source of income writing TV on top of my business, and wasn’t sure I wanted to add more to my plate. Besides, I thought, my impostor syndrome at its finest, who am I to tell someone else how to date differently? But as time went on, I heard so much feedback from men and women following their dates—both good and bad—that I started to feel confident in the insights I was gaining from the secondhand experience. At some point, I told myself I was doing a disservice to clients not to intervene and suggest adjustments on their behalf, if only they were willing to listen. I slowly rolled out a coaching arm to my company, and it didn’t take long for me to recognize the joy and fulfillment I received from those sessions. As extensive as my matchmaking database was, I could never guarantee someone’s future husband or wife was in it. But with coaching, I had the opportunity to achieve 100 percent success. Whether I was helping singles up their flirt game, revamp their online dating profile, or adjust their nervous dating habits, I knew I could improve someone’s dating life after just one session. Now, I wasn’t just squeezing in client intake meetings and scheduling dates between writers’ rooms—I was also conducting full-blown date-coaching sessions. I was having trouble figuring out what to focus on. A
podcast Lauren and I were guests on, First Round’s on Me, wound up helping me decide. We were there to talk about dating in Hollywood, and at one point during a rapidfire round of questions, we were asked to participate in a little ol’ game called “Fuck, Marry, or Kill.” I waited for options. “Entertainment industry, dating coaching industry, and Jason Momoa,” the cohost Steve Rossiter threw out playfully (Jason was a callback to an earlier conversation—let’s just say that Lauren has a hall pass). “I’d definitely kill Jason Momoa,” I began somewhat morbidly, without missing a beat, “hook up with entertainment, and marry date coaching.” I caught my breath for what felt like ten seconds. The host quickly moved on, but I was shook by my certainty. I’d found my calling.