Scene One, Take Three “They kicked you out too?” The woman across from me was still grumbling about Pay Pal to one of our colleagues. “Yup,” the colleague r eplied. “These credit card processing companies claim matchmaking is too ‘high risk.’” “I’m telling you, just go with Square, girl. You can build the fees into your pricing.” I shifted in my seat, wondering whose side conversation I’d be able to join naturally. Today was the third time I’d attended an unofficial assembly of dating professionals, and once again, I was left wondering whether it would be worthwhile. The woman who organized the first, May—founder of Two Asian Matchmakers, a company seeking to help men aged 35–65 meet Asian women— created the meetups as a collaboration tool. But in a way, these gatherings— typically held at large tables on restaurant patios or in conference rooms—have become a place for us to vent about industry challenges, size up our competition, and inflate our value enough that our peers will feel comfortable referring hardto-match clients to us. That day, I had one of my own, and I was determined to find a possible bachelor for her. While it’s standard industry practice to tap competitors for referrals, I almost never do it, as my own database is usually extensive enough. But in this case, finding a compatible man for the bachelorette I was working with had proved to be more challenging than usual. Aly, the raven-haired cofounder of Matchmakers in the City (MITC), a premium company I consult for, took a sip of her drink beside me. She had just wrapped another conversation, so I took advantage of the opportunity and pulled up a photo of my client Meera. (While my dates are typically blind setups, when I’m collaborating, pictures are a necessary tool and always k ept confidential.) I shared more about Meera and watched as Aly racked her brain in consideration. Aly’d started her Beverly-Hills-based matchmaking firm years ago with her sister Cristina at the famous pool where the cast of The Hills was discovered. Without producing “evidence” of prior success, she and her sister brazenly approached singles there and asked whether they’d be interested in signing up for their services. The budding entr epreneurs threw out a fee of a few thousand dollars, believing that the costly rate would make their company sound more exclusive. It worked, and their business has grown exponentially since. “I’ve got two perfect guys for her.” Aly smiled. “I’ll have Anthony email you.” Carina, a kindred spirit nearby, wondered if she could see the photo too. As a dating coach, Carina was known for adopting a nurturing approach with her clients, rather than exerting tough love. We’d initially met working for MITC, but forged a professional friendship as we bonded over our own respective operations on the side. Hers, called Atlas, mostly serviced people based in international hot spots such as London and Dubai. With her beautiful curves and understanding eyes, she was instantly disarming to males and females alike. (She was also the most patient dating coach I knew, so if Carina ever declared that a client was “beyond help,” I believed it to be so—at least for the time being.) “She looks sweet,” she commented on Meera’s photo. “I might have someone for her too.” We were about to chat more when a familiar, singsong voice broke the low hum of conversation. “Sorry I’m late!” Melody. Accompanied by her iconic blonde hair extensions and signature skinny jeans and stilettos, she entered the patio, apologizing to everyone for running behind. (Apparently, she’d just left the set of an unscripted TV show she was contributing to.) The fanfare surrounding one of our region’s “It” matchmakers was typical, but I was both envious and annoyed. I felt Melody was more style than
substance, at least when it came to looking out for her clients. Her website touted her as a sought-after matchmaker “to CEOs and celebrities alike,” yet a mutual acquaintance and former coworker of hers confessed to me he’d only ever met one high-profile client in the four years he’d worked for her. Almost immediately, the bombastic blonde had everyone enraptured as she talked up her latest bachelor: a six-foot-five Russian attorney who exuded some of that “strong but toxic masculinity.” She solicited referrals as she continued describing him, and I couldn’t believe how many of my colleagues were jumping at the opportunity. It was as if, through her outgoing nature and magical fairy dust, she was hypnotizing everyone to believe this domineering and problematic guy was actually a “catch.” When the conversation settled down, our fearless leader, May, took out her clipboard and kicked off the introductions. Energy healer and “soulmate connector” Marla went first. The award-winning author and life coach focused on matching affluent men, and always brought positive energy to these gettogethers. I was happy to see her and waved a small hello. Next was Dana, my senior by almost two decades, and our group’s “Real Housewife,” as I liked to call her. Perfectly coiffed and decked out in designer wear at all times, she loved to remind us of the business she was constantly turning down—what we “ladies” needed to do, she insisted, ignoring the fact that we weren’t all ladies (Barry, the lone male dating coach, was listening silently in the corner). She told us that her life changed completely when she stopped taking on the clients she didn’t want to work with. She then went on to brag about a new technology she’d been given access to that would “re volutionize” the industry, she claimed— but when given the opportunity to elaborate, she said she couldn’t reveal any more details without first discussing them with her attorney. When she was done, attention shifted to Kristy from D8 able, who specialized in upping clients’ curb appeal, tackling everything from overall style to their hair and household. As she talked, I made a mental note to try to chat with her later; I knew several clients who could probably benefit from her expertise. Carina went next. And then, it was my turn. “Hi, I’m Jaydi,” I started clearly. “I’m a cofounder of LJMatchmaking, which specializes in setting up people in the entertainment industry. They call me and my business partner the ‘Love Agents of Hollywood.’” I smiled self-consciously. The title, originally bestowed upon us in 2018 by Ari Berkowitz, a TV writer and former client of ours, was a memorable moniker, but I always felt uncomfortable using it to “sell” myself. “Is it true you set up half the cast of SNL?” A redheaded woman I didn’t recognize jumped in as she leaned toward me, curious. “We’ve had some clients who’ve worked there,” I r eplied to her honestly. Her question caught me off guard, as it’s an unspoken rule that everyone’s database is confidential, unless we choose to disclose it. “But if I tell you who, they might have to impersonate you on the show.” The woman gasped, and I couldn’t tell whether she was amused or offended. “I heard you set up Kendall Jenner once,” another piled on. I channeled a stoic expression from my time as a competitive tennis player, back when opponents called me “The Silent Annihilator.” I’d never set up Kendall, but figured there wasn’t any harm in a little bit of intrigue. May suggested the prying woman, Bianca, go next. From her muted, couture pantsuit, it was clear she worked for one of our industry’s giants. While many of us ran smaller boutique agencies, companies like hers, akin to It’s Just Lunch or Tawkify (which had managed to create a presence in every state), claimed to “scale the art of matchmaking”—something that felt contradictory to me. Through their models, numerous matchmakers operate in every city they service —often employees who “look the part” but lack the necessary experience. (Many are even passionate about exploring our field, but I’m passionate about singing in the car, and that doesn’t mean I should be headlining concerts.) In those scenarios, Matchmaker A might get to
know his or her client well, but the strongest match for that person might have been interviewed by Matchmaker B. I admire what these companies have managed to accomplish, but I prefer matchmaking in its purest form. This means personally getting to know every one of my clients and those I match them with. It’s why I mainly operate in one city. Normally I refrain from discussing philosophy with r epresentatives from those companies, to avoid confrontation and to focus more on the ways we could collaborate. But then, I heard it. “Six hundred couples and counting!” Bianca touted her success rate, shrugging as she did so, as if throwing out a number like that was at all normal or realistic. “You’ve introduced six hundred couples who’ve gotten married?” I asked, trying to mask my sk epticism. I was eager for her explanation. “Well...” Bianca backtracked. “At our company, we define ‘success’ by first dates.” “Meaning first dates that lead to relationships?” Melody joined in, equally curious. “Meaning... first dates that lead to second dates.” There it is, I thought. The stats that “trick” unsuspecting singles to invest in their service. I could hardly blame Bianca. After all, she couldn’t help it if that was how her massive company decided to frame her work. Still, if we all went by those metrics, some of our numbers would be in the thousands. Bianca lowered her eyes, embarrassed. I felt bad calling her out, but the comment felt too egregious to let slide. While she was guilty of displaying more naivete than malice, I wondered whether prospective clients were aware of the potential r epercussions that could occur as a result. Most people start a dating company because they’re passionate about helping people find love. Matchmakers can do what computer-generated algorithms cannot: meet countless individuals, face-to-face, and determine who is most worthy of their clients’ time. But once profit enters the equation in this over $4.1 billion industry, the business side of the business can wind up overshadowing the desire to help people. I’ve heard some of my colleagues refer to matchmaking as a “luxury service,” and in some ways it is. But this sentiment likens having a matchmaker to owning a Ferrari or Hermès purse—all seen as “status symbols.” While we indeed are providing a luxury experience, I strive to make finding love “affordable” for everyone, and structure my business model accordingly. Not all profit is evidence of abuse, though. Some business owners who specialize in matching wealthier clientele are phenomenal at their jobs and justified in charging whatever they see fit. After all, the time, effort, and skills required to help procure one of the world’s most important and precious commodities, love, deserves compensation (and has been rewarded for centuries —in Judaism, shadchans are entitled to a brokerage fee by Jewish law, and nayan in India might even receive clothing, food, or farming assistance in exchange for their expertise). But there’s a fine line between being properly compensated for all the vetting, convincing, recruiting, and scheduling required to make meaningful connections happen, and taking advantage of a vulnerable population willing to pay whatever it takes to find their forever partner—something some bad actors have been known to do. When a matchmaker starts off “too big, too soon,” that’s more likely to occur. Before having a sizable database to match people from, some matchmaking company owners jump into hiring employees, opening a brick-and-mortar location, and taking on additional, somewhat unnecessary expenses in order to appear more credible. Then, they pass those costs down to their clients, finding creative ways to justify their ste ep rates. Aside from the actual matchmaking, perks such as photography sessions, wardrobe consultations, mock dates, wingman or wingwoman services, coaching sessions, and more might be offered. The thinking is that even if you don’t
meet your forever person through paying for one of these services, at least you’ll gain perks as a result. There is truth to this logic, but some in our business use perks as a shield to deliver subpar matches. Contractually, a match is usually considered “quality” if two people are on the same page about marriage and kids, and other common deal-breakers in volve religion or politics. But additional important factors such as looks, income, social skills, and more are often considered subjective. In sales meetings, prospective clients are assured their preferences will be honored; however, it’s rare for any one matchmaker to have enough men or women in their database who will meet all of a client’s expectations. (Even if they did, there’s no guarantee those database members are looking for that client back.) So, what happens if a company has three high-quality and realistic contenders for you, but you were promised eight? Where do those five other guaranteed matches come from? Often, matchmakers will turn to their competitors for a standard $250 referral fee (which is a helpful incentive, but less ethical matchmakers will knowingly refer an inferior match simply to collect the referral money). There are also traditional forms of recruitment at singles’ events, country clubs, or white-collar networking functions. There’s even a “matchmaker’s matchmaker”—a firm called “Match Resource”—that companies can hire to help track down other possible leads for you. These options are great, and can sometimes connect you with your future husband or wife, but other times, companies are doing what you could be doing yourself, for free: scanning social media apps, such as Instagram or Linked In, to find dates, even surfing dating apps using manufactured profiles—which can lead to married, mentally unstable, unemployed, and other “undesirable” people populating some databases. Rumor has it that one male matchmaking employee even poses as a “hot girl” on the internet to lure in unsuspecting bachelors. While matchmakers who employ those tactics might get points for creativity, do you really want to shell out thousands of dollars for matches you could find yourself online? If you’re a wealthy professional who doesn’t wish to be “bothered” with the search, the answer might be yes. If you’ve chosen to invest in matchmaking at the expense of other life choices such as freezing your eggs or sending your daughter to private school, possibly not. More virtuous matchmakers will turn down clients attempting to hand over more than 20 percent of their income. Personally, I avoid guaranteeing a minimum number of matches to anyone. I prefer to focus on quality, and instead have clients sign up for a window of time. When a client pays for a guaranteed number of matches, if even one introduction is off base, they might start calculating the “cost” of that match— for instance, “That horrible date just cost me a thousand dollars,” an attitude that causes even the most gifted matchmakers to be more risk averse. By avoiding this trap, I’m more easily able to throw in some “wild card” matches who might be perfect for a client, but outside the realm of what they “requested.” Clients aren’t the only ones paying for matchmaking. If you can’t afford the ste ep rates for such a premium service, database memberships are almost always offered instead (a lesser tier where you aren’t actively being matched, but rather considered as matches for higher-paying clients). This can be a worthwhile investment when the pairing is mutually beneficial, but that isn’t always the case. For example, a male client in his seventies may “request” a gorgeous fortysomething database member who wasn’t previously open to such a wide age gap. A more seasoned matchmaker will level with that client during his sales meeting, letting him know when an ask like that is unrealistic or less likely to be fulfilled, and share reasons for needing to expand the search. But a less experienced matchmaker might make the requested introduction anyway to satisfy the higher-paying member, and that can result in a disappointing experience for the person in the database. Before deciding
whether or not to pay for a database membership, consider whether you know someone who’s already had a good experience with that company. I’d also take geography into consideration. If a firm’s main headquarters are in the South, for example, don’t pay their database fee if you’re in Milwaukee. This may sound like a given, but some companies misr epresent their reach. When possible, try finding a local matchmaker based in your area. After all, as Lisa Purdum, the CEO and founder of Love Inc. Matchmaking, once told me, “Proximity is power.” Finding the right matchmaker for you might be tricky, but investing in that person can change your life. So what are some questions that can help you recognize the good ones? “Are you going to personally be meeting all my potential matches for me?” is a great start. And if not, “Can I meet all the matchmakers on your team weighing in on my membership?” will help. “How large is your database?” is another useful question. There’s currently no way of verifying the number, but gauging the matchmaker’s response might be telling. I’d also want to know how many of my dates a matchmaker anticipates coming from their internal database as opposed to needing to recruit. Recruiting can be a common and worthwhile practice, especially when conducted in creative and thoughtful ways, but if a company employs this tactic, I’d want to know what their typical methods are. Additionally, what happens if you have a dealbreaker or two outside the ones listed in their contract? (For instance: “I’m vegan and won’t date someone who eats meat: I’m morally opposed to it.” I would want to know, ahead of time, if I were sent on a date with a meat-eater and we didn’t hit it off, would my matchmaker still count that as one of my guaranteed introductions?) While they might assure you they’ll do their best to accommodate your preferences, I would also get this response in writing. I’d avoid asking about success rates, because everyone defines “success” differently, and without a governing body to fact-check it, the statistic simply becomes another sales tactic. One company I know claims an 80 percent success rate, which includes clients who get into relationships during their membership period regardless of whether they were introduced to their significant other through the service. They claim their “invaluable coaching” is what helped lead their client toward the right match, and take the credit. This might be true, but prospective clients usually assume the 80 percent refers to the matchmaking arm only. I’m always transparent with my clients if they inquire about success rates, and simply point to the actual number of clients my business partner and I have introduced to their spouses or significant others, voicing my hope to add them to that list. When I first emerged on the scene, some competitors pushed back on my unorthodox business model, concerned it would threaten their bottom line. When their fears failed to materialize, and they realized they could benefit from indirect access to previously unknown singles through my extensive database, they wound up embracing me. Now I’m grateful to finally (and quite literally) have a seat at the table. As I looked around at our group, I noticed that we’d unintentionally seated ourselves by generation: on one side of the table were the OG matchmakers with proven track records; on the other, the younger generation they’d helped mentor (and sometimes fear being r eplaced by). The former, possibly trying to ke ep up and stay relevant, had introduced a good deal of recent industry innovation. The newcomers, meanwhile, seemed more comfortable emulating tried-and-true business models and practices. I sat—both literally and metaphorically—in the middle. “Is it my turn?” Barry had been waiting patiently for the floor. Attention shifted immediately his way—it always did, thanks to an appealing amalgamation of furrowed brow, earnestness, and a British accent. Though he was male, unmarried, and in his late sixties (a rare
combination for a dating coach), he had found success in the industry publishing a book, hosting podcasts, and building a r eputation as an expert in the “divine feminine polarity.” After attending a seminar about how to take a more “masculine approach” to his dating life yielded enormously positive results for his own romantic interactions, he’d decided to forge a new career path and share his findings with the world. What consistently impressed me most, though, was his calmness. Other men in matchmaking tended to be more boisterous and hardlined in their delivery. (I thought of Jimmy, a colleague who was noticeably absent today. A six-foot-four entr epreneur and former host of a reality show, he’d learned the matchmaking trade from his Chicago-based mother, and he once playfully insisted to me that no matchmaker was in it “purely for the love.” I’d admired his self-awareness and ability to entertain, but sensed a whiff of projection.) When Barry was done introducing himself, a side conversation brought up the difficulties of finding more masculine men in Los Angeles—a prevailing theory was that the California variety exuded “bisexual” energy. I hadn’t been listening closely, but Melody put me on the spot: did I agree with her? “Well, the lines are more fluid these days,” I acknowledged. “For some. But I’m not sure lacking alpha energy, or possessing emotional openness, actually makes men ‘bi.’” While her conclusion was a bit misguided, I could see how she’d arrived at it: many men moved to LA to pursue creative or arts-adjacent professions, and often those personalities were not the same ones who were especially outdoorsy or spearheading fantasy football leagues—and it’s harder, sometimes, to match them. I often work with high-powered female clients— studio executives, agents, and others—who make decisions all day and hope for a “man’s man” who will take some of the action and planning off their shoulders at home. “That was the problem in my last relationship,” they complain to me. “I had to do everything.” Their objections aren’t entirely unfounded. Numerous studies have shown an overall slow and constant decline in men’s testosterone levels over the past several decades, indicating there is a possible biological reason for their perceived lack of assertiveness and physical competence. E volutionary social psychologist Dr. Sarah Hill has pointed to the male body’s reaction to women on prolonged birth control pills—known to suppress women’s estrogen levels. Others have speculated a rise in more sedentary lifestyles is a factor, or an increase of men in caregiving roles with more women in the workforce. Academic, author, and podcast host Scott Galloway explains that men these days are provided fewer opportunities to “demonstrate excellence.” I mentioned this to the group, and many of my colleagues nodded in understanding. Barry agreed something needed to be done. “It’s important for men to chase,” he said, “and for women to choose.” Molly, a confident lifestyle influencer with deliberately dyed gray hair, let out a polite but noticeable scoff from the other end of the table. She specialized in setting up singles in nontraditional communities, from sex workers to those who participated in ethical nonmonogamy. (Rumor had it that she was a former adult film star and started her own business after another matchmaking company rejected her as a potential client.) I understood her reaction. After all, she had started her firm in pointed defiance of “the rules,” and had no interest in engaging with them. Once again, I was somewhere in the middle. While I can see some merit in traditional gender dynamics, if I didn’t allow for the gray area, I never would have asked out my husband! Sometimes, I guess, rules are meant to be broken.