Matchmaker, Matchmaker, Find Me An A-Lister: A Celebrity Yenta Finds Me Four Celebrity Soulmates

Matchmaker to the stars Jasmine Diaz demands that I brush my hair and keep an open mind about Ryan Reynolds

Who is Justin Bieber’s doctor? Who tells Emma Roberts her future? Who spray-tans Britney Spears? Welcome to the latest installment of “…To the Stars,” the series that explores the world of celebrity services.

About four minutes into my first conversation with Jasmine Diaz, celebrity matchmaker and "dating strategist," I realize that I have no hobbies, am indistinguishable from the rest of the imminently doomed human horde, and that any illusions I once harbored about the concept of the fixed self are a lie. Diaz has called me in order to "get to know me better" a few days before our official in-person meeting, during which she promises to demonstrate her unparalleled yenta skills by acting like I am one of her famous clients — a Real Housewife maybe, or an NBA player — then matching me with a fellow celebrity of her thoughtful choosing. In theory, she explains, our preliminary conversation will help her create a (pretend) dating profile for me so that she can figure out which famous person would most want to (pretend) fuck (pretend) famous me forever. In practice, our conversation temporarily detaches me from my body.

“So! Tell me about Fun Rachel?” Diaz asks, her voice bubblier than a bong overflowing with Mountain Dew. “What do you do when you're not working? What are you passionate about?”

I feel stirrings of panic, staring at the giant Exorcist promotional candle sent to me unsolicited by Fox that accidentally became the centerpiece of my office décor. "Well, the things I do for my job are the things ... I'm passionate about," I say, pulling up my browser history in hopes it will explain me to myself. ("Five Things To Know About Harry Styles's Rumored Girlfriend," "Brad Pitt tequila," "Rihanna Chinese food.") "Yes," I add confidently, closing all of the tabs and snapping my laptop in half. "I like to read, and watch movies, and talk to people."

"Got it," Diaz replies kindly, like one might to a small child who's just hurled a beach ball 3 feet and is exhausted by the effort. Somehow, though, over the next 10 minutes and with impressive determination, Diaz manages to wrangle a few "defining qualities" out of me: We agree that I enjoy "eating and drinking with my friends"; I am "not athletic" but was "sort of a theater kid in high school"; my worst quality is speaking before I think; I would only date a liberal feminist who never referred to himself as such; and my personal goals include "getting my shit together before I turn 30."

At this last one, Diaz laughs loudly. "To me, you sound like a badass," she says. "You seem like you don't give a fuck." I open my mouth to tell her that I do, in fact, give many fucks — too many, probably — but then consider that our brief but trenchant interaction has indicated the exact opposite. Is it possible that, after only 15 minutes of conversation, Diaz has cut to the heart of all that is wrong with me as a human? Is this — forcing one to confront the wanton emptiness at one's core — how you make celebrities fall in love with other celebrities?

Diaz was pitched to me as an "expert on everything love for over 15 years," a matchmaker who's "on speed dial for many high-profile celebrities, athletes, and business professionals." A week after our phone call, we meet in person at a bland café of my choosing (I give no fucks!), and I ask for more details on her clients, but she tells me she isn't able to elaborate much due to a confidentiality clause. She does name-check The Talk's Sheryl Underwood, VH1's LisaRaye McCoy, a few of Bravo's Real Housewives, and athletes from the NBA, NFL, and WNBA. Diaz attracted these sorts of clients — along with others she refers to as "exclusive" or "highbrow" — after successfully setting up a cast member on VH1's I Want to Work for Diddy, who connected her to an unnamed woman soon to realize her Real Housewives destiny. Diaz also made a point early in her career to cultivate fancy friends. "I focused all my energy on building a network of people — the celebrity stylists, the hair people, all of that," she says. "I made a lot of great friends who were working with big names, and they started referring me to those people."

Diaz is a tall, gorgeous black woman with long dark hair and the elusive chill-but-elegant daytime outfit: bright lipstick, artfully ripped jeans decorated with subtle white hearts, a white top and white blazer, BCBG heels. She's almost intimidatingly sunny and boisterous, with a loud, contagious laugh and the rare smile that is endless yet devoid of mania. By way of contrast, I am wearing jeans and a gray T-shirt, and my hair is insane because I woke up late and didn't have time to wash it. I ask her if she has any tips for me as I "embark" into the world of celebrity dating, and she eyes me, still grinning. "I think you should brush your hair," she says. "And put on a little makeup. And maybe wear a little color."

Diaz, 34, has been very kindly telling people what's wrong with them since high school. "I've always been someone who's very advice-driven," she says. "My parents would say 'opinionated.'" After abruptly moving to Los Angeles from Pennsylvania at the age of 9 for her mother's job, Diaz says she was "very traumatized and depressed," a grade-schooler with no friends who spent years crying alone in her room. At age 13, desperately lonely and near-suicidal, she met a boy, a churchgoing God-fearer who introduced her to Jesus and temporarily turned her into, as she puts it with a loud laugh, a "power Christian." Emboldened by her new faith and her fledgling relationship, Diaz started fixing up her friends as a way to help them sort out their own problems — including, eventually, that same boyfriend, who now has a child with the woman Diaz demanded he date. "Yeah, it was kind of strange," Diaz says, squinting.

Diaz met the man who is now her husband right out of high school, in a chat room full of fellow power Christians. He was a Puerto Rican Marine stationed in Okinawa, Japan, and Diaz was, as she tells it, "a sanctimonious teen going to church all the time and yelling at people because they're not living their life right." The two met in person eight months later, were engaged two months after that, and were married by the time Diaz was 20. Diaz says now she'd never advise her clients to lock it down so young. "But personally, I felt I was ready," she says. "He was and still is a great guy. Honorable, honest, loves hip-hop, woke. And he's still the love of my life."

Eventually, both Diaz and her husband abandoned their stringent power Christianity ("We were so stupid," Diaz says, laughing), settled down in Los Angeles, and had a son. Diaz, who was working in accounting for an entertainment company, kept setting up her friends on the side. "I was the only one married in my group, and I just had nothing but single friends, and I was like, 'Stop asking me if Tad is available!'" she says. After years of figuring out whether Tad was available on a pro bono basis, Diaz quit her day job and started matchmaking full-time. Diaz's first client, who found her website in a random Google search from the U.K., paid Diaz $10,000 to find love (her normal rate is between $5,000 and $10,000, depending on whether the person in question is an "unknown normal everyday person who just wants to meet a nice guy" or a "high-profile client"). Stateside, Diaz began quietly advancing on various Housewives.

Today, Diaz operates her matchmaking business like both a marketing agency and an incidental psychotherapy clinic, coaxing her clients not just through dating scenarios but larger issues like generalized social anxiety and chronic shyness. "I'm kind of a hybrid between a matchmaker and a coach," says Diaz, whose therapist colleague consults on the more sensitive aspects of her work. "I find that a lot of clients don't really have strong foundations. The first couple weeks, it's all about building a strong foundation, then moving into [matchmaking]. With matchmaking I'm fishing for you, with coaching I'm teaching you to fish on your own." Along with three full-time employees, Diaz keeps a database of nearly 400 single people that she updates constantly, and she gets on the phone with 15 or so clients for an hour or more per week, for however many weeks it takes to either teach them to hook a bass or to force-feed them an entire bass. Most of Diaz's clients reach out to her directly, but she finds their matches the way a recruiter might fill an empty position: stalking people on LinkedIn, asking her existing database for referrals, going to networking events. Sometimes, though, she just sees somebody hot. "I see a man walking down the street, and he just looks good, I'll probably approach him," she says.

Diaz tells me several times that her 15-year marriage is one of the reasons she's so qualified to hook up total strangers. "A lot of matchmakers aren't married. Hate to say it, but they aren't," she says. "And I'm also a good communicator — I relate to people, and there are some matchmakers who sort of frown upon you if you're single. You're not a horrible human being if you're single." (But you should put on some color, you're looking a little washed out, no offense.)

It also helps, Diaz says, that she's in an interracial relationship. The majority of her clients are women of color ("If you're black or brown, you know I'm around"), a community she actively pursued early on because she recognized they were underserved by her matchmaking forebears. "A lot of my colleagues, black or white, focus mostly on men. So I work with a lot of women, especially women over 40. I'm dealing with multiple people who matchmakers don't cater to. And then you add black and brown on top of that. I want people to have the love of their lives, regardless of who they are." After nearly two decades, she has a keen eye for determining whether somebody's looking to date "outside their normal box" or is just "trying to sample." "There are some people who are fetish-y about it," she says, "like, 'I want to date a black girl because it's my thing.' Or, 'I only date Asians, or only Latinos.'"

I recall that, during our first phone call, Diaz asked whether I'd be open to dating somebody outside my race; I'd said of course, but Diaz tells me that many of her clients say no. I ask if that bugs her on a personal level. "It doesn't upset me, but I don't understand it," she says. "If you say you're having trouble finding someone, but there's a really awesome person right up the street, that doesn't make sense to me. I'm puzzled. But I respect it."

Which brings us to my celebrity matches, all of whom are technically up the street, possibly even floating around the West Village somewhere, albeit probably somewhere with a reinforced steel gate and a list of people to turn away that will soon include me. Diaz tells me that, after our phone call, she stalked me on social media in an attempt to understand me further. "You seem really funny, and you have a lot of political stuff, so that gave me a lot of perspective," she says. "So this guy has to be very active, but in an unspoken way, like you said." Flattered, I momentarily forget my existential crisis.

"Your first match is Ryan Reynolds," says Diaz, smiling. The crisis returns; I am flooded with cold horror. "He's funny, witty, outgoing, an attractive badass who doesn't give a fuck, like we talked about," says Diaz, unaware of my internal disintegration. "Liberal views, supports gay rights. Says what he thinks and doesn't care who disagrees. A bit of a rebellious side. I think you'd be compatible. Oh, and he married a Jewish girl once!"

All I can think about is Deadpool's Oscar campaign and Blake Lively's "Oakland booty." "I don't think Ryan is for me," I say, from somewhere above my body.

Diaz nods. "Jesse Williams is your second one," she says.

I am yoked back into my physical being. "Yes," I say. "I will."

Diaz laughs. "Extremely attractive. I mean, damn. And his background as a teacher. He has a heart for people, he taught American history and English. He's woke, but doesn't really say it. Also has that rebellious 'I don't care what people think' attitude. He's very passionate about his work and Black Lives Matter. He wrote a piece for CNN." Diaz and I agree that Jesse Williams is a "good option," so Jesse, if you're reading this, call me babe!!!

Diaz's next suggestion, Kendrick Lamar ("very lyrical writing style, and very theatrical videos"), elicits a similar response; Kendrick, don't look at the paragraph above this, and also call me. However, Diaz's last pick is Ed Sheeran, which convinces me that I have lived my entire life incorrectly, am projecting an image of the sort of blissfully fuck-free person who would date an Ed Sheeran, and thusly need to throw away my Exorcist candle and become a power Christian.

Diaz, seeing my face, quickly explains herself. "I thought, you know, he has a good sense of humor, dedicated. But, yeah, he drinks too much," she says. We agree that the drinking is definitely the problem with Ed Sheeran.

A negative of nude Ed Sheeran permanently emblazoned on the backs of my eyelids, I ask Diaz how she'd go about prepping me for my dates with both Kendrick Lamar and Jesse Williams. "I'd say don't swear as much," she says. "In terms of setting you up and actually preparing you for a date, I'd say to any client like you, wear color. I think your personality is fantastic. I think your sense of humor is great. I don't think some people would get your sense of humor. But that's really it. Oh, and a bit more makeup. You can wear pants or a dress on the date. Are you girly?" She looks at me for a long moment. "Wash your hair," she adds.

In only an hour, Diaz has managed to convey to me that I look like an old purse that has been run over, am funny in a way that can be alienating, but also that she loves me anyway. I feel both destroyed and invigorated, and also very famous, because somebody has just spent a really long time explaining me to myself.

Having had enough rapid-fire de facto therapy for the day, I ask Diaz whether she thinks her own disconnected childhood encouraged her to grow up to be somebody who repaired people and then mashed them together like old Barbie dolls for a living. "I don't know that I've ever thought about it that way," she says. "I did this exercise a few weeks ago where somebody asked me what I wanted to be when I grew up. I wanted to be a teacher. It's always been a part of me. And I guess this is a form of teaching — helping people live their best lives, how to be everything they want to be with their love life. I've always had that in me. In some twisty kind of way, growing up with not a lot of friends, moving to a new place, having to fend for yourself, is a lot of what you go through in dating."

As we wrap up our Give No Fucks Café meal, I thank Diaz for her wisdom and comprehensive stalking abilities. I certainly learned quite a lot from our brief time together, including but not limited to the fact that I cannot get away with casual bedhead, and I need to cultivate some kind of interesting hobby, lest I wake up one morning and find myself raising 12 of Ed Sheeran's children on a remote English pond.