On a recent Thursday evening, a crowd of smartly dressed men and women crowded into 1919 Wine & Mixology, the tony Upper Kirby cocktail lounge, for a date with Jamie Rose, Houston’s self-described “millionaire matchmaker.” Lawyers in high heels and backless dresses mingled with oil and gas execs in three-piece suits and expensive haircuts at the French rococo–style bar, or sipped wine in Louis Quinze chairs. Many of them were already clients of Rose Matchmaking, which meant they were spending anywhere from $7,900 to over $15,900 a year to meet other similarly well-heeled Houstonians. (No, you don’t have to be a millionaire to use the service.)
Other guests had come out of curiosity. We sat down with three 40-something women sipping cocktails around a faux-marble, candlelit table. “I’m hoping that her service, if I participated, would put me together with a higher-caliber person than I’m used to dealing with,” said one of the women.
“Yeah, you get the real dregs,” another agreed.
The trio had all tried online dating, none with much success. One, a mathematician, told us that men were turned off by her intelligence. “They all say they want an independent, successful woman, but when they find out I have a nice house, two nice cars, and a PhD, they freak out.”
Finally, the star of the evening, Rose, arrived in a little black dress and 4-inch gold lamé stilettos. One of her clients, Lee, approached to ask for help. He’d been chatting at the bar with a woman in a skin-tight red dress when the woman’s friends showed up. Intimidated by having to talk to so many women, he’d slunk off. “This guy’s an engineer, does MMA, and is a stand-up comic,” Rose later told us. “He shouldn’t be scared of anything, right?” Rose gave Lee a pep talk and told him to go buy the woman a drink.
Rose was born Jamie Rose Villareal in Clear Lake on Valentine’s Day, 1982, and made her first match when she was 16. (Yes, the couple’s still married.) “I loved bringing people together—it was a good, rewarding feeling—but I never thought I’d be able to make money doing it,” she said. After studying business administration at the University of Houston, she took her first job as a management consultant, but the work bored her so she moved into the romance business. For a time, she worked for a national matchmaking service, but decided to hang out her own shingle in 2008.
Today, Rose claims to have over 700 clients ranging in age from 21 to 82. Half of all applicants are rejected, she told us, while the rest fill out a detailed questionnaire that is used to build a biography for her service’s custom software system. She then sends them to a professional photographer, as well as a psychologist.
After that, it’s often time for some tough love. One woman refused to date doctors because her first husband, an MD, had cheated on her. Another had a bad experience with a baseball player and wouldn’t date someone who so much as watched baseball. “I say, ‘Let’s talk about why you think that, because to me that sounds a bit irrational,’” Rose told us. “And then I just kind of stare at them and they feel stupid. A lot of the time it’s just getting people to admit that they’ve got some deep-set issues. If they’re not willing to change and be open, it’s not worth working with them.”
Rose relies on both her instincts and software to determine matches. First dates usually take place on weekends at one of Rose’s recommended restaurants, which include Hugo’s, Del Frisco’s Grille, and Indika. She provides male clients with a list of tips: “Focus on your date.” “Limit your alcohol.” “Getting sexual right away is not advisable.” After the date, Rose phones both parties to check how things went. She claims that 74 percent of her clients end up in successful relationships, which she defines as ones lasting over six months.
On Yelp, the reviews for Rose Matchmaking are about evenly split between effusive (“I came to her in December and have been in a relationship since January!”) and scathing (“Jamie is rude and extremely uncommunicative”; “I spent thousands and received nothing”). Rose said some of the reviews were written by a rival matchmaker and others by “a lady we turned away and went crazy.”
Back at Wine & Mixology, the MMA-loving engineer had located the woman in the red dress on the outdoor patio. “I’m sorry, I’m socially retarded,” we heard the man say. “Can I get you a drink?” The woman asked for Pinot Grigio, and the man looked confused. Fortunately, Rose’s assistant Renee was standing nearby. “It’s a white wine,” she told him.
Later, when we related this story to Rose, she groaned and shook her head. “Oh shit, that’s not good.” Then, when we said we had to be on our way, she tried to lure us back into the bar.
“I actually have this person I think you’d be perfect for!”