Did you hear the one about the actress who caught her boyfriend in bed with another woman?

“Tom!” she cried. “What are you doing?”

“Well, I got a speaking part in the new Spider-Man,” he replied, “and an American Express ad. …”

Mona (not her real name) is a 45-year-old former movie actress who’d had it with fickle Hollywood types. “In my 20s I would only date guys in entertainment: actors, musicians, producers, directors. I needed the excitement. And then you have some experiences, and you get a little wiser.” She dated businessmen and other professionals and fared no better until she started seeing a shrink who made her realize that she was dating the same kind of men and expecting different results. “The men that I was attracted to had narcissistic tendencies,” she says. “These guys were all successful and also very self-focused and pleased with themselves, perhaps a little too much.”

That’s when she sought out a matchmaker. For years any time one of her girlfriends became single, the others would say, “Head up to the San Francisco Bay Area.”

“When I was younger, I probably would have never thought about dating a Silicon Valley guy,” says Mona. But according to Amy Andersen, the San Francisco-based matchmaker who worked with Mona to find the right man, the trend is bigger than her and her girlfriends. “About two and a half years ago, I started getting a ton of pings and inquiries from women living down in Los Angeles trying to find a good, like-minded man,” Andersen says.

As fate, or some algorithm, would have it, the tech world is rife with men with similar complaints. Some are modern masters of the universe. They work for companies and, in some cases, have created or developed products that changed the world and made them and many other people millions. But that does not mean that they can find the right woman Saturday night.

Take Jay, a pseudonym for a San Francisco investment mogul in his early 50s who, like most people in this story, didn’t want to be identified. Jay was married for 17 years before divorcing amicably. He missed the rise of online dating, though he made up for lost time a year after his divorce. “I was mainly immersing myself for the first time in dating sites and found it to be a very significant waste of time,” he says. “I developed empathy for my children in understanding the way these sites are set up to make you addicted to them and keep spinning faces to look for somebody.”

After spinning through a lot of faces, and going on a lot of dates, Jay decided to seek professional help. “I began interviewing a few matchmaking firms—actually I had my assistant do that—and then I got it down to a few, and I met them,” he says. After hearing what he was looking for in a woman, “they all told me you’re not likely to find that person in the San Francisco Bay Area.”

Andersen founded her company, Linx Dating, in part to find women for the men of Silicon Valley, who can be peculiar, to say the least. She grew up in nearby Marin County but got into a serious relationship with a “quintessential Silicon Valley geek,” to whom she is now married. “I witnessed that there was a huge surplus of eligible men and a dearth of women,” she says.

The statistics back her up. According to a recent article in The Washington Post, there are 40 percent more men than women just in Palo Alto (home to SAP, Tesla, and Hewlett-Packard). Bear in mind that in 2018 women held only 20 percent of all jobs in tech.

The line you’ll hear from women about dating in Silicon Valley is: “The odds are good, but the goods are odd.” Chances are that a genius coder or engineer spent his college years in his dorm room hunched over his laptop, while his less talented roommate was practicing pickup lines at parties. Those “odds” who went on to make their fortunes didn’t do it by settling. Talia Goldstein, founder of the L.A.-based matchmaking service Three Day Rule, has paired a number of SoCal women with Silicon Valley men. “The more successful they are, the pickier they get,” she says, “especially those techie guys that maybe didn’t have all the girls in high school. Now they’re really choosy.”

The line you’ll hear from women about dating in Silicon Valley is: “The odds are good, but the goods are odd.”

Jay is wealthy enough to pay for a VIP, customized matchmaking experience. The woman he sought would be beautiful, yes, but older, preferably with kids—and into having more. “I’m looking for truly external and internal beauty,” he says. “And the external beauty factor in the Bay Area doesn’t seem to get divorced. I’ve now talked to five of these firms in depth for the last 20 months, and they all say the same thing, and no one has an explanation. There are just not many. There’s one: my ex. There are coyotes all over her.”

Jay says he has met some beautiful, intelligent, divorced women in the Bay Area. But he has complaints. “They have not taken care of themselves like these women that are in more vanity-oriented cities,” he says. “Mainly skin care, my friend. The sun does bad things. Yes, there are women in great shape in the Bay Area who do all this outdoor activity, but their skin shows their age.”

He says New York and L.A. have the best “supply side of women,” but the pool of eligible bachelorettes in their late 30s to 40s is greater in Los Angeles. “There are enormous numbers of women that either never got married, and now they’re 38 or had long-term relationships that didn’t work out, or they’re divorced,” he says. “And they’ve taken good care of themselves. There’s so many of them that want to get married to a monogamous partner, and the guys in L.A. are not capable of it.”

“The upside of Los Angeles is that arguably the most beautiful people in the country, if not the world, live there,” says Mona. “And then the downside of that is that it’s like a candy store for men.”

Through Andersen, Jay met a woman in Orange County who fit his bill. She owned a fitness business and had two kids in grade school—a plus for him. And if a fit, fun, smart woman of a certain age (presumably with great skin) was a novelty for Jay, you can imagine how he looked to his new girlfriend. “I feel like I’m a unicorn down there,” he says. “Like, you want to get married again? You actually are open to having children?” But after introducing her to his family and touring Europe with her on his yacht, Jay decided that his dream date still had issues she needed to sort out with her ex, and at press time they were on hiatus.

Unlike online dating, matchmakers are expensive. Andersen recruits eligible women to be part of her database and then tries to pair them with the right bachelor. Some women compensate the matchmaker if the pairing is successful, paying a bonus if they get married or engaged. But generally it’s the men who pay.

“People on the VIP level want us to exercise all options and not limit our search to an existing database,” says Andersen. “They want strategic searching, very akin to a professional headhunter looking for the perfect CEO for a tech company.”

Take Jack, a Silicon Valley pioneer in his 40s who worked for one of the biggest names in tech before moving on to help develop another brand-name technology. He also found dating apps a waste of time, though he partly blames himself for that. “I try to think of myself as a very kind person; I like to think of everyone as an amazing person that I could learn stuff from,” he says. “So I wouldn’t meet someone and go, ‘You’re not the right person for me’ and then cut it short. I’d end up spending three hours with them.”

And what wasn’t he finding in Silicon Valley? “A lot of the women were not as feminine as what I was used to in my upbringing,” he says, adding that his parents are “European.” “Even the women that are working in marketing jobs in tech companies, they’re just not as feminine as what I had acquired as a standard.” In a place where even the saleswomen don’t necessarily wear makeup, what’s a boy to do?

Enter Marie, who is in her late 30s and runs a successful entertainment company in L.A. “I never had any problems meeting men or [them] even wanting to pursue more serious relationships with me,” she says. Andersen introduced the couple over the phone more than a year ago; within a few months of meeting, Jack had bought a house in West L.A. not far from Marie. He proposed, and she accepted—but that relationship, too, has gone the way of all flesh. Jack decided he wanted to keep his options open, according to Andersen. “He can’t face the reality that relationships take work,” she says.

Mona was the itinerant partner in her relationship. She met her boyfriend through Andersen a few months ago, and they dated quite chastely. They went on eight dates

before they kissed and waited three months before they slept together. He’s 60, a divorced dad, and a recognizable name in the tech world. “His experience was similar in that, when he went to Andersen, he said, ‘I’m looking for the person I’m going to spend the rest of my life with,’” she says.

The early signs were good. Despite her career as an actress in the world’s vainest city, Mona had resisted the pressure to get Botox. Miraculously her new Silicon Valley boyfriend told her he found the age lines around her eyes “beautiful.” Now they are moving in together, and he even bought them a second home on the beach in Malibu so she can stay close to her L.A. network. They’re talking about a wedding, and while they may not have settled on where to have the ceremony, they want the matchmaker to marry them.

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