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Dating Gets Outsourced

The incognito date-planning service that gives you all the credit. 

Image by Ashley Batz

Instant matchmakers like Tinder are skyrocketing in popularity, old-fashioned online dating has long gone mainstream, and app-happy San Franciscans have more dates lined up than ever. But not many of these rendezvous are up to par, says Melissa Edwards, 29, a marketing professional at a social gaming company who goes on two to three dates a week.

The North Beach resident sees men repeat the same mistakes. “Guys don’t plan or think ahead. They’ll show up to a new restaurant without a reservation or take you somewhere generic like the Tipsy Pig,” she says. “Or they’ll just ask, ‘What do you wanna to do?’” She often finds herself advising the engineers she works with on where to woo their dates. “They’re so grateful for the guidance. They have no clue.”

Edwards and her best friend Jessica Vasquez, 27, who works in digital advertising and moved from L.A. to the Marina two years ago, saw opportunity and launched Datebook, a discreet date-planning service designed to set men up for success, in April 2013. The pair first met as colleagues and earned a reputation as date experts among their friends and co-workers.

Edwards and Vasquez have billed their new business as “easy, personal, and Marina girl approved,” nodding to a potential target demographic. They secretly create itineraries—handling restaurant reservations, ordering flowers, hiring cars, reserving tickets, booking hotels, and shopping for gifts—and let their clients take all the credit. The duo sets high standards, making menu suggestions and prepping clients with interesting facts about the venues.

Prices range from about $40 for a single night out to $200 for a monthly membership that includes unlimited trysts. The agendas, which can be designed for a first encounter or an anniversary, are customized after an initial consultation that gleans a sense of the customer’s personality and interests. “We get to know them and ask about the girl—how they met,” says Edwards. “But we don’t judge or ask questions if they’re playing the field and taking out different women.”

What kind of guys shell out cash for a date concierge? So far Datebook has attracted a growing clientele of busy Financial District types and what the founders describe as “kind of dorky tech guys,” ages 25 to 40. Vasquez likens the appeal of the site to services such as Uber and ZeroCater, “where the car or the food shows up and everything is taken care of.”

However, some members of Datebook’s anticipated market are skeptical about the covert approach. “It seems dishonest since it’s outsourcing the personal creativity of dating,” says Simon Levy, a 27-year-old Google engineer.

But Shane Hubbell, 26, an investment banker in Palo Alto, is keen on the Datebook concept. “When you plan a date, you want to look like a boss—you know, like have random facts to impress the chick about why you chose this place,” he says. He even has an idea for improvement: “If they put every detail into Google Calendar invites, so I could feel like I'm a secret agent following instructions via cell phone, that'd be cool too.”

At the end of the day, Edwards and Vasquez see themselves as reviving courtship. “It’s refreshing to have everything planned out—to be picked up in a car instead of being told to meet at a street corner,” Vasquez says.

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