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    When Tinder and Cupid fail, matchmakers find their niche

    “I tell people I’m kind of like a headhunter for their love life,” says Jill Vandor, a matchmaker at Boston-based matchmaking service LunchDates.
    Jonathan Wiggs/Globe Staff
    “I tell people I’m kind of like a headhunter for their love life,” says Jill Vandor, a matchmaker at Boston-based matchmaking service LunchDates.

    In an ever-busier and more harried world, Americans have shown a willingness to outsource an expanding list of life tasks — laundry, dog-walking, grocery-shopping.

    And also, apparently, the eternal search for love.

    Thanks in no small part to growing frustrations with the hassles of online dating, a niche — and seemingly outdated — occupation has quietly managed to claim a piece of the increasingly digitized dating market: the modern-day matchmaker.


    “If you’ve ever used dating apps, you know that it can really be like a full-time job,” says Hannah Orenstein, whose experience as a matchmaker in New York City serves as the inspiration for her upcoming novel, “Playing With Matches.”

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    “If you live in a big city, you can pay someone to do your laundry, hire a personal trainer to help you work out. And you can hire someone to help you date.”

    As online dating’s popularity has skyrocketed in recent years — use among young adults (who admitted it) nearly tripled between 2013 and 2015, according to the Pew Research Center — it’s also developed into something of a Wild West, say those who’ve participated, rife with annoyances and potential pitfalls.

    Aside from the general concerns that come with meeting strangers online, frustration abounds, from hours spent swiping left or right to online conversations that never evolve into face-to-face meet-ups.

    “The amount of time I spent was infinite relative to the number of dates I’d go on,” says one middle-aged man in the Boston area, who tried online dating after his divorce, and before eventually turning to a matchmaker. “A big part of the time you spend on those sites is sort of weeding out really low-quality dates, people that clearly aren’t going to match up.”


    What matchmakers offer, then, is convenience — handling everything from identifying dates to vetting dates to scheduling where and when two people will meet.

    “I tell people I’m kind of like a headhunter for their love life,” says Jill Vandor, a longtime matchmaker at Boston-based LunchDates who says that firm has seen an influx of clients looking for a more personal touch. “All you’ve got to do is get dressed and show up.”

    And unlike online dating, they never arrive at a date surprised by who’s sitting across from them.

    Before eventually hiring a matchmaker, one local woman remembers arriving at a first date with someone whose online photos showed a man of around 50. Reality proved him to be closer to 70.

    With a matchmaker, she says, “if they say they are introducing me to a 58-year-old attorney with three kids who lives in Arlington, that’s who I’m meeting.”


    In a lot of ways, the job is the same as it’s always been. It can be pricey, ranging from a few hundred dollars for some services to tens of thousands for others. And it typically trends older, with many clients around middle-age.

    But it’s also evolved considerably from the days of the old-fashioned Yente from “Fiddler on the Roof.”

    While intuition and gut feelings certainly help, they say, today’s matchmakers have an array of tools at their disposal designed to match their clients with Prince (or Princess) Charming. There are databases to be searched. They scour local meet-ups, yoga classes, even subway cars in search of potential matches.

    In a modern-day twist, some even hit the dating apps so their clients don’t have to; during her time as a matchmaker with Tawkify, Orenstein would scour the online dating world in search of promising matches for clients.

    Many matchmakers, too, have become de facto dating coaches.

    After a date, they’ll interview both parties about how it went, then spend time with their client going over behaviors he or she might improve. If a man spends too much time talking about an ex, he may hear about it the next day.

    Matchmaking may rank among the oldest professions, but it hasn’t always enjoyed vast social acceptance. Before the stigma of dating assistance dissipated in recent years, Vandor remembers attending weddings for clients who didn’t want anyone to know how they’d found one another. “I’d be sitting at the misfits table,” she says. “And I had my little story about how I knew this person.”

    Today, though, some online dating sites are toying with options that bring a little of the matchmaker spirit to the process. Apps such as Wingman are designed solely for allowing users to suggest dating candidates for their friends, while more traditional apps, including Tinder, now feature a “recommend-for-a-friend” option.

    And while it’s true that the matchmaking industry probably isn’t going to supplant online dating any time soon — in a 2009 national survey of couples, Stanford sociology professor Michael J. Rosenfeld found that only 1.5 percent of couples met through a traditional matchmaking service — some say that there’s plenty of room for everyone in an ever-evolving dating world.

    “Dating is difficult for everybody,” says Orenstein. “And people are always going to look for alternatives to make it easier.”

    Dugan Arnett can be reached at Follow him on Twitter @duganarnett.