How to Win the Date Site Arms Race: Targets Couples

Categories: Dating, Events, Food

Imagining San Francisco from his office in Brooklyn, dating site co-CEO Brian Schechter has no trouble spitting out sunny characterizations. His favorite: The West Coast city is "a playground for romantic experiences" -- a place where a high concentration of jaundiced, single, over-educated but largely dissatisfied adults are bumbling through one of the most vibrant arts and retail corridors in the world, trying to figure out what to do with their disposable income.

If you're a guy running a dating site, that world could easily be your oyster.

If you crush the competition, that is. As Schechter and co-CEO Aaron Schildkrout prepared to launch the latest spinoff of their "modern love company," HowAboutWe, in San Francisco this week, they faced stiff competition from other love connectors. With OkCupid minting new products at a fast clip from its research lab in SOMA, and gay hookup site Grindr controlling such a big swath of the market that it's begun throwing resources at straight people, the dating industry has turned into a veritable arms race. A company like HowAboutWe, which caters to older users (25-34) and retains the musty desktop format alongside its mobile platforms, may have trouble staying ahead.

Schechter says he isn't worried. HowAboutWe's latest product, a city-specific service with curated date packages -- including options for concierge services and ticket giveaways -- is sure to give the company an edge. Designed specifically for couples (and aptly named HowAboutWe for Couple), it's focused on retaining that small, ever-frustrating sliver of the market that churns over periodically, when HowAboutWe makes a viable match. Coupling can be a scourge for dating sites, which, by definition, easily become victim of their own success.

Schechter says he's found a way to combat that problem. "Our mission is to help people fall in love and stay in love," he said in an interview, explaining that the whole gimmick behind HowAboutWe is to suggest fun, cute, dating activities that help people meet offline -- in essence, it's as much an event-planning service as a matchmaker. "We have thousands of couples coming to us and saying, 'Hey, we met on your site. We keep getting these emails with wonderful dating ideas." He and the other staff conceived the datebook as "an extension of their core service."

It's also a way for them to distinguish from the competitor ventures he loves to disparage -- sites like OKCupid's Crazy Blind Date ("I don't know if anyone actually uses that - do you?") and ("I wouldn't call [that one] very cool -- it's almost two decades old and the user experience hasn't changed."). In creating the datebook, HowAboutWe partnered with scads of local businesses and institutions -- including California Academy of Sciences, SoMa StrEat Food Park, Fior d'Italia, Empress of China, Biscuit Benders, etc. -- to develop custom-made dates that include prix fixe dinners, bike rentals, VIP tickets, and other swag.

The calendar will change from month to month, providing myriad ways for HowAboutWe to expand -- and localize -- its curatorial reach. HowAboutWe for Couples will also make Schechter a player in markets that have little to do with dating.

It's a promising revenue model, so long as couples bite -- and Schechter is definitely banking on a large, well-heeled population of paired-off San Franciscans who don't know how to design dates themselves.

He said that couples are actually the industry's best customers. They tend to drift off other dating sites because "[the] product doesn't do anything for them." He paused smugly. "It's kind of incredible that no other dating site has made this move."

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I changed this blog slightly from its original version to reflect that: ) the "datebook" isn't a proper noun; the product is How About We for Couples, 2) that it actually does have a significant userbase accessing the site via mobile platforms, even though this product isn't an app. Also removed sentence that said it allowed Schechter to be a player in social media markets, and clarified that "older" is relative in this case -- meaning ages 28-34.

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