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Dating Websites Get Sick of Flings and Start Wooing Couples

Dating Websites Get Sick of Flings and Start Wooing Couples

Photograph by David Cleveland/Corbis

Dating websites don’t want to pressure their users, but it’s time to discuss where this is all going. Don’t get them wrong, it’s been fun arranging algorithmic matches and occasionally getting lucky. But the average user spends about seven to nine months with a dating website before disappearing, and brands like and HowAboutWe are looking for more of a commitment.

It’s the paradox of the online-dating industry: Success and customer retention are pretty much incompatible. The antidote sounds kind of like, well, dating. Use the singles side of the business to attract people, and then pitch the happily paired-off users on a long-term relationship with the website by offering services for couples.

The furthest along this path is HowAboutWe, which launched in New York in 2010. A year ago the company started offering HowAboutWe for Couples, a concierge service suggesting activities for people in relationships. At first the company’s founders were a bit concerned that going after couples would be like inviting their single users to a dinner party hosted by married friends, boring the bachelors and bachelorettes to tears while reminding them of their loneliness. But HowAboutWe tried it anyway, and the company claims it’s seen a boost in customer conversions because of the service.

“The presence of this second product helps to alleviate the taboo and have people focus on the goal of falling in love,” says Aaron Schildkrout, HowAboutWe’s co-founder and chief executive officer.

The main value of the couples service would seem to be a way to keep people around after users exit the dating scene, but HowAboutWe says that only 12 percent of their coupled-up users are alumni of the dating service. Like all dating sites, it’s fond of curious yet useless metrics, such as the claim that it has helped couples spend more than 56,739 hours of quality time together. In the last three years, HowAboutWe has expanded its couples service to Los Angeles—its fifth market—and added a last-minute-dates service in New York.

IAC (IACI), the parent company of well-known dating services, OKCupid, and Tinder, has also been looking for a solution to “lifecycle management” for some time. “A lot of people think, ‘Oh, dating sites, you guys should start a wedding business,’” says Sam Yagan, CEO of IAC’s Match Group. “Of course, the problem there is that you leave Match after you go on the fourth date with someone, and it’s years before you get married. We lose our right to communicate with them.” Yagan launched his company’s couples website, Delightful, in October, with a companion app released last month.

Trying to snare the attention of activity-minded couples puts Delightful and HowAboutWe in closer competition with daily deals sites like Groupon. This could be a huge opportunity: HowAboutWe claims that people in relationships spent $70 billion last year doing things like going out to dinner and trying BYOB painting classes. Schildkrout says the company rejected the daily deal model of offering discounts and asking merchants to share revenue; fancier dating destinations wanted no part of it.

Delightful, which has about a dozen employees in the Bay Area, is built around access to date planners. It’s hired people with experience as tour guides, restaurateurs, and hotel concierges and helps secure last-minute reservations for its members, who pay $12 a month. The idea is that members will use it to plan dates with people they’ve found on Match’s dating sites, or find things to do with their steadies. Delightful is currently available only in San Francisco.

Although Yagan is investing in a service for couples, he says the paradox at the heart of the dating-service business model has been overhyped. Yes, people stop using the sites when they think they’ve found their soulmate, but most of the time true love doesn’t last. When former users acknowledge that their relationships have gone sour, will be waiting to welcome them back.

Brustein is a writer for in New York.

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