Photo by Emily RAchel Hildebrand

HowAboutWe Wants to Plan Your Next Date

How one online dating site is trying to expand beyond singles

Over the past two decades, online dating has evolved from a suspect (and slightly sketchy) way of connecting with strangers to a routine part of many singles’ dating routines. As the pool of online daters has exploded, so have the number of sites designed to serve them. But rarely mentioned in discussions of online dating is one nasty secret known to everyone in the business: the more successful dating sites are at their stated goal of pairing users with suitable partners, the more rapidly they lose their userbase — and with them, their subscription fees. An online dating site that’s highly successful at helping singles find “the one” won’t be keeping those singles, or their money, around for long. And since doing a bad job at your stated goal isn’t really good business, sites have been trying to come up with innovative ways to keep the income coming in long after their users have happily coupled off.

Different sites have had different strategies. Some try to expand beyond dating to promote their utility in the more evergreen pastime of finding friends. OkCupid (which, unlike most of its competitors, largely eschews subscription fees and derives income from advertising) has added offline events to its roster of services, encouraging users to buy tickets to exclusive outings and meet other OkCupid users while learning about beer, playing board games, or eating Chinatown’s smelliest foods (just to name a few possibilities). But HowAboutWe may have found the most interesting strategy of all: rather than putting the emphasis on meeting, they’ve chosen to focus on dating. And whether those dates are a couple’s first, or their fiftieth, HowAboutWe hopes to help make them memorable.

In its original incarnation, HowAboutWe offered a unique twist on online dating. Rather than encouraging users to partner off based on shared musical tastes or political views, the site created a structure in which users were encouraged to choose one another based on a shared interest in offline activities. The site’s single users are prompted to finish the phrase “How about we…” with an idea for a date; other users who find that suggestion compelling can contact them and arrange to make the theoretical date a reality.

HowAboutWe’s focus on crafting memorable offline dates was novel enough to get it media attention and successful enough to sustain the interest of users. According to the sites’ founders, users continued to check out the site to peruse the date ideas even after they’d happily paired off — and with that revelation, a whole new business strategy was born.

Launched in 2013 in New York and San Francisco, HowAboutWe for Couples is part concierge service and part Groupon. Sign up for the site, and you and your partner will start to receive daily offers for discounted dates around your city: dinners for two at fabulous restaurants, outings to movies and museums, access to new and noteworthy bars. If the suggested dates are uninspiring, there’s an option to go more custom: HowAboutWe offers members access to a special concierge service, where “date curators” plan special occasions for couples, creating an evening where every detail has been accounted for.

So far, the formula seems to be working: HowAboutWe reports numerous happy users (though not all of them are couples using the site together — quite a few are partners who use the site in secret and pass off HowAboutWe’s hard work as their own). The company chalks the success up to a new found niche: as Americans get busier, they have less time to spend with their partners, and less energy to plan quality dates; HowAboutWe acts as both a time saver and an experience enhancer.

But the lessons of HowAboutWe for Couples seem to expand beyond the specifics of the site itself. In switching their focus from meeting to dating, HowAboutWe has shifted its goal from helping users optimize a one time experience (the first date) to optimizing a lifetime of experiences (all dates). The better a job HowAboutWe does, the more likely they are to retain their userbase. And that’s a paradigm shift that has the ability to turn the whole of online dating — and, perhaps, other industries as well — completely on its head.

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