HowAboutWe Opens its Website to Couples Looking for Romantic Ideas

Plenty of singles search online for love these days, but HowAboutWe in Brooklyn sees an opportunity to serve couples who want to try new dating ideas with their current partners. At last week’s New York Tech Meetup, HowAboutWe debuted new features on its website to serve people in relationships—just in time for Valentine’s Day.

Co-founder Aaron Schildkrout said the revamped website represents a broader mission for the company. “Helping first dates to happen is very cool, but what about the second dates?” he asked. “And the third dates and anniversaries?” Paying subscribers to HowAboutWe for Couples get monthly rewards and gift packages such as two-for-one movie tickets through Fandango or catered dinners at home. The website also offers a concierge service for customized date planning for birthdays and other special occasions to help maintain that romantic spark. “There’s falling in love, and then there is being in love,” Schildkrout said.

Founded in 2009, HowAboutWe is not rushing blindly into the embrace of this idea. The site and mobile app started out with a focus on helping singles set up dates for potential romance. Singles on HowAboutWe describe the kind of dates they‘d like to go on. Other users respond to the ideas, and vice versa. It is a different approach compared with singles websites that emphasize profiles first and foremost.

HowAboutWe pitches itself as a tool for getting people together offline instead of chatting endlessly online. However, competition in this niche has increased of late with large players such as and OkCupid, both owned by Internet company IAC in New York, also letting their members propose date ideas for potential matches to respond to. Other matchmakers such as OneStop Singles use the Web to plan singles mixers and speed-dating events. Giving couples a platform for discovering and planning dates with each other may help HowAboutWe further differentiate itself from its rivals.

According to co-founder Brian Schechter, the revamped site was in private beta for the past six months prior to its unveiling at New York Tech Meetup. “We have over 1,000 paying couples using the product and booked over 2,500 dates in January,” he said. HowAboutWe first launched its site in 2010 and is backed by Khosla Ventures, RRE Ventures, ff Venture Capital, and others.

The technology behind the platform continues to evolve, with plans to curate and recommend date ideas based on the day of the week and users’ personal interests. HowAboutWe for Couples already offers discounts of up to 75 percent to paying members for dates planned through the site such as dessert tastings and off-Broadway shows. “You can also gift a date and make it a surprise, which is appropriate for Valentine’s Day,” Schechter said.

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