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Finding and keeping loyal customers is a core business challenge that trips up many young companies. With so much competition, consumers have endless options to choose from.

Brian Schechter and Aaron Schildkrout, the founders of dating website HowAboutWe, say that to keep customers happy and run a successful business, you need to find and fix a problem. Then you need to never stop fixing it, which they found out the hard way.

HowAboutWe, launched in 2010, has quickly grown to 1.5 million users and more than 100,000 dates posted monthly on its site. Unlike traditional dating sites built on posting and viewing profiles, HowAboutWe's users post and view date ideas, such as "how about we... go kayaking in the Hudson River." Those who are interested in specific dates can then contact the person and, potentially, follow through on meeting up. The focus of online dating is then placed on the date idea and experience itself rather than browsing through users' profiles, say the founders.

Schechter and Schildkrout, who are friends from childhood and former high-school teachers, launched HowAboutWe because they wanted to solve a "deep human problem" that wasn't being addressed: the dating industry doesn't push people to meet offline and share experiences to build their relationships. 

"There were a bunch of problems with the existing online dating sites," Schildkrout tells Business Insider. "This is a culture of endless profile browsing, winking, and long-extended online conversations that even if they led to a date at any point, it would be this sort of stale coffee shop date."

It turns out, their theory was right, but it almost worked too well. Last year, the founders realized they had become so successful at making matches that they were losing their happiest customers.

"We've connected many thousands of people who are now in relationships and have gotten married," says Schildkrout. "Somebody emailed us the other day with a picture of a baby they have; they met on HowAboutWe. The problem is, once they connect and they're in a relationship, they have no use for our product."

Realizing that they were losing the successful matches, Schechter and Schildkrout decided to come up with a product for these couples. That was the beginning of HowAboutWe for Couples, which aims to curate, book, and set up creative dates for couples. The service launched in New York City last year, followed by San Francisco a few months later. The founders say they plan to expand to other cities soon. So far, the couples service has 130,000 users signed up, and one account is typically shared by two people.

If the modern dating problem for singles is too much online browsing, Schildkrout says the modern love problem for couples is giving up on relationships too easily. Couples stop trying to make their relationships interesting because they get too comfortable, he says.

HowAboutWe for Couples was created to avoid the endless cycle of Netflix and Chinese food that many couples find themselves in. The site's couple service offers discounted dates, which include eating the smelliest foods in Chinatown or participating in a dumpling-making class. Members can sign up, pay, and reserve their spot through the site. Then all they need to do is show up.

"We have an editorial team that's really passionate about great dates, finding places people want to go, and creating the kind of activities that really provide for an opportunity to connect," Schechter tells us.

Members can upgrade their experience by using the special concierge service, which costs $18 monthly, where your dates are planned down to the tiniest detail ahead of time, such as having flowers delivered or door-to-door car service on your date night.

"We're curating the dates for our couple members. The concept is still the same, but we've become the experts," says Schildkrout. "This really filled out the whole vision of the company, which isn't only about helping people fall in love, but also about helping people stay in love."

There's another benefit to having so many creative date ideas filter through the singles service: the founders say that they're able to see trends before the rest of the world knows what's happening. "When we first launched, we saw the beginning of the lobster roll craze coming, and about a year and half ago, we saw when donuts were becoming mainstream over cupcakes," Schechter tells us.

Those trends give Schechter and Schildkrout a glimpse into what their customers are most interested in and how to give them what they want. This is most helpful when coming up with ideas to help people fall — and stay — in love.

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