When Curtis Harris got divorced, he suddenly found himself on a lot of dating sites. He tried Match.com, eHarmony, OkCupid and others, but it was still hard to meet people. And what’s more, beyond the difficulty of finding someone interesting with whom you are compatible, there was the cost.

Dating is an expensive endeavor, especially if you’re doing a lot of it. This survey estimated that the average American single spends around $20,000 over the course of his or her dating life. Harris saw a problem here. A problem both personal and universal, and a problem he could solve.

So Harris founded Cool With It, a dating site with a unique twist.

Cool With It is free to use and partners with local restaurants and bars to give date-night deals to people who meet on the site. In this way it’s sort of like the D.C. startup Spotluck with an added dating component — for the partner restaurants it provides extra marketing and a kind of yield management (restaurants can offer bigger incentives on typically slow days like Tuesdays) and for the user it provides savings.

“People expect incentives,” Harris said. The deals also, potentially, help take the pressure off where to go and what to do on a date. Harris agrees: “It makes the date a little more easy going.”

Cool With It also utilizes its own pseudo-monetary system within the site to cut down on spam and superfluous messages. Want to connect with someone? Message them? Ask them on a date? You’ve got to use “credits” to do that, and you’d better use them wisely. Every user gets 20 credits per month, but can earn more by taking brand surveys or reviewing partner restaurants — another way Cool With It earns revenue.

Harris has been working on Cool With It for about a year and a half now — the site is in private beta but he hopes to run an open pilot within the next couple of months. For now he’s busy spreading the word at TechBreakfasts and other community events. Luring in partner restaurants and bars depends at least somewhat on them believing Cool With It is a legitimate business.


And enticing users? Well, that depends on what they can get out of it. In other words it’s a classic chicken-and-egg scenario — the struggle of a two-sided marketplace.

It’s not an easy space that Harris is attempting to influence, but his concept of joining dating to restaurant, bar or venue marketing through incentives is intriguing.

Oh and Harris’s own relationship status? He’s engaged. They met on OkCupid.

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