Stay in school.. I can't imagine why you guys are dropping out of school to "start a dating website". That said, good luck and I'm sure will learn a lot.
And especially for another dating site -- this is a market that many smart people have spent a lot of time thinking about, and unless you have something truly revolutionary which is hard to replicate, the odds seem stacked against you.
But again, best of luck. And think about using Yale resources as well like YES, your summers, etc.