So we've started off playing with some free online dating sites. There are tons out there when you search, and they are generally crap. These are probably the only ones worth looking at.
PlentyOfFish - Horrendously ugly UI, but it seems to be one of the more functional and popular online dating sites. Seems more popular in Canada than the US.

OkCupid - They've recently revamped their UI, and looks much better. Most of their online dating centers around taking surveys and tests
Craigslist - Enter at your own risk. There are so many creepy people on craigslist. I once got a reply from a girl who on her MySpace had pictures of her cutting herself. Also, girls get about 1 post per minute here, and there are a lot of fake posts for porn sites.
There are actually a ton more out there, but most of them are the same and with relatively few users. If there's no one on a dating site, what's the point of using it?

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