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This free dating site is by far the best I've found. The caliber of people I have met through OKCupid is several notches above the rest. Interacting with the site is a BLAST, too. The writers are comedians, so prepared to be entertained!
I Can Has Cheezburger?
If you don't know what a LOLCat is, visit the site and be changed forever.
For Microsoft software developers, this site is a must.
It may sound skanky, but it's actually a great place to meet some nice guys (no, not for THAT!).