> And getting a good spot for the dating keyword seems insanely hard.

Okay, how about this:

* Make a Windows desktop widget or executable that sits in the system tray and polls for active Internet connection. Whenever the user goes online, it checks with your server if any 'matches' for the user are available and if so, goes Coooo! (and notifies the user.)

* Make it available for free download.

* Submit it to all the freeware/shareware sites out there...

... and see your rankings (and PR) soar.

HTH

ps. If you're going to do this, do it fast, before your competitors do. ;-)