Sure, personal ads are one of the biggest money-makers on the web, with everyone from InterActiveCorp to Friendster being involved in the space, and of course content-targetted ads are raking in huge bucks for Yahoo/Overture and Google, but has anybody combined the two yet?
I want to see content-targetted personal ads on the websites I visit. "Single? Looking for someone who loves blogs? Click here!" And then all the lonely web surfers could buy keywords for their ad to appear on. But then I guess that's what Jeff is talking about, that keywords aren't good enough. We should be targetting the people that visit a site, instead of the merely words that appear on it.
So, to all of you looking to share your profile with the world, I'll have it be known that this is still the number one result on a google search for anil sex. If you're looking for illiterate sodomites, have I got a bargain for you!