Quote - (they most likely wont be a twentysomething hot chick, more than likely a woman in her thirties)

Hey! Don't discount us "Cougars!"  God I hate that term!  LOL  
If he joined a dating site, he could very well meet an older "mature" woman who isn't shallow, or who has gotten over her shallowness with age and time.

A tip for the original poster about dating sites.  Be wary!  When I had signed up for a couple of those free sites I heard from several guys that many of the women who contacted them or who they contacted were actually "pros", meaning they were using the site for purposes of prostitution.

Also, very few people find lasting love on those sites. Many are in it just for an affair.  Luckily you are a guy looking for a girl.  Girls looking for guys for a serious relationship on those sites have it much harder. Based on my experience a good majority of the guys claim to be single when they are married or in a relationship already, looking for a bit extra on the side.   In fact a co-workers husband hit me up. He didn't know it was me, and it took me about a hour of chatting with him to figure out that there were too many co-incidences between this guy and the husband of  a girl I worked with.  The dope sent me his driver's license picture. I called him on it. He blocked me from contacting him again.  I didn't do anything, but I sure wanted to tell her.  To this day I regret not saying anything to her, or even just leaving a screen capture of his profile complete with his driver's license photo on the conference table.

Anyway, good luck to Joster in his quest for social freedom.

"It is good to see ourselves as others see us. Try as we may, we are never
able to know ourselves fully as we are, especially the evil side of us.
This we can do only if we are not angry with our critics but will take in good
heart whatever they might have to say." - Ghandi