to be honest I am not sure when GEEKY appeared-- maybe someone can enlighten us.
I also think that someone who was considered SQUARE was a person who did not keep up with the times. Not willing to take risks MAYBE.
others may give other suggestions.
Isn't geeky someone who is into science and IT etc etc.
Actually this site explains better about the word GEEK. there is much that I did not know about at all.
Geek - Wikipedia, the free encyclopedia
http://en.wikipedia.org/wiki/Square_(slang)