Dating for nerds (part 1): problem diagnosis
p.migdal.pl
p.migdal.pl
Social awkwardness is a well covered subject in this and many other books. Even better, it's covered by people who have more than theory to back their ideas.
Though, the most common thing that is missing is not taking risks - most of the time nerd fail to ask question (and of course, rejection is possible - but still better to be stuck in a limbo).