I am much more comfortable around guys I know I will never be attracted to, and for this reason, I've had a few uncomfortable incidents with socially awkward males. I have a theory that shy people can always recognize other shy people and naturally gravitate towards each other. I'm always nice to shy guys because I see myself in them. Since they are not used to girls talking to them, they mistake my kindness for flirtation.
In high school, I was friends with an older guy. (It's not as exciting as it sounds.) He was kind of strange and played the tuba, let's just call him Tuba Guy.* (I have nothing against the tuba, but I just wasn't attracted to him). He asked his friends to ask me out and I had to turn him down gently through them. Poor Tuba Guy then avoided me for the rest of the year.
Then, there was this guy I used to work with in college, Awkward Co-worker,* who mistook my friendly conversations for invitations to stalk me. He would come into my room unannounced and start looking at my computer screen to see who I was instant messaging. He also once got it into his head that we were going on a date--even though he never asked me on one. I was a bit confused when he asked me what time he should pick me up.