I have only made the first move once. I had been single for awhile and was ready for a life partner. So I decided the only way I was going to get that was to pick him out instead of settling for the usual suspects whom asked me out.
It took me four months to work up the nerve to ask this incredibly hot guy out who I hired as an IT contractor for my work. I literally used to screw the system up just to get him over to 'fix it'. In the end I was still too chicken shit and asked him over e-mail. Lame? Yes, but we have been happy ever since.
