I won't lie, you do need to work on your appearance slightly. Nothing a comb and different clothes couldn't fix.
But appearance isn't really what females are attracted to.
You have to be confident, man.
This is where a wingman would help you out; he'd probably take you to a bar in town and walk you through the whole process of picking up a lady.
If you don't feel comfortable contacting your boss, just read my goddamn fanfiction, and pay attention to the manner in which I conduct myself.
Act like that.