Posted: Nov 1, 2005 7:14 am
Well, depending on where she works, you could actually be a "creepy" guy. If she waits tables, bar tends, or otherwise works in a service job or retail where she interacts with the public, then you have some latitude. If she's an account executive on the 12th floor, and you choose to drop in on her unexpectedly while at work, you may find yourself escorted from the building in handcuffs. You've left far too much latitude for anybody to be of much help.
If you don't know her, how do you know of her?
If she does have a service job, whatever you do, don't drop in on her while her place of work is busy. Then you will prove incredibly annoying. Drop by when it is slow, order very little, make friendly small talk. Unless she straddles you in the chair, you should not make even the slightest hint of an advance on her. Give her a good tip and leave when she's not around, when she's gone back in the kitchen. Then go back a couple days later and see if she remembers you.
Does she work in a book store? That's easy. Ask her what to read. Find out what she likes to read. Do likewise, then you will have tons of stuff to talk about. At least a book's worth of conversation.
For some reason women love self depricating humor.
Where she works, what she does will make all the diference in how you pull this off.
Best of luck.