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A good reminder that sexual harassment is said to be in the eyes of the beholder, i.e. the recipient of the pass(es).
Bottom line: however awkward or smooth the advances may be, are they perceived as welcome or unwelcome by the recipient? Because practically speaking, it's ALL about the perception and response of the RECIPIENT.
So use caution, fellas, as some women aren't able to voice their objections, and might feel uncomfortable standing up for themselves!
Also, some co-employees are actually concerned with their professional image (maybe even more so than the would-be dater?), and the aggressor is probably not even thinking about how the target may be worried about earning the reputation as the office skank, i.e. the one who 'dates around the office'. Believe it or not, some people at work are there to, ahem, actually WORK!
Bottom line is, if she doesn't respond to your advances, you'd be smart to back out gracefully and let the matter drop: you don't want to face getting served with a lawsuit and/or discharge! After all, is it really worth losing a job over this?
BTW, this video depicts an attempt at striking up a relationship amongst co-workers, and not between a boss/employee (where it's even MORE QUESTIONABLE). That's potentially 'quid pro quo' harassment, where a boss dangles career advancement in exchange for sexual favors (clearly wrong and illegal).
This video also conveniently sets aside the whole 'creating a hostile workplace environment' issue (which Letterman learned about the hard way), where co-workers can file a harassment claim EVEN IF they're NOT one of the parties of the incident, but simply witness the relationship (including hearing about it via office rumors).
In the case of hostile working environment claims, the question is, what would OTHER workers think if someone who was in a position of supervision was seen to be dating an employee, possibly doling out favors and promotion because of one's willingness to sleep with the boss? Do other workers ALSO need to sleep with the boss to get ahead? That's the angle.
Needless to say, the thicket is filled with bristles.... Easiest solution is, don't go there (because cases such as these often settle out of court for six-figures).