How To: Deal with a flirtatious boss or sexual harassment

He's not exactly demanding sexual favors, but his flirting is getting really gross. What's a girl who likes her job to do? You will need diplomacy and documentation. Assess his behavior. Now, don't be offended, but we have to ask: Is he really coming on to you, or is he just a sociable, flirtatious kind of guy? If it's the latter, just ignore it. Do your part to keep the relationship professional. Don't chat about how your last two boyfriends cheated on you and then expect him to know that discussing sex is off limits.
Step 2: Discourage his behavior passively
Discourage his behavior passively. If he stands too close, step back. If he suggests you should do something outside of work or floats a sexual innuendo, suddenly remember a pressing work-related question or stare at him blankly.Confront him. Ask to speak to him privately, and let him know that while you appreciate a laidback office atmosphere, his "friendliness" is distracting you from doing your work. For diplomacy sake, make it sound like your issue, not his. Use neutral "I" arguments like "I feel uncomfortable discussing Brazilian waxes with you," as opposed to the accusatory "You're making me uncomfortable." Document everything
Start keeping a file on every inappropriate thing he says and does so you'll have back-up if things get out of hand. Report him.
If he refuses to shape up his act, or if his behavior feels aggressive or threatening, file a formal complaint with the personnel department. Sexual harassment isn't in his job description, and dealing with it shouldn't be part of yours. 17% of women responding to a Harris Interactive poll said they have felt sexually harassed at work.