An interesting question isn't it? One court recently said that three times was not too much harassment in a 4-year period. Brennan v. Townsend & O'Leary Enterprises, Inc.,
Harassment is not unlawful unless it is based on a protected class, is unwelcome and is either pervasive or severe. Pervasive means "a concerted pattern of harassment of a repeated, routine, or a generalized nature." The three incidents involved the boss requiring a woman to were a veil with a plastic penis attached received at a bachelorette party, the boss dressed as Santa asking woman to sit on his lap at a Christmas party and asking personal questions, and the boss wearing a Santa hat at another Christmas party with the word "bitch" written on it. (I bet those parties were interesting!)
The court said that Ms. Brennan was out of luck. It was not sufficiently pervasive. The Christmas party incidents did not even occur at the workplace. Nor was there anything "severe" coupled with the acts.
It is interesting to read the case. Ms. Brennan was close to Mr. O'Leary, the boss. She considered him a friend with whom she did share some personal information.
But when a job is lost or other issues arise, it is not uncommon for an employee to identify past acts as unwelcome and hostile. This is why it is so important for business owners and managers to keep a professional relationship with staff. Just like we hear on all the cop shows, "Whatever you say or do will be used against you in a court of law."
But then, if you are feeling lucky ... you may have three free shots. And if you take the chance I am here ready to defend you ... and take your money in doing so. (So don't take the chance.)