Do nothing is not an option (not that you seem to consider that an option), because even if she truly is fine, the next employee he harasses may not be. An HR

Do nothing is not an option (not that you seem to consider that an option), because even if she truly is fine, the next employee he harasses may not be. An HR rep is, frankly, usually pointless, unless you have high quality HR with specialized training. They do serve as a verifying party though. Me? I'd interview this guy (not alone) to see if I thought he could learn (as atrocious as his behavior reportedly is, I've been very surprised by what lessons have simply never been communicated). If you don't have full confidence he can improve, he's a liability to you and should go. I'd also lead this off by talking with the female employee about what you want to do - It's not just about her (although she certainly deserves respect), but about what kind of a company you want to have - which employees are protected and which ones are not. Hopefully she'll understand.