Hi Captain,

I could really use your help with a situation I’ve been dealing with at work. My job is at a small marketing firm, and I have a lot of daily contact with our customers, both over the phone and by email (not in person). One of our customers, whom I’ll call Jim, has always been a bit of a weirdo. He has a tendency to get hung up on small details that are really unimportant, so he’s much “needier” than most of the people we serve, and everyone in my office suspects he has some sort of neurological or mental health issue, based on the way he communicates. For instance, on the phone, he’ll say one thing in a very friendly, “normal” way, and the next time he speaks, his voice will sound completely different and curt, almost as though somebody else has picked up the phone.

Anyway, my co-worker “Lindsay” and I have worked with him on a couple of projects since I started working here this spring. Recently it became apparent that he was getting us confused, probably because we have similar job functions and will trade off on work, and because we are both female and might not sound that different over the phone. At this point, Jim went and found pictures of both of us on the company website and saved them onto his computer, so he could “tell us apart” (which makes no sense, since we’ve never met). He also sent me an email individually telling me I was pretty, and he should have guessed, because I “sound so pretty over the phone.” He also emailed Lindsay and I jointly to comment on our appearances, and included winky faces and LOLs and the like which were not the norm for the professional tone we like to take in our emails. My (male) boss initially offered to speak to him about it, then changed his mind and said he’d let us decide how to handle it. We both ignored his emails and hoped that would be the end of it.

He called me earlier this week and immediately told me he was smiling because he had my picture up in his email and was looking at my pretty face. I completely ignored this comment and asked him a business-related question in a very serious tone, but he kept up the flirty comments throughout the call. Because I was flustered that he did not seem to understand professional boundaries, I could not think of anything to say to change the tone of our conversation, and giggled nervously a few times, which probably did not help his apparent impression of my willingness to participate in his flirtation. Now, every email that does not CC anyone within his own company is filled with the LOLs and declarations of how he “lives for working with [name of my firm].” I feel that each passing incident makes it that much harder for me to speak up and put him in his place. I dread talking to him.

My company is tiny, tiny, tiny, and we do not have HR. I have documented each of these exchanges, and have joked around about it with Lindsay and my boss. Now I don’t feel so jokey about it, I want it to stop. I think my boss could still address this for me, but I would much rather try to take care of it myself first. At this point, I’m at a bit of a loss, especially since the guy can be so Jekyll and Hyde, and was already weird to work with before he started with the creepy comments. Any ideas for me, that would minimize any damage to the business relationship? I’m not sure he’ll stop even if asked to directly, so I’d love some follow-up lines to reinforce my boundaries after the line is drawn.

Thank you so much for your advice. I wouldn’t normally be this shy about telling someone to STFU, but I’ve never had a customer get creepy with me before, and it’s obviously different than a random creeper encounter on my personal time.

Sign me —