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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 —

My Appearance is Irrelevant

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Dear Captain Awkward:

I am trying to not make this question sound like a pity party, but will probably slip up somewhere. Apologies in advance and gratefulness for making this the space you do.

I feel like I am just plain mean a lot of the time. 

It’s confusing because I try to be really caring and positive and encouraging to my friends, there’s just this fucking mean streak too. I also work in Profession where Being Kind and Supportive is a huge part of my job and I don’t have any trouble there. The few times my friends have been my clients (which is ethically fine in this field) I have felt lucky because I feel like they finally got to see me at my best.

But outside of that I feel like there’s just this continuous stream of negativity that slips into conversations even with people I love, and I dig at people in subtle and not-subtle ways and don’t even notice it until the words have already flown out of my mouth. 

I think it is a defense mechanism because I don’t do it as much when I’m around people I feel comfortable with, but when I’m in a new social setting or around people I’m not sure like me I am just like…negative thought machine word vomit spout. It used to be way worse, but it is still often enough to sting and be totally inappropriate. 

I avoid getting involved with people who I can tell are no-bullshit and have good boundaries because I feel like they would automatically dislike me because of it, which sucks because I really respect people who have those skills and I am working on them myself. Simultaneously, I try to avoid becoming close with people who aren’t necessarily good at standing up for themselves, because I’m afraid of hurting their feelings.

I’m also really hard on myself, like 24/7 negative self-talk, which I know is my stuff to deal with, and I’m working on getting back in therapy. I guess what I’m wondering about is how to deal with Jerkbrain: Externalized so I’m not always hurting people I care about and feeling like I have to avoid social situations so I don’t ruin them for the people who are there to enjoy them, not be insulted.

I already know that what I’m doing is shitty and I am trying to find tools to be able to stop, because shaming myself about it is, surprise, totally ineffectual. Tips? Tricks? Personal red flags to look for? Mantras to repeat under my breath in bathrooms at parties? 

Thanks,

Jerk but Trying

Dear Trying Jerk:

The negative self-talk and the negative other-talk are connected. So yes, please go back to therapy.

I’ve been in the headspace you describe, for sure. I believe the clinical term is “total misery.”

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Darling Captain Awkward,

Most of your writers are adults. They deal with adult men. I, a female in high school, come to you with a even worse malignancy… teenage boys.

Oh, but you say: teenage boys? They’re perfectly harmless except for the stray sexual innuendo or the occasional Death Ray Pimple. But I’m also a scientist and mathematician, and I’ll let XKCD summarize what I usually deal with on a daily basis: http://xkcd.com/385/. Maybe add a few more pimples to the guy though. And maybe have, say, a guy to girl ratio of 10 to 1. And maybe fill up that page with sandwich jokes. 
Ignoring them is difficult during activities and labs because we work in teams. I’ve tried standing up for myself but I don’t really do well in panic situations and I’ve ended up gotten in some physical scrapes (nothing bad, but I’m kind of weak). The school has made it clear that they will only slap these guys on the wrist because they’re “honor students.” Pretty much everyone I’ve talked to just tells me that this isn’t a big deal and that I should just let it go. I’m disappointed in myself for not being able to figure this out, and I feel (and have been told) that I bring this onto myself by not laying low and batting my eyelashes. Am I overreacting?  How do I deal with this in the future?

I try to make light of what happens but, really, I am brokenhearted. I’m upset that most of the guys are going to top colleges and that I might not get in. I hate myself for not being able to let this go even though most of them have graduated, and I hate the social standard that I’ve noticed– when talking to my guy friends, they always talk about something productive; when talking to my girl friends, all we talk about is guys and other trivial things, and they don’t want to change. Mostly I’m just sad, lost, and afraid (and that’s not helping me deal with any of this). 
So, thanks, and I would love to hear your input.
Sincerely,
Pi Squared
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