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How To Handle Your Boss’s Secrets: ‘How to Get Away With Murder’ Advice for Wes Gibbons

How To Handle Your Boss's Secrets: 'How to Get Away With Murder' Advice for Wes Gibbons

Dear Captain Awkward,

I accidentally walked in on my law professor having sex with
someone in her office the other night. To make things worse, she’s married, and
I met her husband the very next day (he was NOT who I saw with her that night).

The whole thing was my mistake. I should have knocked and waited
for an answer before barging in, but I was excited to give her a piece of
information I’d found out for an urgent project we were working on. Working
with her is very competitive, and I was so anxious to impress her that I jumped
the gun without thinking.

Obviously, her private life is none of my business, and I said as
much to her when she and I had a one-on-one conversation later. I had been
terrified that she’d kick me off the assignment or find some way to get back at
me professionally for knowing what I know, but actually the opposite happened.
She started confiding MORE personal stuff about her marriage and got a bit
touchy-feely. The touching was halfway between a maternal shoulder-pat of encouragement
and some sexy chest-stroking, plausibly deniable in either direction.

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She also promoted me to work on a special project with her. I
tried to turn down the job — I don’t want a promotion that isn’t
earned as a bribe to keep me quiet — but she said it had nothing to do with
what I’d seen and that I should be more confident about the quality of my work.

Captain, it’s only my first week at school and on the job. I look
up to this woman, and I really want to do well here. I think that working
closely with her could open a lot of doors for me. My preference would be to
forget the whole sex thing, DEFINITELY forget being petted like a pet cat, keep
my head down and do my work. But I don’t know if that’s really possible and I
don’t have much of a poker face. What’s my best course of action here?

Fresh Meat


Dear Fresh Meat,

Have you heard the phrase: “Keep your friends close, and
your enemies closer?” You aren’t this woman’s friend, and you’re not her
enemy, exactly, but it’s interesting that she’s chosen a moment when you have
potentially compromising information about her to tuck you more tightly under
her wing. I can’t tell if it’s a sound strategy or hubris on her part. Bosses
do often try hard to hold onto underlings who can put up with their particular
quirks and who can be trusted not to blab professional or personal secrets. I
expect that’s doubly so in a profession like the law, where being jaded and
close-mouthed is a plus.

I would not be doing right by you if I didn’t remind you that
there are other professors and other mentors you could seek out. Ones who don’t
touch you weirdly and over-share with you about their private lives. You do not
have to sign up to be in this highly irregular and uncomfortable work
environment. You don’t have to put up with unwanted touching at school or at
work, and you would be within your rights to report that to the school if you
wanted to.

I would not be doing right by you if we pretended that reporting
her is not likely be without consequences for you, which is shitty and unfair.
You’ve got a true Devil’s bargain on your hands: Do the “right thing”
by reporting a powerful and respected person for a vague weird thing that is
hard to describe (even though you and I both know there was some Wrongness there),
or ignore the Wrongness for your own potential gain. This comes right form the
“How to co-opt victims” playbook.

So here are some survival skills for continuing to work with this
woman (since I think you’ve already decided to keep working with this woman):

— Don’t
assume anything about her marriage (open marriages are a thing), but don’t
gossip about it either. You’re doing the right thing by just staying quiet
about what you saw — it is none of your business.

— Don’t
trust her with anything personal about yourself. She’s not your friend or your
mom. You’re not equals bonding over shared secrets. Redirect personal
conversations back to work whenever possible.

— If
she does the weird touching thing again, ask her directly not to do it anymore,
and document the incident and the conversation. In
fact, document any and all weird shit that happens as part of your work with

— Document
your own work product and your learning process. Make sure you are getting what
you want out of the experience.

— Make
connections with other potential mentors — don’t get your entire professional
life wrapped up in this one person. Get to you know your other professors. Get
to know other students. You never know when you might have band together.

— Keep
your eyes open. You’re not the only one who has had weird experiences with her,
I’ll reckon.

— Have
an exit strategy. What steps would you take if this mentoring and working
relationship went to shit? What’s your alternate plan for getting ahead in your

And work on that poker face. You’re going to need it if you stick
with this lawyering thing.

Jennifer Peepas is a Chicago-based filmmaker and film teacher. She answers questions from non-fictional characters at her blog, CaptainAwkward.com. 

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