I Got Drunk and Fucked My Boss: Now What?

Dear Robin:

I am freaking out and don’t know what I’m going to do. Friday night I was out with some girlfriends and I ran into my boss Chris and some of his friends.

Long story short, our two groups hung out all night and I had WAY too much to drink. He gave me a ride home and one thing led to another and we had sex.

He left really early the next morning and I haven’t heard from him since. I just called in sick and I’m sitting here panicking because I am so embarrassed and worried about how he will react when he sees me.

Help! What do I do?


(This letter will look familiar to my most avid readers.  It originally arrived on a Monday morning and is the #1 blog I’ve written so far.  EVERY DAY the top Google search terms leading people to this blog are “got drunk fucked boss.” Maybe I should write exclusively on that subject since so many people seem troubled by it.  Those of you visiting today because of that search: please share and subscribe!)

Dear Sally:

I had another column practically finished when I received your email this morning. I thank you for your letter because it gives me the opportunity to help someone in real time! There you are, hiding in your house and avoiding work as you wait for me to deliver my pearls of wisdom regarding your, er, sticky situation.

I wish you had reached out to me before calling in sick because that was Big Mistake #2.

Big Mistake #1 was obviously letting your boss go spelunking in your love cave.

Take Control of the Situation.

When we emailed you told me you didn’t use protection when Bossman put his pork filling in your won ton.

Immediately after reading this please call your OB-GYN to schedule an STD test and then proceed to any store that sells Plan B unless you either want a baby or you work for Hobby Lobby.

Do not call in sick again tomorrow. You need to get right back to work with your held held high and your dignity intact.

By calling in sick you are sending your boss a message that you can’t be professional under duress and also that you think you did something wrong.

You didn’t.

You did something stupid, but it wasn’t wrong.

Your boss Chris, on the other hand, really screwed the pooch that night (figuratively: I’m not trying to insult you). More on him in a moment.

I won’t berate you for stupid behavior because what’s done is done: you can’t put that cream back in the pastry bag and everyone has done some epically fatuous shit when wasted.

Instead I’d like to caution you about unprotected drunken sex, and by “caution you” I mean hit you square in the face with the AskDesCamp Velvet Hammer of Truth:

Letting a man burp his worm in your garden without protection is crazy.

Three Reasons Why Sally Needs a Box of Condoms and an IUD:

  1. You are very young and don’t want children until you are married (good girl!). If you continue screwing around without birth control you will either have a baby you aren’t prepared for or you will have to endure the anguish of the other two options: adoption or abortion.
  2. Sexually transmitted diseases are everywhere and you are not immune.
  3. Condoms make clean-up of your Hot Pocket® much easier, so get a box today!


Sally’s Boss Messed Up Big Time

Chris is the one who should be in hiding, not you.

He is much older and is in a serious cohabitating relationship with another woman – a relationship you didn’t know about until 30 seconds after his baby batter dribbled down your thigh and onto your Scooby-Doo sheets.

He also heads up HR for your company and conducts seminars on sexual harassment. What a fucking moron. Does he move his lips when he reads?

Some people are waiting for me to accuse him of rape, since you said you were drunk.

I’m not going to do that, because you told me you very much wanted to screw him Friday night and you were alert and awake throughout the entire 5 1/2 minutes of fun.

Contrary to current popular belief I don’t think alcohol equals abdication of personal responsibility regarding the choices women make, especially when those choices look really bad in the cold and sober light of the following day. See: Oregon Basketball players fiasco.

Look at it this way, Sally: he is probably a lot more worried about this than you are, and he should be.

He has a job and a relationship on the line and suddenly this 24-year-old underling (literally!) has an enormous amount of power over him.  This is a very good time for you to ask for a promotion and a raise.

What Should Sally Do (Besides Not Fuck Her Boss Again)?

You told me you want to move into your company’s marketing department and I think that’s a great idea.

There is no happy future in HR for you anyway.  HR is the 2nd-most depressing line of work there is (the first is Gas Knob Turner at the animal shelter when “Adopt a Friend!” day gets rained out and there’s no money in the budget for kibble).

Meet with your boss and tell him you would like his assistance in transferring to an upwardly-mobile job in the marketing department for which you are qualified.

I would not directly address your activities of Friday night, but rather raise your eyebrow cynically should he balk at your request. A properly raised eyebrow can accomplish much.  


Once in a while life gives us the opportunity to make lemons into lemon-infused cocktail drinks.  Take advantage of this monumental fuck-up to get a better job and distance yourself from your boss. 

Three More Pieces of Advice for Sally:

  1. Keep your mouth shut. You told me you have become close friends with one of your co-workers and you considered speaking with her about this. Under no circumstances should you do that.You may think you can trust her but someday she may not be your friend anymore and she could not only spill your secret but twist the story and after that nobody will take you seriously. 
  2. Start taking very careful notes if your boss takes any punitive action against you or harasses you in any way. Write down your memories of Friday, such as they are, and keep a journal should things go south at the office. He may decide to double down on his incredibly poor behavior and try to get you fired. Watch your back and protect yourself.
  3. If this evening was a one-off bender and not at all customary that’s one thing, but if binge-drinking and concurrent poor decision-making is a habit of yours, look closely into your relationship with alcohol. I would help you do that but I can’t because I am already over my word limit and I’m too hungover to be helpful.

Please write me back with an update.  Readers, please comment and SHARE!!!


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