This Is Why You Don’t Let Your Boss Give You A Facial (Yes. THAT Kind)

Alias (DO NOT USE A REAL NAME!!): Angelboss

Comment: ‘Tis the season…so I thought I’d submit a holiday party hookup scenario. Here’s what has gone down:

My boss and I are good looking people who sit in the same adjoining space facing each other. We’ve been working together for 4 years and while there may have been attraction in the beginning, we are now like an old married couple. There are days we don’t talk at all and then there are others where we chat & joke around about non-work stuff. We’ve also traveled together on business trips, even one-on-one, and no lines have ever been crossed. I have never talked to him about my dating life. He, on the other hand, has been dating his now-fiancee for over 2 years and was over the moon when they just got engaged a few months ago. He has talked about wedding details and everything is all set for next summer.

Very randomly, I ended up going on a Tinder date with someone who ended up being my boss’s very good friend.We put it together almost immediately when talking about where we work. John and I hit it off on the first date, but I was concerned about the awkwardness of him being my boss’s friend. He ran it by my boss, my boss said we have a lot in common, and to go ahead without feeling weird. I will admit I had high hopes for John. Chemistry was there, and I assumed if he was a good friend of my boss, he would share a lot of the same values & could be a standup guy like him.Sadly,as most online dating goes, we went out 3 times & he ended up being a flake.The most we ever did was make out, and I decided he was already canceling too many plans, and stopped texting him back. My boss and I never talked about John, but I knew he knew since John had run it by him.

Fast forward to our holiday party…lots of wine at dinner and my boss & I end up in the same cab alone to go to the next bar. He finally brings up John to me, and I tell him that he was too flaky. My boss goes “yea, I don’t think he knows what he wants, but sounds like you were smart and figured that out”. At the next bar, everyone starts smoking weed & drinking…’s hazy for all. At 4am when we leave, my boss decides that we should take the same cab since we live in the same area. In the cab, he brings up his friend again, and I tell him I was disappointed since I thought his friend would be like him and I had hoped to find a good guy in him, blah blah. Maybe that’s what opened the floodgates, but my boss looks at me & starts kissing me. It was like some fantasy coming true. It didn’t end there. He came over to my place and we had sex. He was a bit dramatic saying “I was going to ruin his life” but continued on anyway. He had maybe thought about this more than me
because he asked if he could cum on my face, lick my asshole etc. It was all a bit shocking to me since he seemed a lot more vanilla in the office, but we did end up having a pretty good session. When he left, he said “we will never speak of this again”.

So here we are sitting across from each other again. I now know he’s a cheater and this disappoints me, even though I was an enabler. Is cheating this common? Another part of me is now attracted to him because of the thrill and sharing a dirty secret. I can’t help wonder if it will happen again. A part of my ego is stroked because this man risked his career and future wife for one night with me. Do you think it’s because I went out with his friend that he decided to finally make a move? I love my job, but is this a reason to look for a new one?

And the story gets better…my boss and John are heading out on some trekking trip this week for 10 days and will be sleeping in the same tent. So much weirdness….how can I dissect this?
Age: 40
City: New York
State: NY


So, let’s just get one thing out of the way: you’ve always had the hots for your boss. You didn’t happen to end up in a cab with him alone. You and he both made it happen. None of this transpired by chance. He didn’t accidentally ejaculate on your face. And, please, nobody goes for a facial in a random one off hook-up unless that desire has been building. That’s just not something you do first time out of the gate. In most cases, a guy only asks for that  if he knows that request won’t be met with the stink eye. Usually there’s been some talk or at least a few cues here and there that indicate we go that way. So I’m not buying that you and your boss were always professional and platonic. From one filthy girl to another, I see you.

You’re talking like all of this just happened to you and that you didn’t actively participate in this drama. You’re disappointed that he’s a cheater? Really? Where was that disappointment when he was blasting one all over your face? The mental disconnect going on here is staggering. Again I will ask a grown woman why she’s willing to let her boss she’s not even dating lick her asshole but went out with another guy 3 times and didn’t sleep with him. It’s The Disconnect Olympics up in here.

This guy didn’t risk anything for you unless you plan on turning around and ratting him out. Which you can’t do because you willingly slept with a man you knew was a) your boss and b) engaged. You’re trying to make this hook-up into something more than it possibly was. I don’t think you understand..the sad truth is, in situations like this, people usually believe the man simply because he’s a man and a woman has all the feels and therefore can’t be trusted.

To answer your question, YES you should look for another job. This is a disaster waiting to happen only because your boss is in denial of just how big of an asshole he is and you are sitting at your desk drawing hearts with his and your initials in them.

Look, I’m not judging you for screwing around with a guy in a relationship. I’ve done it. And it’s because I’ve done it that I have a pretty good idea how this story will end. In an attempt to pre-emptively thwart any possible drama that comes from cheating on his fiancee, he’s going to start painting you as a problem to people. You’ll be the crazy bitch who wants him for yourself. Which you do, but that’s besides the point. You will get the short end of the stick and he will will fabricate some ridiculous scenario to explain what happened. Then his girlfriend will get involved and she’ll be on your ass because she’d rather believe him than you.  You will not win.

And don’t even think about going to her and outing this little tryst by using the “If it were me I would want to know” excuse. Here’s why that’s total bullshit: you didn’t care one bit about her when you slept with her man. You do not care about her feelings. You care about you, just like I cared about me when I did it. We’re all assholes desperately looking to fill some void or cavity or orifice. The goal in life is to try not to be an asshole as often as possible.

Start looking for another job and take the advice your boss gave you and never speak of this again. Don’t utter a word of it to anybody you can’t trust, especially co-workers. Learn from this and keep it moving.


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17 Responses to “This Is Why You Don’t Let Your Boss Give You A Facial (Yes. THAT Kind)”

  1. Fyodor Says:

    “You’re talking like all of this just happened to you and that you didn’t actively participate in this drama. You’re disappointed that he’s a cheater? Really? Where was that disappointment when he was blasting one all over your face?”


    Seriously, though, don’t date at the office, particularly with people you work with, even if they’re single. The risk/reward is too skewed. Find someone who isn’t at your office.

  2. fuzzilla Says:

    Here I was thinking, “Man, my work life is so boring, telecommuting from home with my cat…” Sometimes boring is good.

    Moxie’s right. If nothing else, at least own your true feelings/motivations.

  3. wishing u well Says:

    This is not an episode of SATC. No good can come of this…get another job ASAP and pray that your professional reputation doesn’t take a hit. There’s hooking up with a coworker and then there’s hooking up with a coworker….more power to you but something to remember: the more adventurous you are with a coworker in bed, the higher the chances that it will get out in the office. Not everything is for everyone in every situation, and double standards are alive and well in corporate America. When it’s a coworker – it’s a good idea to be aware of this. That momentary thrill is not worth the consequences….listen to Moxie and move on ASAP. By February – move on (and use the opportunity to get a raise / advance your career). I wish you well.

  4. Snowflake Says:

    This line near the start spoke volumes of who this woman truly is as a person.

    “My boss and I are good looking people who sit in the same adjoining space facing each other.”

    She justified all of this because they are “good looking”??

    Right. Sure. Whatevs… Don’t shit where you eat. Simple rule of life. Good looking or not.

  5. Angel Says:

    Harsh but I guess deserved. I’m the person who wrote in the letter. For the record, we did not do any of the things he asked for. I said no. Those are not sexual activities I’m comfortable with … So we just had regular sex – oral and intercourse. Not that it matters. I am not drawing hearts. I realize it was a sexual fantasy for him that he drew out, nothing emotional. Maybe last chance before he gets married? I also know I don’t want to myself be with a cheater so his fiancée can have him.

    I should also let you all know that I just got a promotion (before all this happened) so he knew I will likely not leave soon when he propositioned me. I will start looking but I have to find a better opportunity before I just quit over this holiday party fiasco

    • nancy Says:

      Gosh, folks are being pretty harsh on you dear. don’t run away from the job especially if the promotion is something that’s hard to replace. maybe you can move to another group? does your boss have a lot of sway? would he also want you to move to another group? maybe he can recommend you for another position? am I being naive?
      I am interested in your question: “is cheating this common?” I think the answer is Yes. Yes. Yes.

  6. Marshmallow Says:

    Angel, you were with a cheater. And he was a sexual fantasy for you. You still haven’t owed up to your part of the drama. Why was it a fiasco? What did you expect to happen? You are painting him as a cheating predator, which isn’t entirely fair.

    IMHO, you are upset that he wants to forget or at least put behind him what happened and went back to his fiancé while you sit there with nothing.

  7. Spero Says:

    All of the above. And cancel that trekking trip. Your boss and John and you in a tent together for 10 days — smells like they’re setting you up for a threesome and you can NOT get away from anyone when there’s 1 tent and 10 days on the trail (speaking as an experienced trekker). The situation is already a mess, as everyone has pointed out, and this will only compound the drama. Why put yourself through that, and why enable a cheater for another go round? You can trek with friends. Whatever cash outlay you sunk into the trip isn’t worth it, even if it’s international. There are few things more miserable than being on a trip when stuck with someone you don’t want to be with – also speaking from experience there.

  8. Noquay Says:

    Get out of there now! You’ve already screwed up (pun intended), it can only go downhill from here. I would bet that he wants to be rid of you in the workplace as well. The only thing to do now is learn from it and move on, fast.

  9. DrivingMeNutes Says:

    “It was all a bit shocking to me since he seemed a lot more vanilla in the office….”

    Interesting. My secretary sometimes lets me lick her asshole after she brings me the mail in the morning, but I’ve never asked to jizz on her face. Different strokes, I guess.

    Posts like these always draw out the Human Resources commentary, insisting that your career is over because you had an interoffice affair. Add OMG cheating to that and the heads explode. Office romances are common – especially among single people, and they only rarely result in any sort of employment action or legal consequence. Cheating is common too. So, I wouldn’t go quitting your job over any of this just because a bunch of concern trolls on the Internet say so.

    • Julie Says:

      Its sex not imbezzlement. Just pretend you were too drunk to remember what happened and your boss (if he’s professional) will too.

  10. J Says:

    I know I’m going to come across as a huge price and possibly “judgmental” but it needs to be said. You slept with a married man who is your boss and you’re trying to come off as a good girl and almost as a victim. Your reputation at your company is gone. When you knowingly sleep with a married man all sorts of terms tend to be thrown out. It brings up character questions, most of which linger in the back of people’s heads. So yes, get distant from your boss, find a new job and start over. When the shit hits the fan only one of you are going to be out of a job and it’s sure as hell not going to be him even though he is just as much to blame as you are.

  11. Gabi Says:

    What is with people not understanding the axiom of DON’T SHIT WHERE YOU EAT! Cheating on a fiancé is bad enough, but cheating with a close coworker is so much more of a potential liability and also doubly as hurtful due to the emotional intimacy and physical proximity involved. Cheating with a random in Vegas or seeing a hooker are bad but this is WAY WORSE! WTF people, when will we learn??!

    Moxie’s advice is spot-on here; there’s no way for the OP to win or gain any leverage here other than admitting defeat and GTFO. The only way to win is to not play. Game over. Bye, bitch.

  12. alan Says:

    I don’t think this is all that serious. I’d evaluate the job issue after a few months have passed. Say late February in the cold light of a NYC winter. Trust me. Amnesia sets in. If you and your boss are not behaving inappropriately with each other and if you still really like your job, why rush to find a job that might not work as well for you. I hate to say it but you might find your job is even better (it goes without saying I mean that assuming this is your one and only tryst with your boss).

    That being said, I just passed my 61st birthday and my 38th year as a Manhattan resident. I’ve been a (virtually) sole practitioner in my profession since 1990 but worked for large investment banks for over a decade before that. Boy do I miss the holiday christmas parties I used to go to on Wall Street. I was very single back then. In particular the same once-a-year-only hook-up (we didn’t call them that back then) I would have after each company holiday party with the very wonderful (and single but also a single mother) head of our word processing department.

    Went on till I left the firm. Very harmless I believe. Probably should have taken it further.

  13. Paul Says:

    Is this for real? A 40 year old still bar hoping, smoking pot, and acting like a 20 year old? Tell me that’s NYC. After partying all night, this guy wants to lick her asshole? A kinky guy like that would have made his moves much earlier.

    Sounds like fantasy fiction.

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