This is a bit embarrassing for me to explain, but I accidentally ended up dating my coworkers daughter. This is our second date and everything was going well. There was some errands she needed to take care of at the local grocery market and she told me she could get herself home, so I dropped her off. Well I needed to help a friend of mine on the other side of the city for the rest of the day. What I didn't know was that she left her phone in my car! I dropped it off in her mail box really late at night as not to bother her or anyone else. Well, we had a bit of a miscommunication on the phone and she didn't have a way home and wanted me to wait for her (I don't even remember this)...It got very heated and I figured we were through (we aren't seeing each other anymore).

So I thought. Well, my boss came up with this company bonding event where you bring your significant other or family members for drinks/food etc. My boss was speaking about it and naturally I am not interest as I don't have a significant other. One thing led to the next and he told me about how some guy really mad him and his daughter upset not to long ago. He was definitely not pleased about this guy and joking told me of the physical things he would do to someone who did that to her. Well I decided to show up as he's personally asking me to attend these events. So during our first event, as I was greeting everyone, I saw her there. She didn't see me, but I found out that she's definitely my bosses daughter. I quickly left and didn't say a word.

Well now it's coming to Friday for the second time and my boss noted that I left pretty early. I also skipped another one completely. He told me he wants to see me this time for sure, but I don't want to go for the reasons I explained. How can I tactically avoid this potential (and possibly job ending) disaster?

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    You might want to make it clearer that the relationship is over, it's not immediately obvious in your wording. – Jane S Feb 22 '17 at 3:31
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    This wouldn't be the same boss from this question, perchance? – Jane S Feb 22 '17 at 3:44
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    Is this a coworker or a boss? – cst1992 Feb 22 '17 at 12:52
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    So coworker's relative is actually bosses daughter, or am I getting this wrong? – gnasher729 Feb 22 '17 at 20:06
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    You seem to have some interesting stuff happen to you based on you question history. In the question you state clearly my boss but then say not your boss. Bit of miscommunication? She thought you were waiting and you thought she said she had a way home. I don't think you are telling the whole story. VTC – paparazzo Feb 22 '17 at 20:22

Short answer: Unless you plan to run away from it by quitting, you need to face the issue. It will eventually catch up with you the longer you try to avoid it.

I don't know if your boss's daughter mentioned the name of the guy she dated, or what you looked like, but the chances are that eventually you will run into her unexpectedly and it will come out sooner or later. Rather than skulking around trying to avoid your boss's daughter, the best thing you can do is the next time you see them at an event, stay. Approach and greet your boss, and if his daughter is there, greet her politely as well.

The longer it goes, the more suspicious your behaviour will be and the worse it's going to end up. It's already having an impact on your professional environment. Yes, it may cause you some difficulty, but when it eventually does catch up with you (and it will), it is going to anyway. The alternative is likely to be far worse, unless you intend to run away from the whole situation by quitting.

Take the initiative, act naturally and confidently, and apologise for the miscommunication regarding the phone if it is raised. Don't pretend it didn't happen. It did. Hiding from it won't help.

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  • I hope you mean apologise towards the boss and not the ex-girlfriend? I can also understand apologising towards them together, but certainly not towards the ex-girlfriend alone. – Migz Feb 22 '17 at 8:30
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    @Migz I meant both together. – Jane S Feb 22 '17 at 9:19

Have a private conversation with your boss in advance. The most honest thing you can do is to address the issue with your boss before the social event. The goal of this conversation is to inform your boss about your prior interactions with the his daughter. Apologize for being evasive, but remain professional, and explain that you only meant to avoid harming your work relationship with him. Most importantly, use language that helps de-escalate tension, which keeps the conversation civil and helps you maintain control without seeming too forceful.

The problem you described is primarily between you and your boss. Having more people around increases the risk of disaster. To avoid pulling in anyone else, find a time where you can speak one-on-one with your boss. If you wait until the party to reveal your previous relationship to your boss, then you risk embarrassing yourself and your boss in front of your co-workers. Your boss will not react well, and this may jeopardize your job.

Therefore, do not wait until the party to arrange this discussion. Critical conversations like this are best managed in a private environment. There are fewer risk factors to worry about, and it will be easier for both you and your boss to have an open and respectful dialogue. Good luck.

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I agree with Jane S that you need to face the issue. However, I don't think that letting it happen in full view in public is necessarily the best option.

It sounds like your boss is extremely annoyed at his daughter's ex-boyfriend. It is therefore likely that if he hears about this while face-to-face with you he won't be able to listen to any reasoning, and will just get angry with you. This will lead to a very uncomfortable work situation.

Personally I would write an email to your boss, explaining everything that happened from your point of view. The first time he reads it he'll probably be very angry to find out that you're the ex-boyfriend he's mad at. Hopefully, rather than coming straight to your desk for a slanging match he'll re-read your email and try to calm down a bit first. Then you and he might be able to have a sensible discussion about it, and preserve your working relationship.

Sample email:

Dear Boss

I have a personal issue which I feel could affect our working relationship, and I want to be completely honest and open about it. I felt an email was best so that I could order my thoughts and give you time to digest them.

{More or less copy first paragraph from your question}

I hope that you can understand things from my point of view, and I would like to apologise for any distress to you and your daughter. I would like to maintain a good working relationship with you, and am happy to discuss this further if you would like.

Regards, Hans Moleman

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    I would be very careful to make sure that "explaining everything from your point of view" not come off as making excuses/justifying OP's behavior. – jcm Feb 22 '17 at 16:33
  • @jcm - Yes, true. Wording this sort of thing well is difficult, hence why I prefer email (where I can write something then re-read and edit) than talking (once you've said it, it's out there). – AndyT Feb 22 '17 at 17:24
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    I think writing an email is the wrong thing to do. A chat will be better. You can gauge what the response is and able to offer further explanation as well. Do this at the end of the day – Ed Heal Feb 22 '17 at 19:31
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    I like your suggestion, just change it to a chat versus an email. I would not do any sort of communication on this via email. – Neo Feb 22 '17 at 19:41

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