my fiancé was my boss’s bully in high school

[ResidentialBusiness]

This post was written by Alison Green and published on Ask a Manager.

A reader writes:

I am to be married next year and decided to send out save-the-dates early. I really like my coworkers and my boss and wanted to invite them to the wedding. When my boss received my save-the-date, they swung by my desk to congratulate me and we got to chit chatting. The conversation led to my boss asking to see a photo of my fiancé as they had never met before. I showed them a photo from my engagement and —

It was like the smile literally slid off their face. I asked if they were okay, and all they said was: “Is this who you are marrying?” I was really confused and had a very bad feeling.

I went home that night and asked my fiancé why on earth this person would react to his face in such a manner. My fiancé claimed to not remember them, but clearly he recognized them. After a huge argument, he revealed that he was a prankster in school and may have sometimes involved them in “pranks.”

I’m not stupid, I can read between the lines. “Pranks” are only funny when everyone is laughing and based on my boss’s reaction, it was clear they never found these pranks funny. We had another huge blow-up and only when I threatened to walk out did he reveal the full extent of these pranks, all the while telling me “he wasn’t this person anymore,” etc. etc.

The pranks were horrific, atrocious, and not funny. Once, on a dare, he and his friends took pictures of my boss in the gym locker rooms and plastered his naked pictures all over the school. This is just the least horrific thing him and his friends did. I’m disgusted that the man I love and want to spend the rest of my life with could ever be this person.

I returned to office the next day and requested to meet with my boss. My boss wasn’t in the office, and in fact took the next two days off. When they returned to work, they did not really engage with me or even look in my direction.

Now I am unsure what I should do. My engagement is almost over. There is no way I can marry my fiancé now that I know what he is capable of. I’m humiliated. I don’t have any friends who aren’t his friends too. My parents are telling me to move and find another job and marry my fiancé because he is rich and treats me well.

I’m unsure of how to navigate the situation at work, given that my boss really doesn’t want to engage with me. Any advice you can offer about the personal aspect of this situation will also be really appreciated.

First, full disclosure: something about this letter pings my “is this real?” alarm. Apologies to the letter-writer if it is; life is often stranger than fiction. But even if it’s not, it’s useful and interesting to talk about how to handle it if it turns out your boss has a history with someone important in your life. With that said…

A lot of people were very different as adolescents than they are as adults. A lot of people behaved badly toward others in their youth but learned from it, regret their behavior, and have resolved to be better people now. The troubling part to me is less that your fiancé was an asshole in school and more that he’s minimizing it now. If he originally didn’t come clean because he was ashamed, that’s one thing (although still not great). But if his position is that these were just youthful hijinks and no real harm was done and you shouldn’t be upset about it now, that’s about his character now.

And if the best argument your parents, who presumably know him, can come up with for staying with him is that he’s rich and treats you well … that’s really not good. (It’s also fairly insulting to you, as if that’s the pinnacle of what you could expect in marriage.)

You said you’re humiliated, and you shouldn’t be. You learned something about your fiancé and decided to act on it before binding yourself to him for life. There’s nothing humiliating about that. If anything, there’s admirable strength in knowing that sending out save-the-dates doesn’t obligate you to move forward with an enormous decision that you no longer believe is right for you, something not everyone has the wherewithal to do.)

As for the work stuff, you really have two options:

1. You can make a point of acting aggressively normal with your boss and just give him some time to get back to normal with you. Sometimes when you’re doing this it can help to go out of your way to find opportunities to have aggressively normal interactions, so that his most recent associations with you are normal work things rather than whatever was going through his mind when he saw that photo. Also, if you do call off the engagement, make sure your office (and therefore your boss) knows.

2. You can address it head-on. Set a meeting with your boss or raise it next time you’re one-on-one and say, “I saw the reaction you had to seeing Bob’s photo and when I asked him about it, he was evasive but I learned enough to understand he was a jerk in school. What I learned through this conversation about his character now was enough for me to call off the engagement. I’m sorry if that photo was an unexpected shock. I’ve always valued my working relationship with you and I hope we can move forward without letting him affect that.”

I lean strongly toward #1. I have a high tolerance for awkward conversations if they’re in the interest of getting everyone on the same page, but there’s a very good chance that #2 won’t be necessary after some time goes by … although you could keep it in your back pocket to use if things aren’t back to normal a few weeks from now.

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