Help! My boyfriend dressed up as his boss for the company Halloween party, then his boss went missing under mysterious circumstances…

Mara Macduff
Help! My boyfriend
Published in
2 min readNov 3, 2024
Credit to Dylan Gillis on Unsplash

Requesting to remain anonymous. Thanks.

My boyfriend is a really great guy, but he tends to be a bit of a class clown. For his company Halloween party, he dressed up as his boss, who’s this older guy with a good sense of humor. Everyone had a good laugh about it, and it was actually a really convincing costume. The party went pretty late because it was on a Friday, and I left a little before midnight because I had stuff to do the next day.

Flash forward and my boyfriend tells me that nobody has heard from his boss in a couple days, and people are getting nervous. Now, here’s where the situation gets tricky. Like I said earlier, my boyfriend had a really good costume. Would it be wrong for him to dress up as his boss and take his place until he is found again? My boyfriend thinks it would give the employees peace of mind. Any thoughts?

-Anonymous

Hey Anonymous,

First, compliments to your boyfriend’s creativity and sense of humor. I’ve met several people who’ve been fired after dressing up like their boss at the company Halloween party, so he must be pretty charming to pull this off. Hats off to him!

For your question, there’s one glaring issue with your plan. How is your boyfriend going to be his boss and himself at the same time? Maybe he can say that his original self got a different job and moved away, or he can dress as his boss whenever ‘he’ isn’t in the room. That sounds complicated, but it’s doable.

You’d also have to contend with the police. They might ask your boyfriend (dressed as his boss) what happened, so your boyfriend will need a solid cover story. You also need a plan for if anyone actually finds his boss. He might get upset at the fact that he’s been replaced.

Otherwise, I think it’s a good idea. Nothing is more important than the wellbeing of ones’ coworkers, so your boyfriend is doing a service by taking one for the team and dressing up as his boss. Just don’t spend his entire paycheck! LOL

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Help! My boyfriend
Help! My boyfriend

Published in Help! My boyfriend

A blog where I try to help your boyfriend overcome his problems, ranging from criminal indictments, unconventional fears, strange tendencies, and many more. Can someone give this poor guy a break?