When your boss invites you on an all-expenses-paid vacation under the banner of friendship, your gut starts asking questions your brain doesn’t want to answer. Because even if it’s innocent, it’s not normal.
This 32-year-old man says his 38-year-old boss is incapable of drawing a line between her personal and professional lives, and it comes down to the fact that working is the whole point of her existence. This woman can’t separate it out.
His boss really enjoys taking their team out to dinner or having happy hours with them, and she’s extremely friendly with absolutely everyone they work with.
Earlier today, he had a 1-on-1 meeting with her, and he was blindsided when she invited him on vacation to Mexico with her.
“Fully paid by the company (she owns), but clearly not for work, as we don’t have any business there. I was caught so off guard that I didn’t know what to say and said I would think about it,” he explained.
“I don’t think she is into me, as she has had an on-and-off boyfriend for a couple of years. She said I’d have my own room, and she just wanted to treat me to a trip, and thinks we would enjoy the time together. This was all said without any hint of flirting or anything.”
He honestly has no idea what to do or what to tell his boss. His boss is an amazing person, and he believes her invitation is nothing but innocent.
He adores his job, and he thinks a paid vacation could be fun, but he’s worried that the vacation could, well, get weird. After all, it is going to be just the two of them at a destination that is popular with honeymooners.
I don’t think he’s wrong to hesitate and be cautious about how he plays this one. The trip might be harmless, but the dynamic isn’t.
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He’d be spending days off-the-clock with someone who has full control over his professional future, and that’s a messy place to end up.
What do you think he should do?
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By Bre Avery Zacharski
Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski
