HMMM always take the best looking member of the opposite sex on your business trips? Or whatever turns you on.
That happened to me inadvertently.
A woman that worked for me needed help collecting field information on a project she was working on. She was still fairly new to field work in general, so this was a bit of a learning opportunity. It was going to require an overnight stay. She arranged the travel, and I just kind of assumed she was familiar with our typical arrangements.
We travelled to site early, and put in a rather long day, and headed back to the hotel. There was only one clerk working the desk, so she checked in first and I waited in line. As she wraps up she turns around and hands me a key and says lets go.
This was the first inkling that there was a misunderstanding.
I asked if she had booked two rooms:
"No. Don't you guys usually share rooms?"
"Uh, no. We share apartments or townhouses, not hotel rooms."
"Oh. Oops. I didn't want to be treated different than anyone else, and I thought that's what you guys did."
"Had I known, I would have brought pyjamas."
Turns out the hotel was booked solid with other contractors.
Now we had been pretty good friends since 2007, so awkward as it was, it could have been much worse. The night was of course uneventful, but word eventually got around the office, which raised eyebrows.
There weren't any repercussions, but I made sure that my folks were up to speed on travel guidelines.