Because playing with your boss is really stretching your chances of employment

You are lucky. What is silly is you not even seeing it

I have met enough players and DMs with whom I disagreed or got their bad side enough time to thank the fact that I was happy I wouldnt meet them at work the next day.

Its the same thing as not working with your lover. If there is something wrong or bad happening at home, you dont wanna keep it going at work afterwards.

But to answer you, yeah I can. Ill torture kobolds instead. /s

Monopoly is fine. Dnd is another beast.

Ish. Dont shit where you eat. Its risky to play with coworkers, but really dangerous to play with your boss. I highly advise everyone NOT to do it