Ehh really depends on your boss. And honestly it depends on you also. If either of you can’t separate work from personal time then you really shouldn’t be hanging out. But for most of the bosses I’ve had, some lighthearted social time outside of work was perfectly fine.
Please tell me you can play a single campaign without playing the horny bard, buying slaves, or torturing goblin prisoners
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