Dear Bar Fly,
Sure! As long as the boss doesn’t have ulterior motives, or isn’t creepy I think it’s acceptable. That being said, the boss does have responsibilities. Invite more than one person, limit intake (self and others), be in a public place, suggest food and/or Uber when needed, and be mindful of how actions and words might be perceived in a more casual setting. Oh, and the boss should pick up the tab. I hope this helps!
Originally published on Quora