She was so unhappy with her job that she 'entertained' thoughts of quitting. [=she thought about quitting]
It now seems possible to 'entertain' hopes [=to hope] that the strike will be settled soon.
They enjoy cooking and 'entertaining'. [=hosting dinner parties and other social occasions]
(..) It's hard because you know each other so well. You know? You know all each other's tricks. It's like two magicians trying to entertain each other. You know, one goes, "Look, a rabbit." The other goes, "So?" "I believe that's your card." "Look, why don't we just saw each (..)1990 TvShow: Seinfeld Title: The Stakeout Season: 1 Episode 2