This is such an interesting post! And it's funny how you knew each other for 18 years before discussing this -- but then, who would discuss this? To enjoy something and be entertained by something, and maybe most words and expressions in general, are taken for granted by everyone, and no one stops and asks if people mean the same things when they use the words. It's fascinating (if not surprising) that they don't mean the same things at all.

For me, enjoying entertainment would probably mean fanfiction, and I enjoy fanfiction by feeling very positive feelings -- pleased, thrilled, elated, excited. Sometimes I quiver in fear and dread when I'm afraid that something bad is going to happen in the narrative, and very rarely, I feel sad when the ending isn't happy (or isn't happy in the way I wanted it to be), but I don't read a lot of things that make me sad or anxious. I want to laugh and feel satisfied when I read, and those things happen when there are stupid puns and sarcastic dialogue and nifty, intellectually engaging narratives, plots and storytelling feats.

This is really difficult to explain so in the end I don't really know if we enjoy or are entertained in the same way or not. I hope you got something out of this answer though. :)