Yes, but you have to actually be on good terms with the person for it to work at all. It'd be like me trying to spend a day with Joni or something. It wouldn't work - there would be yelling after twenty minutes.

I think it depends on 1) what you feel is condescending and 2)tone, which doesn't carry well in written conversation. I could see how it could be condescending, if in a tone I didn't intend there. Otherwise, it's just the way I say things.