Yep. It would be different, based upon different situation.
I'm very careful about how I compliment people, too. I have to be, as my birth unfortunately dictates to people that I will act a certain way, because that's the standard they've been given.
I'm also in the "comfort negro" boat, as well, because I'm a genuinely nice person, charismatic when I need to be, and a little strange and nerdy, too. Having said that, I also can pull off being crass and racy without being dirty or creepy. It's because I have made enough deposits in the clean territory that it's not seen as creepy, but as playing around or joking, because I'm not seriously like that.
I do like to toe the line, if possible, because it's fun to see how people react to neutrality and indifference.