Cool, I’ll just take one point at a time. Let’s start with this. :
Student: “And I insulted this particular girl when I commented on her clothes. I told her that she was wearing all black and told her that if she’s going to a funeral.[private] I should’ve just made a quick comment on it like, “Okay you look nice, but you’re wearing all black, you going to a funeral? =)” with a big smile on my face. Oh yeah I remember what ticked her off, I said after that, “Who dressed you up? your mom?” Then she got pissed. I think I went too much push on that one. ”
You only need one push or one playful insult/tease at a time. Then you can balance it out with a pull or a playful flirt back at her after it.If you have one joke, she’ll take it as playful but if you keep making negative comments about the same thing about her, she is bound to take you too seriously.
Once you have joked about something about her, move on and change the subject unless she gets playfully defensive. If she does get playfully defensive, you can later tease her in the same way but don’t keep giving her shit about her clothes. in different ways, then she’ll take you seriously.
Good experimentation, that is what will teach you the best ways to do all of these things.