How do you flirt with sensitive women that bruise easily?

This may be just a bad habit of mine but normally when I flirt with women I'll playfully tease them. Some of it is sillyness while some of it is silly and non-serious negging.

But every now and then I'll run into this one lady who, as I get to know her more, is pretty sensitive with a lot of personal boundaries. Almost every interaction I have with her I feel like I just walked on a landmine when I come across one of her boundaries.
Recently I teased her by pretending to be shocked when she made some off coloured jokes and could tell I just hit some more mines.

Have any of you guys come across women that are like this and how do you engage with them?