Usually I try to do some roasting with people, to get in the mood and have more confidence between each other. This works very good with men, however not so much with girls, specially on text since it is hard to see when a person is being sarcastic.

Taking this into account, how much roast is ok for flirting in person and with texts. Many times girls have gosthed me after I said something that might offend them and I don't know if I should apologize or they just tought that I am too unmature.