That a woman gets emotional or freaks out when you try teasing her?

Growing up, my mom was mentally/emotionally immature and when i would try to tease her or makes jokes about her (as shithead little kids do) she would guilt trip me or have emotional outbursts due to my "Constant criticisms". HS was no better as the girls would behave similar to my mom reinforcing my habits.

This i feel is a major contributer to my fear of flirting and pushing boundaries; im afraid what i say will be misconstrued and the woman will make some type of scene.

Ive made a few approaches here and there, but this is a thing that seriously impacts my motivation