There is no objective line, but if your actions result in your friends getting hurt that is sad, and if your friends decide not to hang out with you because of the chances you'll hurt them again that is a fair choice. You may choose not to put effort into understanding other people's perspectives but this means most people with healthy boundaries will either get hurt at some point and leave, or recognize that is bound to happen and leave pre-emptively. So if you want friends that treat you right or a partner who isn't miserable, then you will have to put effort into understanding other people's perspectives.
Your friend was offended for a reason. People assume you care why or how to avoid it because that is a necessary part of any healthy friendship. If you do not care, then I hope your friend finds friends that do care so they, at least, can be happy. I also hope that you have friends and you are happy, but an unhealthy friendship does not make you happy and it barely counts as friendship anyway.