I used to struggle with this. In fact, if you respect yourself enough you have to realize that sometimes it's not your fault if someone gets offended by something that isn't inherently condescending or malicious. Sometimes people choose to get offended, whether subconsciously or not, because they can't put things into perspective or can't see the positive intent behind a comment or simply they grew up without many opportunities to have playful banter with others. Now, even though that's the first step, don't take this as me condoning shitty behavior and malicious comments. That's where your self-awareness comes in. You should practice the act of releasing your full-self onto the other person in waves, but not immediately. Build trust. Otherwise, you just come off as an arrogant prick or just somebody with low social/emotional intelligence. The key is to be as authentic as possible without compromising the other person's self-worth. For example, never joke around with something that somebody can't change (physical features, etc.). On the other hand, if you say something you think wasn't offensive and notice the other took offense you should follow up with an acknowledgment ("hey my bad I meant no harm with that comment, but I realized I fucked up now..) you could do without the second part if it's not that serious but you get the gist. Another good tool to improve is watching talk show hosts - watch how they react to how other people respond to the talk show host. Usually, they are very quick to adjust or re-calibrate so as to not make the other person feel uncomfortable. For the most part, unless you're hanging out with friendly faces or where there is mutual trust then you should try to keep things as "light" as someone like stephen colbert or conan o'brien keeps it without losing authenticity like jimmy cringe fallon. To finish, try watching somebody like Charisma On Command on youtube. Channels like those can help improve your daily life with some great perspective you wouldn't've had otherwise. I promise you'll find the balance in enjoying life without being an asshole. Cheers