Everybody has a different tolerance level, and especially when you are in a relationship and you have problems with the “not taking joke so well” problem then with time and practice you can easily calibrate with each other. Usually girls suffer from this problem as when you try to be a little cocky and playful with them they don’t take it well and it becomes a turn off for you.
So, being funny and not mean is very much important when you are in a relationship, it all depends on the sense of humor of the other person, being funny and not mean is all about being flirty, teasing and communicating and that should be all confident and not intimidating.
Women have a total different sense of humor with a lot of emotional touch actually, like you would never know what state of mind she is in. before hitting on any girl, you must know how she responds, if she is cold enough and all rude and her conversation ends up with a pout then seriously you are not funny and all mean to her right now. Usually when you are going for a cocky and funny comment then there are ways like supporting your comment with another same comment or end the argument with a hug, because girls respond really well to hugs.
While giving a cocky comment, do try to make it sound funny, because the more lame it is the more offensive it will be to the other person. Make it more cocky and funny at the same time, which actually requires practice so that you are funny and not mean. Because when you are trying to be funny and not mean then of course you will be going through different situations and the more practice you do on your cocky comments the more you will be funny and not mean at all and your every comment would be cocky but full of confidence.
Its normally among the guys to crack jokes and be loud most of the time, and most of the times it is a total turn off for them, even when you are just out of a relationship and want to be in a new one then stop being that jerk and try to be funny and not mean, because whatever you will say will have an impact on the other person.
Guys enjoy these cocky comments but these are a total turn off for women. So practice the way you speak and comment, because when you are in a relationship every tiny thing matters and so does your cocky comments. So its good to be funny and not mean in a relationship than to be a jerk who is always a turn off for the other person.