Don't you think jokes are subjective?

We all know that jokes are meant for fun and entertainment purpose but we also know that not many people who know how to joke have the same value in joke. Take this as an example: When someone ask a question like “what should I do in prostitution field?” Others might answer like “Aren’t you a bitch?” And of course each person and the OP will have different value for this. I usually feel offended when I got such answer in my question. It would be hard since most people will know whether or not it’s a joke by tone and intonation,and of course it would be hard to shown in hand writing(even after you add a “LOL” it could be considered as teasing). Clarification would be invalid since the offenders might also turn their ‘insult in disguise’ to what sounds like real joke.

I can’t believe how many times I said “joke” here. Anyway,did you usually joking around? Did you ever feel guilty if somehow your joke could offend someone? What are your criteria when a joke is far more than just a joke? Is there a border between joking,teasing,and insulting?