Why do some people do or not do, say or not say, things based on who it might offend?

When in a conversation, you should, as you obviously do, feel free to speak your mind. People like you will often make friens with people who speak their mind and are prepared to debate. Just remember, when you talk with people stay clear of the 3 "Landmine Zones" which are:

1.) Religion

2.) Politics

3.) Wages

Other then that you're right, just don't be too surprised if your comments sometimes offend people you aren't close to.

Are you patting yourself on the back for being such an individual and boasting to the general public by making this statement, or do you really want to know?

Because people are worried about being judged or looked down upon for saying what they want.