I know a few people who pride themselves on their unblinking candor. Most of them, in reality, just get a kick out of constantly shitting on people and they use "candor" as cover for their behavior.

Here is a good rule of thumb: Is telling someone something hard going to directly benefit them, you, or someone else their behavior is affecting? The go for it and give them constructive and actionable feedback. Just telling them they blew it, they are pissing you off, etc is just shitting on them.

OTOH, not giving people hard feedback because it is awkward is a betrayal of the relationship you have with them because you aren't helping them be better or at least understand the situation they are in when you could have just to save yourself from your own squeamishness.