I'd argue that most of the time, speaking the truth (in a loving manner) is more caring than telling a person what they want to hear.  They may even hate you for speaking the truth, because it is uncomfortable, but that doesn't mean it isn't for their good.

On your original post, I basically agree, but would disagree on a minute detail.   Christians are always called to speak the truth in love.  We are not supposed to tell people what they want to hear, but what God's word says.  The slight nuanced difference is that I wouldn't call that judging.  We are just speaking God's truth. 

 I would call it judging because we have to judge what we think to be right or wrong. We have to discern the situation and decide whether to speak.

We are not judging the person, we are judging the act. And we are judging the act according to the Word, as that is our Law.