Quora: "How can I be completely honest without seeming like an asshole?"

From my own experience (and I have plenty, unfortunately), it doesn't always work to say things nicely and the ONLY way to make sure it's not understood is, when you say something particularly sensitive, to always actually be  with them when you say it and be careful: keep looking them in the face to see how they react and choose your words accordingly. You will still be misunderstood, but the advantage is that you can immediately take your words back if you are. But don't take it too serious: people who are quick to judge and show little understanding aren't all that important anyway