An example of a comment made with good intentions...
Brandon and I were watching The Big Bang Theory the other day, a show we both thoroughly enjoy. Brandon has a slight obsession with Sheldon, the socially defunct genius of the show, often saying things such as, "I wish I was Sheldon" which in turn forces me to shake my head in shame.
So, we were watching a scene including the normal gang of nerds, Penny (their hot blonde neighbour) and Howard's new girlfriend, Bernadette, who is equal parts nerd as the four boys of the show.
As the show fades to commercial, Brandon says, "I think Bernadette is much hotter than Penny, because she reminds me of you"
Though said with nice and good intentions, I couldn't help but cringe a bit that I remind him of the nerdy chick from the show.