it was after months and years of seeing him be confused, reject very good girls, educated, smart, good looking because well they did not have the look he was looking for. and then getting all down because when he did find someone he liked they were not interested. I had to sit him down and talk about that when he is looking for a total package, the girls are as well, and while he is a nice guy, a doc who will be making half a mil etc, he simply is avg in looks and sub par in grooming and dressing. it resonated with him because he started taking better care of his appearance and grooming etc.
a friend has to be brutally honest sometime..yet still deliver it in a sensitive manner