When I was fifteen, I was friends with a girl who decided that to "strenghten our friendship" we should each tell one thing we didn't like about the other's appearance.
I wasn't really sure how that was going be a good thing, but she went first and said, "I don't like it when you wear combs in your hair. Everytime you show up for school like that I'm like, 'No! Not the combs!' I just thought you should know."
By the way, they were this kind: Not this kind:
I blinked at her, feeling a bit like I'd been slapped and said, "Oh."
She got all smiley and said, "Your turn! What don't you like about me sometimes?"
Honestly, there wasn't really anything that made me look at her and think,"No! How could she humiliate me by looking like THAT?!" I had enough insecurities about my own appearance to worry about what my friends looked like.
I didn't particularly care for her haircut, but I knew that she liked it a lot. And saying, "I think your hair would look better longer" wasn't as easy a fix for her as me not wearing the combs. But she was waiting for an answer so I said the first thing that came to my mind, "Sometimes I wish you wouldn't wear so much eyeshadow."
The thing is, it wasn't even true!
Afterward, she talked about how this had made us better friends because we knew we could always be honest with each other. Secretly, I didn't agree because I hadn't been honest at all. I felt like she'd attacked me and that she'd goaded me into attacking her back. It made me feel kind of awful at the time. It made me feel kind of awful today--eighteen years later--when I remembered that it happened.
(And I know she'll never read this, but if somehow she does: I never thought your eyeshadow looked bad. You always did a great job with your makeup.)