Was that a compliment?

When I was younger, my brother and his wife came home to visit us. I think it may have been a holiday of some sort. She had just given birth to her second child. It had been a while since I had seen her. I remember wanting to give her a sincere compliment. This is how it went, "Have you gained weight or lost weight? Cause either way you look a whole lot better!"

A rookie move. The situation is funny in retrospect, but how rude. No woman wants to even hear 'gained' and 'weight' in the same sentence; no woman. Then to say that either way she looked better - the audacity. Did she look like a victim of starvation or like Oprah? Neither, of course. Not until recently have I been able to really empathize with that situation.

Whenever I see someone I haven't seen for a while, they ask me if I lost weight. I say, "No, not really." Then they say,"Oh... cause you look a lot better. You look good. Fit." I instantly get a offended. Was I fat last year? I went to the gym like everyday.... thanks and cool.

You know what I mean. Like a compliment that seems to dig at you at the same time - a back handed compliment. A subtle hint that you have improved your awful, previous, self.

Here is one, "Wow! Did you get a hair cut?" -"No" -"Oh, it looks good." Maybe it is the words like 'wow' and 'oh' that make it seem bad. Like they were surprised, then disappointed that it wasn't an intentional change. The voice inflection gives them away.

"Are those new jeans? They look good on you" TRANSLATE: I am sure glad you have upgraded your wardrobe, cause you look like a slouch most of the time.
"You are smart" TRANSLATE: My first impression was that you are an idiot. I am so glad you proved me wrong.