A close friend of mine has had a fairly significant weight change over the last two years. She's very insecure about it but seems to be trying to counteract that by making a joke of it.
I've gently told her a few times that it doesn't matter and it's been a tough time for everyone. I've said to her that her jokes are unkind to herself and as someone that cares about her, they're upsetting. We last had this conversation a couple of months ago.
I spent Saturday with her and we went out for a meal and I quietly counted in my head- she made 16 jokes about her weight in one day. Sixteen. It's things like, we went for a walk during the day and she said 'I really like walks- but you wouldn't think that to look at me!' or she didn't finish her meal and said 'I know its surprising when I'm such a big fatty!'.
It hurts me to hear her talking about herself like this but we've already had a chat about it and I don't know whether its worth bringing up again or letting her continue to tear herself to shreds.