I've told very close family only dh, ds (21), ex-SIL, adult niece and they were interested and non-judgmental. We don't talk about them really, they just say now and again I am doing really well. I haven't told the rest of my family (brothers, sisters, other adult nieces and nephews).
Told my hairdresser, I've been using her for 30+ years so I should have known better what her reaction would be. For years of yoyo dieting she was always the first to notice when I had lost weight and cheered me on so it felt awkward not telling her a few stone in when she was saying she noticed and asking what I was eating, how was I exercising etc.
She herself was severely obese in her late 20s, lost it all 20+ years ago, had a full body lift, does the whole fitness thing, PTs, boot camps etc and although she doesn't say anything directly, I can feel the judgement and wish I hadn't said anything.
The thing is, the perceived "judgement" comes from others being uninformed and not interested enough to learn more (as it is all pretty boring). If I come across someone who appears genuinely interested in obesity as a disease and medicated weight loss I would probably tell them, but otherwise it just a pointless discussion.