(Upvoted)
That would not be a way to say it respectfully. Or desirably!
Probably the best way to think about what I mean by doing it respectfully is "would this make the person unhappy or uncomfortable?" If yes, that's not what I mean (this is a hard point for me to convey - I can say "respectfully" but it's hard to map to a case where the person isn't displeased, though that is what I'm talking about).
So what I would do (and was imagining). The person is comfortable with their weight. Ideally, they're happy, outgoing, achieving good things, being successful. The person enjoys eating ice-cream, they aren't going to change this soon, I know this, they know the things I know, and it's not a problem. If I thought it would bother someone, if there was nothing actually unique and useful I could point out to them, I wouldn't.
But if they asked me, while feeling pretty comfortable about themselves and looking to branch out, if I thought they might be able to lose weight, maybe be a little healthier, I would say "Yeah, of course!" (with the implication "You're certainly going to succeed, if that's what you want to do.") If they seem bothered, I'd mention that it's all good, certainly no need to if they don't want to. (Verbal tone here is important, and unfortunately difficult to express through this text.)
and if I knew them well,
I used this as a shorthand for "this is the sort of thing we could talk about happily, and that the person was interested in". (In my comment above, I mentally mapped to a case where I might actually convey helpful and/or unique information.)
None of this was very clear about my comment. "working to avoid any stigma", "respectfully pointing out" and "if they want more ice cream I'll support their decision" are tightly clustered descriptions of underly-specified things. The main thing is "is the person happy", "have I made them look bad," "are they interested," and "am I actually helping". I would point something out when the answers are anticipated-yes, anticipate-no, yes, and yes.
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Whoa boy, not any more!
I think you are referring to ice-cream discussions.