I’m set to have lunch with a former boss, who I liked quite a bit but we were not social outside of work, but haven’t seen in person in a few years. I pulled her up on linkedin, and noticed that she is barely recognizable having lost a very significant amount of weight. When last I saw her she was morbidly obese, and though the picture is just a head shot, it is obvious that she has lost at least 100 pounds or more; I couldn’t even tell it was her. So, it’s not the kind of weight loss you can pretend that you don’t notice (also not the kind that likely happened without surgical intervention).
So, do I say something when we meet up, or not say something? I figured just an innocuous, “Well, you certainly look different!” could work?
She almost certainly worked extremely hard to lose the weight. I’d think that she’d appreciate you mentioning it. Follow Fiendish Astronaut’s advice. “Different” is not necessarily a compliment.
The last time I told someone they looked great after a big weight loss, she said “thanks” and told me it was the result of a long series of gastrointestinal issues. Of course, she was a client, and her medical problems were actually helpful to her husband’s immigration case, so it was useful information for me. She certainly wasn’t mad at me, though, for noticing.
“You look great!” And let her go from there. If she says, “Thanks!” You know not to ask anymore questions. If she says, “Thanks, I’ve been working out” or whatever, then you can proceed.
I wouldn’t say anything unless you saw her in person. As others mentioned above, she may have lost weight due to illness or other factors that makes her uncomfortable to be reminded of. But if you see her face to face and she looks healthy and vibrant, then by all means say “you look great!”
As someone who has lost a lot of weight, I vote for something simple along the lines of how they look great, fantastic. “It’s so good to you see again! You look fantastic!” and then like others have said, she’ll talk about it if she wants. I don’t think anyone wants to hear, “Wow! You’ve lost a lot of weight” because all that does is remind them they were fat. At least that’s how I feel. I know they mean the same thing, but for some reason, the wording makes a difference.
Even when I lost it because of illness, I loved it being noticed. “Lord do you look good” feels fantastic even if the reason for looking that way isn’t totally happy.
But that’s just you. Not everyone likes their appearance being commented on (even positively) and the more specific the comment the worse. So if you must say something “you’re looking nice” is better than “wow you lost a lot of weight” unless you know it’s someone who is into that sort of comment.