I am a psychiatrist and I work with chronically mentally ill patients who mostly live in group homes run by the company I work for.  Several of those group homes are on the  same campus as the clinic where I work so there are patients roaming around outside everyday.  I have worked for this company for almost 4 years and been at this location for over 2 so people know me well but you can imagine given my position this could be really awkward.  I decided up front to be honest about it if asked directly.  Ive been totally honest with co-workers because I have needed their support and understanding in my recovery but patients have said things like "you lost a lot of weight" and I just say "yes, I have". No patient has actually come straight out and asked me how I lost my weight.  But I decided if they did, I will tell them because I don't want rumors to start and I don't want to keep track of what I told to whom.  

I decided to leave it for now and if he says anything again address it directly and tell him he's making me uncomfortable. Thanks for all the input, it's helpful to hear what everyone else thinks about this!

Have you ever thought he may have had a relative with an eating disorder?  He doesnt know and from his eyes you are losing weight rapidly.  Maybe he is scared you are puking it up, or starving yourself or crazy exercising.

Dont take it as him being mean or uncomfortable. Just as he DOESNT KNOW YOUR WLS history, you DONT KNOW HIS PERSONAL HISTORY.

If anything, take it as a compliment your hard work is paying off and move on...

And if you must tell him something.  Tell him the truth: I.e. smaller portions. I only eat 1/2 cup meat and 1/2 cup non-starchy veg per meal.

You have told him the truth.... just not all of it.

I've already decided how to handle this (by not addressing it again unless he brings it up and then I will ask him to stop making the comments).

But just because I don't know his personal history doesn't give him the right to address these things to me. Especially since he's a man with higher seniority, more importance in the company, and so on. He is definitely not hitting on me, but any man asking these questions would make me uncomfortable. Unless he came to me and TOLD me his personal history and then asked me questions - which then I would most likely be like Oh, okay - but without any explanation, it makes me very uncomfortable.

People can be so clueless! It's like they really don't think before they speak either. I think that's all that was with Troy.

I didn't tell anybody about my WLS but I told them about the hiatal hernia repair part. When I told people I'm having my hiatal hernia repaired they would say "why?" or "are you sure that's your only option?" or "Who's your Dr.?", "can't you just control your symptoms by what you eat?". Matter of fact every person I told asked who my Dr. was. Why the heck does that concern them?!!! I don't know you outside of work! 

Ask him how much money he makes. If he's not completely dense, he'll get the picture. ?