Hmmm, this is always a tough situation to be in.
It sounds similar to when I first met my girlfriend. It was frustrating because she always drooled over the tall, lean, dark haired guys and I was a pre-t, pre-op, big chested "man-woman" at work.

I hinted to her friend about liking her but her friend told me that she liked other guys and probably wouldn't be interested. But I ended up telling her when we were drinking together.
It took her a while to get used to the idea and she even went off and dated some other guy we worked with but then she broke it off and asked me finally to go with her. It made me really jealous and angry of course but she explained to me that she was too afraid to like me and was freaked out by the idea at first.
She got used to the idea very quickly and never did anything after that to make me feel like she thought I was less of a man.
So I wouldn't try to rule yourself out based on what her friend thinks. If she's known you for some time now then she too could be liking you more from getting to know you. Plus you have the advantage of having surgery (top surgery I am guessing?) And I am guessing you are also on T? I know that doesn't make you more of a man but it helps others see what you see right.
Maybe try casually asking to hang out with her and see how that goes.