@Bethany,
Congratulations brave Sister! I feel your situation about "different circumstances." Before I met my wife, a woman that influenced many people including myself with her winning ways was a best friend (knew her for almost 40 years) and I was totally in love with her, passed before her time. Tears here too. My wife met her and became friends too. We think of her often & miss her.
The bra, I don't think you should worry about it, I believe there are moob bras out there for men.
Jamie