I'm sorry to break the news to you, but you will never date my friend. It doesn't matter that you went to Harvard Law and are now pursuing a career as a surgeon. That doesn't make up for the fact that you are only moderately attractive. No one cares that you owned your own company or that your idea of a romantic gesture is buying her a book about how to get into med school with a message scribed in caligraphy inside. What the fuck does "I feel a mutual resonance between us" even mean?! You two are not the brass section of the marching band. Also, just because she never asked, doesn't mean she didn't find out you are 40.
Hold onto that Rx notepad for your Viagra,