I have never seen the film "Tootsie", but now I want to. I nodded my head when he described what happened after the make-up artists finished making him look like a woman, and he felt not beautiful enough: "I think I'm an interesting woman when I look at myself on the screen, and I know that if I met myself at a party, I would never talk to that character because she doesn't fulfill physically the demands that we're brought up to think that women have to have in order for us to ask them out. There are too many interesting women I have not had the experience to know in this life..."
Every woman, I think, is intimately acquainted with this fear. You know you're interesting, inside, but you fear guys won't stick around to find out how interesting you are, because you look so ordinary and aren't some kind of bombshell.
There's always also a continual awareness of being "not beautiful enough": I see my friends worrying about their appearance/attractiveness a lot. I have friends who are nowhere near fat obsessing over how fat they are; friends who are, in my opinion, attractive but who believe they need make-up to cover up their so-called flaws; friends who are so insecure about their looks that they can't bear to look at photos of themselves, much less have anyone else see those photos. It's very sad.