Obviously common sense prevails like be respectful and do it tactfully, but life is short just do it. Maybe its me being in the shadow of middle-age but seriously.

See I think a lot of feminist polite guys like me blow our chances because we're scared it'll scare them off, but what's the worst that can happen, they just say they don't feel it back, you have an awkward moment and laugh then you just go on with your lives like before? I told this one friend after a bunch of her failed relationships, and that guys would be lucky to be with her. She said she was really flattered but didn't see me that way and I was more like a brother/bff and I apologized if it was awkward but just wanted her to know somebody feels that way about her, and everything was fine and we're still friends.

Also I bit the bullet and told the family friend/babysitter I reconnected with from the early 90s (she's almost 50 now) that I had a crush on her as a kid and that "I hope its not awkward but you're really awesome and beautiful now" and she told me how sweet it was. Her husband apparently is kind of a dirtbag and makes fun of her weight and stuff, but we've been flirting back and forth over Skype, I'm sure nothing will come of it since she's 2 states away but I wouldn't want to die knowing I never told her.