Sure, encourage him. But also coach him for the inevitable "I don't think of you like that" response. Extra points if she adds "you're too good a friend".
Categorisation into the Friend Zone happens within minutes of first meeting. There's no way out of that box.
A lot of people in this thread are talking about impossible standards of wealth and looks and being in the top 20% of men or higher.
But not enough people are talking about this standard. Can you ask a woman out without making her feel scared? I think your fear often comes across as dangerous.
So, ok, fine. Asking women out is scary. I was young, I remember that.
But if you never ask anyone out what are you really complaining about. And if all you ever did was ask one person out, get rejected, and then you've been sulking about it every since, that's not any better.
Hard is not the same thing as impossible. Hundreds of millions of men have figured this out.
Sure, encourage him. But also coach him for the inevitable "I don't think of you like that" response. Extra points if she adds "you're too good a friend".
Categorisation into the Friend Zone happens within minutes of first meeting. There's no way out of that box.