Let's take a moment out from the close examination of Macaulay's life to look at him at him. Like, really look at the guy. There's no doubt that with that blond hair and eternally boyish face, he's a pretty handsome kinda man. As long as he's not trying to grow his scraggly blond beard, he could date a girl half his age and no-one would think twice.
On the other hand, if you look at his eyes, you'll notice that you really don't need to be perfect to get into Hollywood. One of his eyes - his right, if you can't quite tell - is actually bigger than the other one. He covers it well with sunglasses and that wide-eyed look he perfected as Kevin McCallister, but he has said in the past that it's a part of him he wishes he could change.