So...
Go on and express your LOVE:)

Afterall, the downside of it is that you might get rejected. But the upside of it is that you might get accepted!:P By not asking her out, you'd never get her (and you'll never know if she was waiting for you to initiate all along).

Ever seen couples walking on the streets? Aren't they mostly a gorgeous lady and an average looking (if not worse) guy? The myth goes like this. A super handsome and hot guy would set his expectations higher because he reckons he's got the quality and the ability to get prettier ladies. Meanwhile, the not-so-good-looking guys would think that they have got nothing to lose by asking these ladies out, and there they've got it!

Of course, gorgeous ladies might set higher expectations and might even reject these guys. But the whole point of this is that ladies always wish for guys who initiate things. It's all about taking the first step. Whether love blossoms after that is another thing.

Also bearing in mind that guys can get married at any age they want to and there wouldn't be a problem with that, but ladies would hopefully want to get married off before the 30th mark. Sooner or later, single ladies have to lower the expectations of their prospective husband to settle down (not all ladies look for wealth and looks; most look for good qualities eg. caring, loving..).

If you're afraid of being rejected, or perhaps the awkwardness after that, worse still, the loss of a friend, then look at it this way. How long do you plan on staring at that person in secret for? Isn't there gonna be a day when you'd realise it's not gonna happen between you guys and you should really move on? To realise that many years later, why not just get it over and done with now? By asking now, you would know how she feels. You might regret asking, because you feel like you just lost a friend because of that. But many years later, you will actually look back and not regret this decision, because at least you've spoken up and you got an answer. You would prolly be thankful that she helped you move on with your life.

Now imagine if you never ask, then many years later, you realise she was waiting for you to initiate but you never did, would you regret now? Yes. But what can you do now? Nothing? Because she would prolly have moved on with her life.

So do you want to regret now but realise your decision was right in the future, or regret for the rest of your life that you never had the courage to ask?

With regards to the awkwardness, doesn't that subside as years go by? You might lose a friend now, but you might gain her back in the future. Same with relationships, when couples break up, it's almost never possible to be friends again. There would always be this awkwardness in between, even for couples who break up amicably, but I strongly believe it will subside. Many years later, you guys might even look back and laugh at things you guys used to do together. I know I did that.

Remember, you'll never know if you never ask.:)