Question

What should you do?

Say something like this.

"A, let's go out to dinner on Saturday night. Are you free?"

And she says either yes or no. If she says no, ask about Friday or Sunday or whatever. If you get three No's, forget it. If you don't, then it's just a scheduling issue (by the way, the three number is fluid; just gauge it by interest, enthusiasm, or lack thereof).

When you get to yes, say, "I want this to be a date. I really like you."

She says something like this.
a) I'd love to. I was hoping you'd make a move.
or
b) I'm sorry. I really just want to be friends. I hope I didn't lead you on.

Note – get agreement on the dinner before telling her you'd like for it to be a date. This is not bait and switch. Rather, it is giving her (and you) a more gracious exit if she gives you three No's and it's clear that she isn't interested. But you do need to say that second piece, about wanting it to be a date, as not everyone can pick up subtle signals.

In short,

(1) You ask to spend time together. Friends spend time together. However, you are asking for dinner on an obvious date night, so that should be a clue to her. If her answer is going to be (b), she's already clued in that something is up and, if she is not interested, she may make the (b) speech then.
(2) You persist if the response is negative, but only a little bit. You attempt to be accommodating if it's truly just a scheduling conflict, but you back off if you're getting roadblocks. You don't overdo it. You don't go all stalker-y.
(3) If an agreement is reached, you make it clear that you want it to be a date. You also make it clear that you really like her (if there is any interest at all, she will love hearing that. If she's been with a lot of jerks, then it's likely that many of them didn't tell her that, or didn't tell her that too often).
(4) You are giving her the opportunity to back out if she was uninterested in you that way and not clued in by the time you got to the third step.

Oh, and

(5) If she says (b), then be gracious and say that you're sorry you bothered her and let that be the end of it. Warning: you may lose her as a friend, despite how kind you've been. That happens; people feel awkward. But you'll be able to hold your head high and will also be out of the friend zone rut of wanting but not doing. And if she says yes, well, make it a nice dinner but don't lay a million expectations on it. It's dinner with a lovely date. Wait until at least your third date to start discussing china patterns and baby names.

PS I can practically guarantee that at least one person will tell you to treat her like dirt and that that will get you an in with her. If I were her, I'd be appalled, and angry at such treatment from someone considered to be a friend. You may strike out with her but you say you've got a boatload of female friends. If you start acting like a dick, they will notice and, if it doesn't happen with this girl, you may find you've poisoned the well with all of them. So be aware that, like it or not, there's a bit of an audience. You don't need to play to them, but do be aware that if you're a Grade A asshole, she will likely tell her pals.

Tell her you are an ugly scumbag who will cheat on her, and that you want every possible disease she has picked up from all her cheating partners, and she won't believe you, but love you for your honesty...because, like most young and pretty people, she has no idea of what she has, and likely values herself for qualities she only wishes she had, that is for the ideals she holds dear which usually amount to nothing...

Friendship seldoms turns to love, and love never turns to friendship... If you want her then be bold... A woman in her prime is like a flower to the bee, sharing her nectar, and seeking to please... If you have no honor then you are no man, but if you are a man, then offer her your honor or leave her alone...

ahh... courage would be a wonderful thing. As a prefect in secondary school I once faced down a girl wielding a flick knife (long story, I still have a scar on my hand...) and your solution still scares me (Harry Potter: "I think I'd take the dragon now. " )

I would NEVER act like a jerk to impress her, and anyone who offered me that advice would be laughed at. At best.

I have to admit, intellectually I know you're right, but emotionally I'm hiding under my bed listening to Taking Back Sunday and having a panic attack.

They should teach this stuff in schools...

Points for the Harry Potter reference.

I'd recommend broaching the subject in a general way first, seeing what kind of response you get.

Don't act like a jerk, yes. Good for you for rejecting that outright.

That's why we're here.

I know, I know, it's scary. A lot is at stake.

But it never goes anywhere if you do nothing, yes?

One thing that has been suggested here several times, is practice. Not necessarily practice asking a woman out, but just practice talking to people. And I realize you may be fine with talking to everyone but her, but hear me out. It may help to do some more talking to, well, anyone. Your corner grocer. The neighborhood dog walker. The waitress at the doughnut shop. Whoever. The beauty of those encounters is that they're not fraught with meaning. They are - how's it going? Or, is your dog friendly? Or, what are the specials?

And then talk to this gal as if you were asking her what the specials are.

Uh, don't actually ask her what the specials are.

Just clarifying that.

She's your friend, yes? So I get the feeling that if it's a no, she's not gonna be nasty about it. It will suck if it's a no, but without doing anything, it's an automatic no. At least by trying, you've got a greater than zero percent chance of a yes.

I can talk to her, we talk all the time. I could broach any subject with her, except my feelings. And yes, we're friends. And we share pretty much all our friends. Damn, this could get awkward...

You have no idea how good it feels to be able to talk about this (figuratively speaking...)

Who doesn't love Harry Potter? It's like the Bible, except for hormonal teens

There are ways to broach the subject of your feelings. It's tough though, and so specific to a given situation (what you guys usually talk about, who you know, how well you know each other's expressions/ body language, etc., etc.) that it's really hard to give you advice on how to do it.

The idea though is to bring it up in such a way that if the initial reaction is negative, you can then just move on without spelling everything out.

If you bring it up overtly, and she says "no," where do you go from there?

Is that completely fine with you? (Not as in you'd act out or be mad, but are you truly OK with being friends with her if romance is completely out of the picture?)

I'd live. I'd rather be her friend than not know her at all.

Hmmm.

On the one hand, that makes me say "go for it!"

If the downside is not that down, and the upside is very up, then why not?

However, I'm not sure if I believe you.

"I'd rather be her friend than not know her at all," sounds like it could be a recipe for extreme moroseness and not moving on to other people with whom you might have a chance.

On the third hand (OK so I'm not being completely biologically accurate here), the "moving on" bit indicates finding out what the possibilities are so that you can move on if the answer is "no." (And if the answer is "yes," great!)

So, all in all, I'm not sure what to advise from what you've said so far. (I know, I'm so helpful, sorry.)

What is your current thinking?

I like to think I wouldn't mope too much, but who knows?

My big fear is that the ensuing awkwardness would destroy our friendship.

Frankly, it's hard to say this but I'm afraid of the potential consequences of telling her how I feel... is that stupid?

It's not completely stupid, no.

The tricky part is, it might be! I don't think we can know from here.

But it can definitely become awkward and friendship-damaging if it turns out that one person -- and just one -- harbors romantic feelings.

hmm... yes, I take your point.

Maybe I should hold off and try to see if I can guage her feelings before making a move?

If you can see a way to do so, I'd recommend it, I think.

Thanks! I'll do my best. I guess this is where knowing her for so long will be useful

I suggest that you try to find a copy of the American TV show The Pickup Artist or possibly read one of this guy's books.

Not to become a pickup artist, per se, but because this guy has a very interesting take on the psychology of dating.

While you're at it, get a copy of Predictably Irrational.

Ever hear of Gretzky's line - you miss 100% of the shots you don't take?

Well one thing is for sure - if you don't ask you ain't gonna get. If you would like to date her, why not ask? Maybe she will say yes or maybe she won't - maybe it will work or maybe it won't - one thing is for sure - if you don't ask it will be "no" and it will not work.

True. And yes, I know the line.

I guess I hadn't looked at it that way