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[Il Palazzo]

Ugh. Dude, this is no rocket science. She's not interviewing you for a job, nor is she an examination comitee. You don't have to ace the test by chosing perfect words and perfect situation - most likely, she already likes you "like that", and is probably just as anxious about the whole thing as you are, unsure if you actually feel the same about her or not. She knows you well enough to like you for being the person that you are, that she's known for so many years already, and not for what you'll say to her on that one particular moment, or how you'll do it.
And I'd say don't be afraid of saying weird things, if you feel them. She is just as much of an inexperienced teenager as you are, and won't look down on you for any faux-pas that you might commit.
Just blurt it out, without pretending that you're somebody else. Ums, ehs, stutter, unnatural voice, red ears, losing eye contact, and all that won't matter. She'll appreciate your honesty and be glad that you've made the first step, however ungainly it might be. The rest won't matter.

[Greep]

Gotta agree here.  In this situation, other than feeling like an idiot for approximately 3 seconds, you don't have much to lose.  TBH, the way you've described her she's at the very least "kinda shy", so the more bashful you sound asking her would probably make her feel better.  So I wouldn't even plan what to say, just go blurt it out.

And yeah, at this age, you really need to act now.  By the time college is in either of your immediate mindsets (You're 16 so we're talking like a handful of months, or even too late really) you can pretty much kiss goodbye any chance at a long term relationship.  Even if you're going to the same college even, college just muddles things up with very new relationships, so now's the time.  I'm guessing junior prom is done by now which would've been the perfect time really (), but you really don't want to wait for senior prom, especially if it's so expensive you can't afford it like I couldn't lol.

[SeaBee]

The one thing you don't want to do is nothing.

Don't plan so much! Just be honest. She's your friend, right? The last thing you need to do is over-think this thing. You'll come across as unnatural and ... well, odd, since it'll be clear to anyone close to you that you've been planning for some time.

Want a scenario? Here you go:

1. Meet up with her in some comfortable and neutral location
2. Ask her if she'd like to go on a date (or whatever the appropriate term is for young lovers these days)
3. Do not overreact if she says yes OR no, keep calm and friendly

But do it soon. I don't want to pressure you, but if you don't act fast you'll end up regretting it for the rest of your life. Better to be rejected than to never know.

TL;DR: Do not think, act. Remain friendly and calm throughout.

[GamerKnight]

You asked ages ago, Kaiser Reinhard, have you actually done anything yet?

[inteuniso]

I'm intrigued by this, mainly because I have no childhood friends. How goes it Kaiser?

[Kaiser Reinhard]

Nope. Currently I'm crushed with a massive workload because pre-u courses are grueling as hell. The little time I had last weekend was spent taking care of my little sister and doing assignments.

I'd like to ask her out again this weekend, though I'm actually very shy about it. Most of the time when I ask her for anything more than a meal I say that I'm going to do something and ask her if she wants to follow along. It worked last time, at least.

[MetalSlimeHunt]

Then it sounds like you are just taking her with you as an afterthought, which is bad. Ask her to do somthing with you, specifically. And if she asks you if that's to be seen as a date, say yes.

[Jopax]

I have a similar problem myself, and one of the biggest difficulties is making that move since i have no idea what i should be doing at that point XD
And one of the funniest problems, atleast to me is how hard it is to call her, i get incredibly anxious for some reason, but when i'm with her everything seems to be going smoothly :/

[Kaiser Reinhard]

Then it sounds like you are just taking her with you as an afterthought, which is bad. Ask her to do somthing with you, specifically. And if she asks you if that's to be seen as a date, say yes.

I guess so. I'm always trying to seem like it's not too important to me, both to deal with my own anxiety and so being rejected feels much less awkward.

I have a similar problem myself, and one of the biggest difficulties is making that move since i have no idea what i should be doing at that point XD
And one of the funniest problems, atleast to me is how hard it is to call her, i get incredibly anxious for some reason, but when i'm with her everything seems to be going smoothly :/

Yeah, I know. It's the same for me, I'm anxious when I try to contact her, but when I'm with her in person I'm fine, probably because I can read her body language and such.

[MetalSlimeHunt]

Then it sounds like you are just taking her with you as an afterthought, which is bad. Ask her to do somthing with you, specifically. And if she asks you if that's to be seen as a date, say yes.

I guess so. I'm always trying to seem like it's not too important to me, both to deal with my own anxiety and so being rejected feels much less awkward.

That is a very bad course of action. Don't be obsessive or anything, but if you create a feeling of unimportance then she will (obviously) believe you consider your friendship to be unimportant to you. If you value your friendship (or possibly more) to her, then act like you value it. Not to mention that people have a high tendency to internalize facades. If you act like its unimportant to you, eventually it will be unimportant to you.

[Kaiser Reinhard]

Oh, damn. Suppose I should just be more relaxed and open, in that case,

[SeaBee]

Oh, damn. Suppose I should just be more relaxed and open, in that case,

This is wisdom.

[Keita]

Oh, damn. Suppose I should just be more relaxed and open, in that case,

This is wisdom.

And a very good course of action.

[GamerKnight]

Good luck.

[Joshua IX]

Please please please just go ahead and tell her. I did what you've been doing - was nervous, anxious, kept on waiting - with my current girlfriend. When I eventually got the courage to ask her out, she said yes straight away, and that she'd liked me for ages.

I kick myself at all thsoe months I wasted not being with her her because I wasn't confident enough to tell her how I felt.

If you're good friends you'll survive it, and if you are right for each other it'll happen.

Best of luck!