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[Pathos v2]

Don't big it up to yourself or to her.

Just say, "I like you a lot. Wanna go out sometime maybe?" Say it offhandly, don't make it seem like it's overly important and most of all don't try grasping at anything if she tells you it's not reciprocated. It doesn't really matter where you say it, although walking her back home is probably the best idea. Try to do it close to her home so you don't have to have an overly long walk of awkwardness if you mess up, that can be the worst thing.

Believe me when I say the absolute worst thing you can do is make it seem like your attraction to her is a big thing. A level head is an attractive trait.

[Captain Mayday]

So.. not on public transport, then.

Other then offering to walk her back, anything else?

Well, the problem as I see it is that you want to ask her whether she wants to change your relationship, while ensuring that if she says no, your relationship remains fully intact.
In all honesty, what you want is not possible. Not just because she'll know you were interested in her, but because you'll know she knows that, and that she turned you down.

As for location, it's not as important as timing. You should probably ask her before you need to part ways for the day. Regardless of the answer, it'll be uncomfortable if she gives you her answer and then you just need to hang out for ages.

So really you'll need to do this in a way to allow you both to save face should she reject you, as she's free to do. So I suggest asking her to consider the idea of going out with you. Something like the following, although in your own words.
"Hey <girlname>, can I ask you a serious question?" - nobody ever says no to this. It also lets her know you're not just joking around.
"I want you to consider this a while before answering. We've known each other a long time, and I like to think we're good friends, but it occurred to me that it might be worthwhile seeing if we could be something more than that. I'd like you to think about whether you'd be interested in seeing where that might go."

Effectively, you're making her consider you as a suitor rather than just a friend.
Not entirely depending on her certainty, she will most likely answer right away, or will take you up on your offer of thinking about it.
Regardless of her answer, you need to have an answer prepared.
If she's interested, ask her if she'd like to go out on a date, and know where you'd want to take her.
If she isn't, suck it up and say something like "Well... it was just a thought." and play it off casually. If she needed time to think about it, you should thank her for considering it.

[Kaiser Reinhard]

I've already spent a full year thinking about it. I'll accept whatever decision she makes, as long as she makes a decision. I am quite confident that her turning me down won't affect my relationship with her too much as long has she herself is fine with me liking her.

It's also why I'm asking for help as to how I'm going to confess to her. I want to be sincere, yet at the same time I don't want it to seem like rejection will affect me too much. I want to be in an environment where both she and I are relaxed, so she can respond however she likes with no pressure, I can say what I feel without anyone panicking and if it goes badly I can reassure her that it's fine and I'm perfectly capable of moving on from it and just being good friends with her.

What I've had in mind is asking if she would consider entering a relationship with me, while admitting that I'd come to like her a lot. If she returns my feelings, great, if not then I just reassure her that it's fine and that I'm glad I can still have her as a friend, trying to make sure she is fine with knowing how I felt about her.

I also don't want to mention anything about how close we are or how long we've known each other, I don't want to make it seem like rejected how I feel would also constitute rejecting our friendship.

[Captain Mayday]

Seems like you already understand how it has to be handled, then. There's little more you can gain from asking on the internet. All that's really left is for you to seize the moment and just... do it.

[Keita]

Best way to let some one know? Tell them.

You've got all you want to tell her figured out, that you like her and wish to pursuer a relationship, you want her to not feel pressured into it and that you are ok with a no. Tell her, when you ask her out, say something along the lines of:"...and if you don't want to to go out, that's fine."

But as Mayday says, go for it.

[Kaiser Reinhard]

Just go for it, huh? Yeah, already decided that. Now I just have to figure out the specifics.

[GamerKnight]

Been there. I know this chick, had a massive crush on her a couple of years back, didn't tell her or anything, and know she goes out with guys 5 years older than her and she drinks like hell at parties. Don't really know her anymore. Just go for it, before you lose the chance forever.

[DJ]

Just go for it, huh? Yeah, already decided that. Now I just have to figure out the specifics.

The more you plan, the worse your chances.

[GlyphGryph]

Just go for it, huh? Yeah, already decided that. Now I just have to figure out the specifics.

The more you plan, the worse your chances.

Considering you were going on earlier describing her practically setting you up for the opportunity, you may have already blown your best chances. There's a good chance that the longer you wait, the worse it will be - she's probably noticed something, and if she has, her opinion of you isn't going to be improved by the fact that you can't be bothered to let her know.

In the absence of a good reason otherwise, the time is now, and you've got plenty of good advice on how and where to do it. It doesn't need to be as blatant as has been stated sometimes in the thread, but you need to do something. Have you at least tried to hold her hand or something yet?

[Kaiser Reinhard]

Nope. Only physical contact I have with her is occasionally prodding/petting her arm in conversation (though when I pet her I make it look like I'm doing it mockingly), high-fiving her which happens almost every time we go out and agree on an opinion we feel proud of, and her grabbing my hand for a second to get my attention and drag me to something interesting nearby the last time we went out.

[GlyphGryph]

So start subtle, see is she's responsive. Play the game if she wants, be blatant if she wants, but start doing something asap.

You don't have to move fast, but you do have to start moving.

[Kaiser Reinhard]

How? Do you mean to say I should just grab her hand?

[GlyphGryph]

Well, no, be smooth about it if you can.

Like people have said, her territory or neutral territory, not in a situation where she'll feel pressure, preferably a subdued situation after one a bit more active. I mean, I'm no cassanova, but I've found when with friends that I'd like to become more than friends, talking a bit about how you've just had a pretty good time, and your glad it was with them, and offering your hand is pretty good. Plausibly accidental contact that you let linger a bit is even more risk free and can be exciting, but you've got to have some confidence for that, and not read too much into a failure, and not do it enough that it gets creepy, so maybe best avoided in this situation... And even if you aren't comfortable with the hand thing, you can start by talking, offer a compliment, talk a bit about emotions, ask her how she feels. Don't be afraid to step slowly, just don't turn back unless you've got a reason to.

But the execution doesn't need to be perfect, and you've had plenty of other good bits of advice on how to approach it in this thread, some of it probably much better than mine... but, generally, I'd stay start small, and progress if she feels comfortable. But once you've started, don't back out because YOU feel uncomfortable - if she's being receptive, take the lead.

Since its all based on how she reacts, a plan won't really help you beyond planning an activity together after which you can relax (lounging on a couch, walking to her house, etc etc)

[Keita]

Ninja'd

But a good ninja =P

[GlyphGryph]

Also, don't admit right away how long you've been crushing on her. That can come later. For now, remember what's important is that you are into her NOW and you want her to know it NOW because you'd like it if you were interested in it NOW.

If you come right out and tell her you've been crushing on her for a year, errr... just don't do it. I mean, if it comes up, don't try to lie or anything, but don't steer the conversation in that direction. You want it to be about her and your feelings for her and hopefully her feelings for you, and talking about stuff like that changes the focus to being all about you and your needs, which is a bad way to start things off. As the conversation gets going, you might both nostalge a bit, but that will come naturally if it comes.