I know all about the friend zone etc., but in my case where both myself and my good friend are somewhat shy people who have never been in a meaningful relationship, how can I explain my feelings for her? We go out on "dates" all the time, and I've spent more money than I would've liked to already on her, so that's not a valid way to win her affection.
When you go out, are you alone or with other friends?
Otherwise just do activities lovers would do. This will create the right mood to start behaving like lovers, even if you did not say it plainly. Instead of asking her out, just go out with her,...
That's my problem I do those things alone already but want to be more intimate.
Try going with friends one time, if she really likes you most likely see it. While on the date, when the time feels right to you, tell her how you feel, it might work that way. Try it, intimate otoko!
Then why not talking about relationships, love, and this kind of topics? At least you can feel her mood about this kind of things. You could watch together movies that set you in the right mood also,...
Flirt with her, and watch her reaction. After a couple weeks like that, tell her you really like her and want to date her.
Wait, wait, wait. You take this girl out often, pay for her all the time, and you're NOT already a couple? What the hell are you thinking! If you're not locking lips with this girl you're nothing but her stooge.