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Spoilered for wall-of-text-written-because-I-think-too-much:
There's this girl who floats on the periphery of my friend group who I've had a small crush on for two-odd years. Nothing debilitating, just one of those things where both of us could tell there was an attraction, but one of us was always dating someone else so we just flirted a little bit with the mutual understanding that nothing would come of it. We're remained friends and see each other all the time, but we're not too close and don't know each other THAT well.
We both ended up single a few months ago, and even though our recourse was obvious, for some reason we both just froze. I found that my small crush on her was a lot bigger than I thought it was, and we both seemed to realize that we're actually super shy and awkward around each other when we're both available. I'm not normally nervous about the dating thing, but I really like this girl on pretty much every level and don't want to risk losing her as a friend over this. That's the reasoning that was fueling my pussyfooting until about a week ago, when I finally summoned the cajones to just go ahead and ask her out. She agreed (!), and suggested we go on a honest-to-goodness first date Monday night.
Here's the situation: I've never really transferred out of a friendship and into a relationship before. The one time I tried, well, it ended badly and I'm still dealing with the baggage from it. I honestly don't know what I should be doing on this kind of date, as it's a completely different beast than the sort of first dates where you're just trying to get to know each other from scratch, and don't stand to lose a friendship to the "awkward drift" if things fail to work out.
Like I've indicated, this girl is both capable of being very shy and very flirty. Right now, she's being very shy (but has been warming up again since I asked her out) - probably because she likes me but isn't sure if I'm her type. She's certainly not leaping into my arms and is pretty insistent on going on a date first (rather than the normal college hook up, date later mentality), which is kind of putting me at a loss as to what to do. She suggested dinner or coffee, but both options seem kind of impersonal and inappropriate, seeing as we've already been regularly seeing each other at lunch/dinner and hanging out after classes and running into each other at parties for the last two years. She's still 20, so anything alcohol related is out - not that this would be a good place to start anyway. And honestly, I want to do something interesting, because this girl is really quite pretty and gets asked out by a lot of guys, and I feel I need to distinguish myself a bit.
I know she likes me - she doesn't get this shy with most guys, nor will she agree to a date with many of them - and that I'm already halfway there. I just need a good way to rebreak the ice and get her comfortable with the idea of being more than a friend; I know I can't come on too strong (it would make her uncomfortable), but I can't be weak and forgettable either. I think I need to be convincing, if that's the right word for it, and I'm afraid that I'll get the dreaded "let's just stay friends" after an innocuous and lackluster coffee/dinner date. Anything more interesting and fun that we could do? Any tips on how I can chip away at her shyness and get a second date (at the very least :P) out of her? Am I thinking too much about this?
tl;dr: Asked out a girl who's long been a friend of mine, and while things look promising she's locked herself behind a wall of bashfulness and seems to be sizing me up for chemistry. We don't know each other THAT well, but well enough that a coffee/dinner date would be a a boring and silly place to start. Any other casual date ideas that I can use to show her a good time and break the ice?