Let's see how to tell you this... Some weeks ago I attended an art exhibition where I met an old friend from college I had lost track of. Let's call her Laura. Soon after that, she invited me to his birthday party and we and her friends had a blast. Over time, I have noticed her IM'ing me with cute phrases, emoticons and stuff, but the moment I realized Laura wants something else from me was when she sent me some songs (we have more or less similar tastes in music and have shared some) with highly suggestive lyrics. Well, as an aspie I must be the most distracted man in the world regarding romantic signals, but I am certainly not stupid.
Me being the one that always thought having such bad luck in sentimental affairs that not even a fly would stick to me am suddenly faced with a situation where she evidently wants to go beyond a friends relationship, or so it seems to me. It may as well be that she always had a crush on me at college and I never corresponded her, who knows. Plus, she's about five years older than me and it's somewhat tomboyish in appearance (she's not into long hair, I have longer hair than she does and I'm talking crew-cut), plus... well, i'm not exactly looking for Jessica Alba, but the selfish part of my conscience keeps muttering if this is as good as this is gonna get for me, while still longing perhaps unrealistically for "banging hot chicks" I'll never have access to due to my introverted personality. Time to "get over it" perhaps?
Anyways, I do appreciate her very much and wish to keep being his close friend for life. But I'm not sure if I really want to go beyond that, yes, even if I am in a "You're always complaining you never get a date and now you finally get one, what the hell is wrong with you?" situation. Last time I had an ongoing romance was in elementary school, imagine that. Plus, there's the fact that we live in a society where men are expected to make the first move, not women... chauvinism, I know, but that's how it's always been.
Whatever the case, I arranged a date with her tomorrow. Nothing too fancy, kind of a coffee talk, but I definitely need to find out what she's up to.
And if I think it's better to remain just friends, how to tell her so without hurting her feelings?
And for the record, we both are in our early thirties, so I'll appreciate advice from people here that are closer to my age range (perspectives change with age, you know - no offense to the younger ones)
Thanks to all in advance 
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"Many people would rather die than think; in fact, most do." - Bertrand Russell