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Great points! However, does this make it look like I'm trying too hard, or could I be coming on too thick asking such things so directly?
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Not from my exprerience. I think it shows genuine intrest in who she really is. Which you should have by the way, don't fake it. People are so used to fluff talk about nothing that big questions tend to make them perk up and think "hey this guy is really intrested in me". Try to stay possitive, you can find out her fears and dark secrets when your relationship is solid enough to handle them. Don't overwhelm her with 20 questions either, just pay attention, people give openings for a deep conversation all the time.
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I don't mean to sound fake, and I'm not really, but I've read online that the best approach is "cocky+funny", and this is what I tried at first. My friend told me I came across as a total asshole and girls shouldn't be treated this way, so I did a 180 degree turn around on my "approach" and became a total nice guy. This has worked so far only because she has just as much interest, I think..
And I certainly hope its not some asshole that gets in for a few days then gets out. If that is really the case for college, that's quite sad (I wouldn't know too much about this area, hehe).
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confident / funny.
There is debate over the meaning of confidence though. To me it's being comfortable in your own skin. Some people come off as assholes because they act like: "Look! I am better then everyone else". If you really have confidence you would not need to measure yourself up against other people. I hope that makes some sort of sense.
The problem with being a nice guy is that you are walking a thin line. Women generally don't like men who are pushovers or who will put themselves at a lower level then them. What most girls seem to really want is respect and a little bit of gallantry. The other problem with being a nice guy is that it's hard to be sexual. When you do make a move you run the risk of looking insincere - as if you are putting on a nice guy act to get in her pants. I hope you get what I mean.
Next.
I think you gota start making headway with getting closer to her. So far the signs point to the fact that she is comfortable with you but is she attracted to you? Take every oportunity you can to touch her, but don't just reach with your limbs, use your whole body. When you take her hand step closer. Instead of leaning in to wisper / hear better move your whole body towards her. When you make contact, make sure that it's sexualy charged. Hold her hand a little longer then usual. Touch her shoulder and look into her eyes. There are many oportunities for touch. For example next time you open a door for her put your hand on the small of her back and usher her in.
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Hmm, being a total noobie, I assume an 'intimate' moment would be something like both staring into each other's eyes and feeling like kissing, or something like that. Well, I don't think I've come across one yet, but I think wouldn't preclude it if I tried....
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That's too bad, try to create those moments. The only way to do that is to put a sexual vibe into your encounter. Don't be appologetic about it. You know what you want and she knows it as well. There is no need to try to trick her or yourself into it. You want her as your girl, you want her as a lover.
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Wait, if I *PAY* for these its NOT a date? I'm just a 'friend'?? I thought its the other way around: you pay for your date, and don't pay for your friend
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You are on a date ONLY after you've made out with her. Before that you are still trying to figure out where you stand. Now this is my opinion and you don't have to agree with me but why would you give something to someone? You give because you either (a) wan't something in return or (b) reward. If you go with (a), arn't you pretty much trying to buy her out? To me, that seems low and dishonest. You can justify it by saying that it's an attempt to be nice, but I think thats pretty weak as well, there are better ways to show you are a nice guy.
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Hmm ok. I'll do it sometime but only after a few more dates because I don't want to scare her away...
And what does making a move comprise? Like, putting my arms around her, or going in for a kiss? Or do you mean like, actually asking her 'hey lets start dating'???
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A kiss (not a peck). Make it on your next date. I think she has already decided if she wants you or not, my advice is to find out now. Don't ask, reach out and kiss her.
Best of luck to you.