my plan was to get close to him by increasing the level of intimacy in our conversations

Visitor's Question from a 16-20 year old Female
I've been having feelings for this friend of mine for a while, and I'm not quite sure on what to do about it. He is so smart and really deep, but also the type of person the more you get to know, the more misterious they come off, in fact, he seems more and more troubled as we go forward in the conversation, and though that doesn't intimidate me, I feel that this is only the tip of the iceberg.
I have to say that telling him how I feel is not an option, I know for a fact that he won't even consider dating a girl unless he's the one crushing on her, so I have to draw his attention to me without letting him know I'm doing it willingly.
I'm stuck, and completely clueless on what to do next, since my plan was to get close to him by increasing the level of intimacy in our conversations, but when asking him personal questions all I've managed to get out of him is lots of "It's complicated", and I don't think he's very intrested on hearing about my personal life either. Basically I don't know how to get him to trust me enough to open up (you guys told somebody once to ask her introvert crush about his hobbies. should I try that?).
I really like him and I'm not ready to give up on him, should I stay with my plan or try a different approach?, and if so, what do you suggest?. Thank you. Advice
You are doing fine so far.

He is stonewalling you when he says something is "complicated." All that means is that he is too shy to talk about it.

So, keep the questions simple... asking him about his hobbies is a good idea as you suggested. We have tips about what to talk about at:

Hopefully some of those tips will help!

-- from George
One of Your Friendly Advisors at

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