I have never had the opportunity to experience any flirting and as a result have no idea how to “give hints” I want to be chased.

Should I run up to them and pinch them and run off again?

Mary

I too have pursued and been burned, if you’re a guy, it’ll probably happen one time or another. You’re stuck in the position you’re in because he’s not fulfilling his role in the pursuit. As the female in the pursuit, you want him to pursue you and not the other way around.

A lot of what Mr. Ethical Slut suggests plays directly into pursuit theory. What you need to do is let him know that it’s okay to pursue because the chance of success is high. You can make a comment when he holds your hand, or even suggest that you hang out separately. A simple kiss on the cheek and a, “call me tomorrow,” can work wonders for this type of situation. Pepper your conversations with invitations to call you, get together, etc. That’s your role in the pursuit.

Just be careful of how long you lay out invitations. If he’s not picked up on your first few invitations, he probably won’t. Though the uncertainty of the situation makes it all the more enticing, there will be a time where it becomes tiring. Ultimately, if he’s not willing or able to come out of his shell and make a move, he’s probably not the right one for you.

Best of luck!

Since I do not know the specifics and history of your relationship with your friend, it is a little difficult to give you advice on what specific thing to do. However, I can give you a guide and ultimately, it is up to you to use your better judgment and do what feels right. So with that said, here are some things that popped out at me:

“Not that I am afraid of getting rejected, but rather of pushing him away”
First of all, I wonder how close the two of you are. If you have a strong friendship than having intimate talks as these can be an opportunity to strengthen your relationship. I think it takes a lot of courage and trust to see friendships all the way through. If he is meant to be in your life (either as friend or boyfriend), he should be able to talk to you about sensitive topics.

“I’m not sure if a girl making the first move wouldn’t threaten his role as the man and completely turn him off.”
Well, you know him better than I do, so you would know whether making a move would threaten his manhood. I don’t think making a first move should be equated with being a man, however in your situation, I do agree that he should probably do most of the pursuing. Part of the attraction for guys is the pursuit but it’s not the only thing. Also, in general, if a guy likes you that much, he will pursue.
On a side note, You might also want to ask yourself if such a masculine man who is strict with gender roles is something that you value.

“I want a chance to try and make him happy.”
It sounds like you really like him. So do you think you may be interested in him more than he is interested in you?
In the past, when I was infatuated with someone, I would interpret every look and gesture as a sign of interest. However, I later found out that she was not interested in me, so it was all a projection of my wishes for her to like me. So hopefully this example can help you see if you like him as much as he likes you.

“If there is a good way to tell him that and to find out his own intentions, please let me know.”
So I understand that you don’t want to make a first move, which I completely honor. I do want to point out that there are things that you can do that are not technically making the moves. The next time he gives you that “look” or hold your hand, you can give him positive feedback like a smile or your “look” back. If he flirts, flirt back. I’m sure you are smart enough and know him well enough to understand what signals he will and will not get. If you want to up it a notch, you can tell him, “It’s nice when you hold my hand.” If you want to see what his intentions are, then you can ask him, “So when you look at me that way, what are you thinking?” or “I’ve noticed that you’ve been holding my hand a lot recently . . .”
Anyway, those are some suggestions and you should definitely take it with a grain of salt. Apply them specifically to your situation and adjust them as you see fit.