You didn’t ask for an estimate of the situation, but may I suggest that maybe you pal is feeling the same uncertainty as you do. As a man, I’ve had several occasions where I was with a girl and wasn’t really sure whether she would be open for some more romantic developments. So you sit there in the movie or the theatre and are both wondering whether you should touch hands or not. Only afterwards I found out that she was misreading my signals in the same way I was.
Okay, I may be particularly dim-witted in this respect, but it may wel be your wonderful friend doesn’t have much of an intuition in this respect, either. With some girls it seems harder to cross the line from pals to possible romantic interests. It has to do with body language; if you are the type of girl who isn’t in the habit of friendly touching people or standing or leaning close, but instead sit upright and keep physical distance, you may send an unconscious signal: stay off. Particularly if the guy values your friendship (and I get the impression that he really does), he feels in the same bind as you do.
Now for your question: what to do? Apparently you are not afraid for a negative reaction (given your hypothetical MIB example), which is good. You are only afraid to lose the friendship. I would be very surprised if a man would react in the manner you fear. In the past I’ve had some signals of female friends who at the time were interested while I wasn’t. One even asked, during a conversation about my previous girlfriend, whether it would be possible for me to fall in love with her, to which I replied that I didn’t see that at the moment (she was good-looking, but a really different type of girl than the one still on my mind). In all cases I still continued to see them without any strange feelings.
For men it is mostly flattering if a woman is interested. Only the ‘jock’-type of men would be harsh or cruel about it, and I don’t think your guy is like that at all. The other way around it is more difficult, as I’ve found out to my regret. Women may feel a bit threatened if a man (subtly) expresses an interest for more than friendship. I can’t blame them, but I’m still sorry of having in this way lost touch with some people. This may explain the reluctance of your friend. (Rereading your OP makes me notice that your friend is much more sensitive than most, so that makes it clear why you are afraid to go too far too quickly)
Now for what you can do about it. You may try bringing up the subject more subtly: what does he look for in a woman (or have you already had that conversation?). You may try to touch him: there should be opportunities for a quick gentle touch when he offers you your drink or so. You may try to sit closer to him, or even lean your head on his shoulder, to show you are comfortable with his physical presence. Of course these are still subtle messages, but they may help him to gather courage if he needs it. They also make it possible for you to estimate his reaction. If you both feel comfortable sitting next to each other, you leaning against him, it is quite natural to put your arm around his waist or even for you to grab his arm and put it around yours. If he really isn’t interested, at some point he will show reluctance. Then you may have your answer, without having the awkwardness of a conscious and open refusal. But do not be too quick to assume that there is reluctance! Some of it may just be involuntary reaction because you aren’t yet so close. If it is however a case of slowly but consciously withdrawing his hand, I guess he is not interested.
Does all this make any sense to you? Since I’m no Casanova either, you may want to listen to others (including the earlier posters) too, who may have better (and possible contradictory) advice.
Alternatively you can introduce him to the wonders of SDMB and let him ‘accidently’ find this thread. Then see whether he chimes in with an ‘I know exactly what you are talking about. There is this girl I’m dating for a year…’
:eek: Say, you don’t live over here, do you? There is this girl I’m seeing for a while now… (just kidding, I’ve gone in the handholding stage already)