This guy you describe sounds very much like me. Maybe one thing you could do is find out whether there is a specific reason for his emotional detachment that is preventing him from being in a new relationship. For me, that issue is a deep hatred/loathing of the flaky nature that most people seem to have. Also, it sounds to me that he isn’t sure whether or not he has feelings for you or not, so if you want him to like you, you’ll have to work at convincing him of that, by being there for him and making sure he has fun when he is with you. I would bet you that he wants you to convince him of this. That may be easier to do if you can be extraverted and spontaneous, light of heart and FUN. One thing on your side though, is that if he is a loner, he probably doesn’t have a busy schedule, and thus he will be available to do things with you.
As others have suggested, you could try talking to him about deep topics. This often leads to deeper friendship, and more. That’s the way I prefer to enter relationships. Asking him how he feels about you point blank may be risky, but you can do it if you’re bold and prepared for an honest answer. Maybe he is like me, and can’t stand superficial conversations and friendship, such as most of both of these things are. You could also try to be romantic, but in a low key, subtle way (nuance will be important here).
Then order a pizza, put on an Al Green CD (I recommend I’m Still In Love With You ), and as Magickly Delicious put it, just kiss him and see what happens.
Shayna - ditto on many men not being big social planners. My best friend is notoriously vague when it comes to this.
“Hey! When are you free for <fill in the blanks> we talked about the other day?”
“Mmm … any time*-lah*. It’s up to you.” (NB: the lah suffix is a definite indicator of Malaysian-ness! ;))
“OK, how 'bout <date>?”
“Oh - I might have a dental appointment on that day…”
“Okaaaay … let’s see … <alternative date>?”
"Umm … I think I have choir practice. But I’m not sure. scratches head I need to check… err … "
At which point I tell him to pick the date instead
But of course I’m really used to this and the accompanying sheepishly apologetic look from said best friend after all these years
Back to the guy in question. I haven’t known him long enough to be able to tell whether he’s really the non-nurturing/caring type, or whether my personality can really match his, etc. Will just take things as they come along and be his friend first and foremost.
You see white, he sees black, don’t expend any energy toward finding the gray area - you’ll just be wasting time.
Rule #1: People don’t change. Period.
Never, ever go into any type of relationship (friendly, casual acqaintances or other) expecting a person to change. It doesn’t happen. Don’t even entertain the fact that your actions can somehow change a person - that’s both pompous and unrealistic.
Rule #2: If there are mere concerns in the present - in time they’ll drive you completely nuts.
Think of another person’s personality quirks that you find either annoying, incomprehensable or bothersome as cute little freckles. As time passes, the odds fairly high those small blemishes will eventually become full-blown melanoma.
You cannot make anyone do anything that they don’t want to do, nor can most people make drastic changes in their nature without a tremendous amount of effort (more effort than most people are willing to make).
As yourself: “Do I want to have a relationship with him as he is, right now?” Because odds are, he isn’t going to change. If the answer is yes, then have the relationship. If, however, you’re thinking “No, but if he did this…” then you’re setting yourself up for a ton of time and emotional energy wasted.
