So, I am in love with an adorable aspie boy. We met in college when he was a freshman and I was doing a master's, he is 3 years younger than me. I spotted him in the canteen, found a clever and strategic way to talk to him, I added him on facebook... Things weren't going anywhere for months and I was sure he didn't like me, until he one day posted on facebook that he has a spare ticket for a show and I was in a courageous mood and wrote to him that I would like to go. It turned out really well, it was a wonderful evening. His younger brother and another very geeky male friend of his was there too, which seemed to give him a bit of courage. On our way home, we walked through a lovely park and the two other guys were walking way behind us, so we got some time on our own. It felt really romantic, he was so charming, and flirty, and kind, and... I felt that we managed to break the ice. I was ecstatic.
However, the next time I saw him he behaved very awkward with me. I see him sometimes, I even tried to arrange a similar 'date' once, bringing along a male friend we had in common, and it was going quite well, but unfortunately this friend had to leave early, and as a result, he was noticeably uncomfortable and shy for the rest of the day.
Also, he has this thing that when we make plans, he tends to be very late and/or show up at the wrong place/try to reach me by unsuitable methods, is this some kind of self-sabotage or shyness? Otherwise I know him to be a very organised, punctual and considerate person.
When he notices me at a public place, e.g. in a shop, at church etc., he tends to turn to face exactly the other way, pretending to read some crappy noticeboard with great interest for 20+ minutes, or study the ingredient list of a chocolate bar in the shop for an abnormally long time, or fiddle with his phone and make phone calls... You get the picture. If I do find a natural way to initiate a conversation with me, he seems really nervous at first, but eventually warms up.
Once I invited him to go to the cinema with me. He didn't even respond. It happened before that he didn't respond to facebook messages, mostly ones in which I tried to make small talk (I didn't realise that he has Asperger's at that point). Again, this is really unlike him. I once manipulated him a bit and wrote to him something like 'I am so sorry, did I insult or hurt you...?' and after some time he wrote me a whole long e-mail of pleasant small talk in response to that, he seems to have put a lot of thought into it. I was quite impressed.
Once when I already suspected that he has Asperger's, I casually brought it up in a context where it felt natural, told him that I went to school with many aspies because I was specialising in mathematics and that I do not consider it a 'syndrome', but just a personality type, and I'm not judgmental about it etc. That seemed to have made him uncomfortable, maybe because he figured that I've figured that he is an aspie...
I don't see him very often unfortunately, although I would love to, but my previous advances seemed to have scared him away mostly. I rarely talk to him in person, but when I do, he seems to be super nervous, sometimes he even stutters, although he's otherwise an excellent public speaker. He watches my breasts a lot. He seems to realise this and he seems to feel guilty about this. He also seems to be trying to make a good impression on me.
I think the flirtiest thing he's ever done to me was on our first 'date'. His brother was there as well which made him feel more courageous, it was already quite late, we had already spent a relatively long time together, so he was relatively at ease. We were in a pizza shop and he sat on one of those tall bar chairs, and started balancing on it while making a funny face, winking and making eye contact with me. Then he jumped off the chair, walked up to me, and started watching my breasts really intensely.
I haven't spoken to him in person since last summer unfortunately. I used to go to the church where he goes fairly often, but last autumn I put an end to that, I wanted to see what happens. As a result, he started contacting me on facebook quite often, posting clever, funny and/or cute things on my wall, and sometimes even being a bit flirty.
That's where we are up to now. I really don't want to scare him away. What would you suggest that I do? As you may have guessed from the above, he's really shy. How should I make him feel more comfortable around me? Is this some kind of phobia? I always try to come off as really laid back, friendly and non-judgmental with him, sometimes I even make self-deprecating comments or pretend to be nervous too just to make him feel more at ease, which seems to work to some extent, but not enough - as you can see from the above. Any good ideas, or comments? :s