Asperger Syndrome Support Group
Asperger syndrome - also referred to as Asperger's syndrome, Asperger's, Aspergers or just AS - is one of five neurobiological pervasive developmental disorders (PDD), and is characterized by deficiencies in social and communication skills, normal to above normal intelligence, and standard language development.
Things that I did include:
Saying a phrase with different tones. He was focused on Thomas the Tank Engine at the time, and I remember saying "I like Thomas" in a nice way, mean way, etc, etc. And asking him how it sounded to him. I did that every day for about 4-6 weeks. Then probably every 2-3 days for weeks afterwards.
Stanley Greenspan's floortime approach helped a lot too.
http://www.stanleygreenspan.com/
I never went to any conferences or paid for anything. I just read about it online.
The basic idea is to spend 15 minutes with your kid everyday (or multiple times a day) just following their lead.
At the time, my son would line up his matchbox cars for hours. At first he hated it when I moved a car. As the months went by, he became okay with me moving a car and taking turns. Two or three "circles" of interaction were a victory. Four or five were a miracle.
I can't say that he ever "pretended" though.
"Social Stories" have been useful for some kids.
https://www.google.com/search?q=Social+Stories&rlz=1C1CHWA_enUS626US626&espv=2&biw=1600&bih=799&tbm=isch&tbo=u&source=univ&sa=X&ved=0CCwQsARqFQoTCKW-9PuU4MgCFcMYPgodMD8PUg
I never did them. I don't remember why. Maybe I was just too exhausted at that point.
I also have a daughter (two years younger), who's got more social skills than anyone I know. I learned a lot about how social skills work by watching her. And she worked HARD at pulling her brother along.
What is he interested in? Maybe plugging him into a program that serves his special interest with other kids could be a starting point. Ryan did not make friends easily in high school, but when he went off on his own to play on cruise ships and was left to his own devices, he acquired social skills real quick because was so lonely. He pretty much forced himself into social situations, and when he came back, he had a confidence I had never seen before! Again, I think the best is to practice with him a little each day and see if you can help him get involved in a team or group that share similar interests. It'll be that much easier because finding conversation and things to talk about won't be such a hassle.
on the other hand, I call my mother my translator, and I think what you are doing for your son is wonderful. It requires patience. Sometimes I joke with her that our conversations are like that "Who's on first" Abbott and Costello joke, lol...
When I interact with people and she is with me, we talk about it afterwards. she talks about my responses to them and how I interacted with them, what I said, how I looked, how I sounded.
It has been a long slow process, but in the year plus since I was diagnosed, she and I both agree that I've come a long way.
I just wanted to say what you are doing is awesome and will help him in the long run. Just remember, we tend to need detailed, logical explanations to understand. And if he is willing to try, then that is a good thing, even if sometimes you feel frustrated.
I'd try to facilitate his involvement with any kind of club or interest group, help him get there, help him stay involved. He'll learn by skinning his (metaphorical) knee a few times. Maybe some group with mainly older people - stamp club? Church social group?