My DD has ADHD and although she doesn't know this label she is highly aware of her challenges. We talk a lot about our strengths and weaknesses; I share mine too and I think it helps put things in perspective. It is especially interesting to hear my kids tell me my weaknesses ?

I would make him some social story books so that they are personalized to him and his friends on "what to do on a playdate" type of things. Make sure too that when he does say things like "my brain is not good" and "I'm not smart" that you tell him positive things like "your brain is really good at things like math and ___" and "Yes you are smart - you're so smart you know all those math facts" or things like that. Let him know that everyone is different and it's OK that he's good in some things but not others because that's how we all are. Continue to give him social situations and skills as he can handle it - it sounds like you're doing great so far!

Model behavior with him. Narrate what you are thinking or feeling when you are with him. Don't be afraid to tell him negative things, like if he talks about numbers, say "I am bored," but don't say, "you are boring" or "that's boring." Roleplay with him. Pretend to be another kid and roleplay a successful greeting or playing a game together. Have him roleplay another child as well (he may have trouble with this, but try anyway).

If he does have ASD eventually, you will want to put him in social skills classes or Unstuck and on Target (has to be age 7).

Get the book "Social Stories" by Carol Gray and learn to write Social Stories for him.

http://carolgraysocialstories.com/social-stories/

Ugh, op, telling a young child to think socially is ridiculous.

He IS thinking socially for him. Get the rick Lavoie book it's so much work to be your friend, and look index on how to host a play date.
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I would also focus on a growth mindset rather than a fixed mindset (if you google those terms you'll find lots about how to inculcate growth mindsets). Nobody's brain is good or bad. Nobody starts off good at everything. Everyone is learning. Everyone can improve. He can improve at making conversation and playing with kids.

I think that some of the messages that your child has internalized come from his already knowing that his brain is different... and unfortunately, the message from the NT world is that different equals not smart and no good.

I have a child with ASD and try to balance in times where he can be successful being himself. If that means letting him have time to talk about numbers (which mine does), then I find activities that he likes. He likes math games and keeping score during sports on TV! LOL!

If unstructured playdates don't work, we don't do them -- or we don't do them with certain kids. He has plenty of time with the NT world... home and playdates need to build him up (as much as possible).

I'm not saying that your kid has ASD. But he knows that his brain is different and you should validate that feeling... while letting him know that different is just as good.

I absolutely think you should scaffold playdates.

When my son (adhd, anxiety, also introvert) was that age, I tried everything until I found formulas that worked. For him it would be one kid at a time and some planned activity that was super appealing to my son (since most friends would do pretty much anything). I had to be ready to jump in energetically and play at times and I had to be ready to let son escape and be by himself for a bit for a break. I was actually very grateful for siblings because I felt like the ensured that friend was having fun the whole time and would return. We hosted constant play dates... at that age kids are not very critical (or necessarily very perceptive) and my goal was to keep kids coming until my son got comfortable with the individual kids--which I knew would take a long time.

I know it's incredibly hard but you have to view this as a very long term project. Sometimes my son would participate in half the play date and then need alone time to recharge. It was completely counterproductive for me to tell him he was being a "bad host" ... I had to built up his skills (and his tolerance) little by little. I had to take it as a victory if the next time he participated in two-thirds. Also my goal was to foster some real friendships not just work on social skills.

I am not saying that my son is class president now as a middle schooler but the slow steady approach totally worked. He has several very close friends. he is still an introvert but he definitely has picked up social skills.

It sounds like you are doing well. Facilitating or scaffolding is still necessary, I think. And working on pragmatic speech with an SLP -- turn taking, staying on topic, can help.

You might help him plan for the playdate before, not just give feedback after. Could you also 'practice' social skills when he interacts with his siblings?

DS, who hasn't yet been diagnosed as autistic but is in line for a neuropsych scheduled for early next year, has really been fixated with numbers lately. He's not by any measure a genius with numbers and tends to exaggerate with them - he'll whine that a haircut will take "75 hours" and that cleaning up toys will take "600 minutes." He frequently brings up math facts in conversation...which of course doesn't make for much conversation. He had a playdate today and did just that. He told the girl that "600 is 100 more than 500," and of course his friend didn't make much of that statement and proceeded to play more with DS' siblings. He frequently says things to friends that are out of the blue and seemingly irrelevant, so I've noticed friends not responding to DS and playing more with DS' siblings.

After the play date, I encouraged him to "think socially" and think about the friend he's playing with as he comes up with things to say. I told him that five year olds don't want to hear math statements per se, but want to do joint activities, like color together, run around, play games, etc. I told him that just because he's thinking about a math fact doesn't mean that his friend wants to hear it - so I was encouraging him to think about what his friend likes to do. Of course, perspective taking for kids with ASD is very hard. After hearing all this he said very simply "my brain is not good" and something to the effect of "I'm not smart." It broke my heart hearing him say that. This was the second time he's revealed that he's aware that he has deficiencies in the way he thinks and behaves.

My questions are, what can I do to help him improve his social skills? Should I continue to scaffold his play dates and try to coach his behavior? Has anyone had luck using social skills modeling videos to really drill in basic social thinking? Also, should I start talking to him about how his brain is wired differently, which makes things like playing with other kids a little more challenging? The fact that he seemed more self-aware now really got to me.

He is not in a formal therapy program at this time. We are in the process of finding him a speech therapist. He did play therapy recently and after about four sessions, the therapist concluded that he's not autistic. He's currently doing well in K and is able to handle the schedule, activities, and being around 24 other kids without accommodations yet. He's also part of a social skills lunch program at school. Other than being shy and introverted, he did well in pre-k and made some friends, but he still has a hard time connecting with friends. I just fear that he will not be able to make lasting friendships and am afraid of how that will impact his life.