Having seen ds1 around his friends more often than normal due to the summer holidays, I am worried about the way he behaves around them. From whereever I am in the park I can hear him bellowing, "I'VE GOT THAT/DONE THAT/MINE'S BIGGER/MY BIKE DOESN'T HAVE STABILISERS - THEY'RE FOR LITTLE BOYS.." etc etc Tbh, it makes me cringe and then I find myself helicoptering, muttering to him about being nice to his friends - very ineffectual. We met up with friends in a park yesterday and as we were getting into our respective cars he shouted across to his friend's father, "X, I read in bed now!!" This is something he has started doing this holiday and I didn't know whether to laugh or cry when he yelled his acheivement across the carpark 
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A related issue is that he still has tantrums if he loses a game - these we mainly play as a family and avoid on playdates as he such a bad loser. We have always tried to balance letting him win with ensuring he experiences losing since he started playing this type of game, but he still has a meltdown nearly each time he loses.
His last parents' evening was positive and his teacher praised his social skills and commented that he has the resources to cope with frustration lacking in many of his peers. She also said children like playing with him because he is so much calmer than many of the others - all encouraging stuff but doesn't marry up with my experience of him.
We have always loosely followed the HTTSYKWL and Unconditional Parenting type of approach and tried to avoid 'over-praising' but he is our PFB and I'm starting to think we have created a monster...