He's had the same friends since primary. But they have been on and off over the years. It is very rare he spends time with them out of school too and if so it is only for an hour at a time.
I find asking any questions later after tea rather than straight after school I get more information out of him regarding school, seems to work okay for us. The school emails parents when children receive merits and demerits. I asked one day what he got a merit for and his answer was "doing nothing"
so I contacted the school. All the kids in his class were mucking about and carrying on except him so he gained a merit for being respectful. Technically he wasn't lying when he said he got it for "doing nothing".
It can be so hard for them to maintain friendships and I know for us parents it can be such a worry and quite sad thinking they have no friends. But if they are happy in their own little worlds that's all that matters. He speaks to kids in his class so maybe that is enough for him socially. As I've gotten older I've realised I'm not really a people person. The whole masking and being sociable and putting on a front is actually quite tiring and draining. I find it easier to type to people than actually talk. Unfortunately with my work I do have to talk on the phone and after a shift I'm mentally drained sometimes. My daughter is the exact same very bossy and games have to be played her way. I'm sure over time it will get easier. Just keep trying and with consistency hopefully his social skills do improve and if they don't but he is happy that's all that matters
we're not failing our kids and their needs so long as we keep trying for them.