Realistically, it really is all up to him now, isn't it?
Briefly: He's a bit reticent, and will never be the centre of a social crowd. He moved into Y6 of a primary that 'feeds' our secondary of 'choice' (bearing in mind a) we weren't at all happy with the Y5 catchmented secondary and b) he would not have been in any of the same sets as his 'mates' from Y5). He sort of made a few friends at the primary, but we knew he, with his personality, would have been unable to 'break into' any 6 year old friendship groups.
Anyway, secondary (he's now in Y8) has ostensibly been 'fine'. He's doing OK academically BUT I'm not sure he has any proper 'friends'. Weekends are getting a bit tricky as DS2 (Y6) heads out with his mates (and with the advantage of joining the feeder at the start of Y4 AND the ability, in primary, of mum being able to facilitate some friendships!) but DS1 has a mate who he might meet up with but it always seems to be entirely at this other boy's convenience and if he hasn't had a better offer. And DS never invites this boy into our house. I am aware that the other boys in his tutor group go to the cinema together, or trick or treating but DS1 never gets asked along. I'm not sure how he even knows about such events, tbh.
I try ever so gently to talk to him about how to 'nail' friendships but I am also very aware of the risks of him suddenly thinking 'I'm Billy No Mates! Mum thinks so, too!'. I think he lacks the confidence to 'join in' with the chat like, presumably 'Hey, what time will we meet/where tonight for Halloween?' and for him to say 'OK, I'd be in on that, see you there' . The instigator of the ToT is local but arrived in the area after primary so he's not pulling on Primary mates, but he is, apparently 'popular' and DID invite DS1 to his paint ball party last year but a few initial Y7 calls of 'Mum can this boy come home with me for an hour tonight?' from the homeward bus have dried up. Presumably he doesn't find DS1 engaging enough!
FWIW I passed him at the (late) school bus stop yesterday morning. There was a clump of maybe 20-25 kids there, including 2 from DS's tutor, I happen to know. I thought 'I'll never see DS in that lot!' but I did- standing 3 paces away from all the rest, alone! He says 'They are all boring idiots who only talk about violent computer games and football so I sit by myself on the bus'.
DS does Scouts with an altogether different bunch of boys, some of whom he's been in scouting with since he was 6 but they also never seem to lead to proper 'friendships'
Now, on the face of it, DS1 doesn't seem that bothered but I sense he is. I know he's desperate to appear 'cool' so would never confess to me that he feels a bit friendless. But I worry that gradually, as is already happening, DS1 will find himself alone of a weekend, knocking around the house with us when DS2 is out and about. Currently, DS1 might hang out a bit with DS2 and his mates but he is aware it's a bit uncool, being 12 and hanging with 10 year olds- even though many are taller than him! I tell DS1 to get the mobile numbers of a few more boys in his class for long holidays etc but he never seems to 'get around to it'. I suspect he's scared of ridicule or rejection, tbh.
FWIW, DH is a loner. He doesn't have many friends (and seems 'OK' about it) but he has formed some friendships over drinking real ale and beer festivals so I am thinking DS1 probably takes after him but I still wondered if there was anything I might do like IS there any point in talking to the school? We have very little contact with school- I have never eyeballed his Tutor, for instance! But really, is Y8 too late for me to do anything apart from trying to pitch 'encouragement' at the right level?
WWYD?