One thing I’m going to try soon with my awkward and lonely ADHD 12 yr old soon is group gaming. In our small city, there’s a few different gaming stores/places where people gather to play Magic the Gathering, Pokemon, Dungeons and Dragons, etc. One of the owners recently said there’s a group where some middle school boys regularly attend. When I was homeschooling, our group took a few of the kids to a game night of Magic the Gathering that was mostly adults — a couple dozen very awkward, nerdy/dorky adults … who were just wonderfully fantastic with the few homeschool kids who attended! They were warm and friendly guys who clearly knew what it’s like to be an outsider. Unfortunately, the homeschool organizer moved away, and so we never went back. (My son wouldn’t be bold enough to go to a group of just adults and play a game.) But now that I know there’s a group that includes middle school boys as regulars, my husband’s going to take our son whenever he gets an evening off.
Maybe there’s something like this near you, and you could call and see if any of the groups have HS aged boys who regularly attend? Experts say the best way to make friends, especially for men and boys, is around common interests. It’s so hard, though, for young men and boys who aren’t athletic. I’m also going to insist our son join the robotics club at school next year, so he can meet some other boys who like that kind of thing. Maybe you could talk your son into also trying some sort of after school club, like chess or robotics? With Youtube tutorials nowadays, one can get acquainted with almost anything (games, robotics, etc.) enough to feel comfortable approaching a new thing in real life.
No easy answers, but thought I’d throw what I’m trying with my son out there in case it helps you and yours. 🙂