I was a less active female version of your son. I was bullied from the moment I started school till I got so fed up I had to drop out in 9th grade. I was severely shy, got bad grades because I was depressed so I was called stupid, I was obese once puberty hit (emotional eating) so I got called fat and ugly a lot and called names like Shamoo and free willy. I stayed home from school as much as possible and every grade the teaches wanted to hold me back despite the fact I was smarter than most of my peers (in middle school they even tried to put me in special ED). I even sometimes got beaten up. And not only did my peers treat me this way, many of my teaches treated me like crap as well. Being called a failure in front of your entire reading class is a really great way to make an already depressed kid want to go off the deep end. Then I'd go home to a mom who was depressed herself and had no idea how to cope with me. I was diagnosed with post traumatic stress disorder and put on SSI a few years after I dropped out. I had nightmares for years.
The unfortunate thing about being a kid with these problems is that you aren't equipt with the ability to articulate what you are feeling, what's going on in your head. This is probably why therapy isn't doing a whole lot of good. I'm sure he's depressed and anxious and feels like he doesn't have a voice. And if the therapist has never experienced childhood trauma herself, she only knows what she's read and been taught about it. Unless you've lived it, there's no way of knowing for sure. Also keep in mind that not all therapists are created equal. Mine were terrible and had no idea and didn't help a lick. Maybe you can try to get him to take up journaling? It's helped me a lot from an early age. If he's having problems articulating, maybe he could take the journal to his therapist so she could get better insight?
You also may want to try getting him involved in something that's less socially stressful, something more low key that doesn't involve a large group of jockish pubescent boys (they are the worst!). It's way harder for a kid with social probs to make friends in large groups. I still freeze up in large social situations... it's like stimulation overload. I've always made friends in small, intimate groups. He's probably very introverted, introverted people express themselves much more freely where there's less pressure to be extroverted.
I had the hardest time making friends, like your son, but despite all I went through I managed to make a few. I didn't make a real friend till I was 14... 12 years later she's still my best friend. For a long time she was the only friend I had other than pen pals (thats also a good suggestion... some of mine I still keep in contact with and have even met in person in recent years!). Even after moving to NYC It's taken me a few years to make close friends. But I did it! It's just really hard for some of us. Luckily your son has an edge over most kids who go through this. He has an understanding mom that's doing her best to help him. And the fact that he tries and is active is really something. That shows some strength right there. I really hope the best for him!
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