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Sorry for the self-divulging ramble.
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Thank you for explaining in such detail.
Here is a guess. I am thinking that your mother's control is a main root of the social problems. What you learned growing up is that there was no point in being active or taking initiative because your mother was going to intervene and control. Maybe she was like my mother and screamed at you if you dared to disagree. But even if she was not a screamer, she took so much control that you basically figured, perhaps subconsciously, why bother expressing my own ideas? And you became passive.
Also, changing schools so much was socially harmful to you, in my opinion. You perhaps saw no reason to connect with people because you would likely be leaving. And people do in fact learn social skills by being with the same or similar group over time. There is more to socializing than meeting someone new.
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Actually, my mom remained pretty uninvolved in my social life
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She didn't have to be directly involved to affect it. Family relationships affect the kind of person we are, the ways we express ourselves, and those background factors affect how we act socially, as well as how we act in other areas of life.
If you can control the choice of T, my suggestion is to avoid the Ts who give assignments and possibly "fire" you and want to improve time management. Problems in those areas are symptoms, not roots. Such a T would be doing again to you what has already happened to you in your life.
I think you have the right idea of issues to focus on, but I would add that a T should hear about your childhood relationship with your mother as well. I think you would do well with a T who has a psychodynamic orientation. The T should not take a lot of initiative in speaking but should help, encourage, and wait on you to speak.
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But yeah, we could have 3 or 4 appointments and I'll barely get to talk about what really troubles me.
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This is because the relationship with T in session mirrors relationships in real life. You are passive in real life and so you are passive in session. In real life you don't speak about what is actually on your mind, and you don't do that with T either. A good T, though, should realize this and, over time, allow the relationship and trust with her/him to deepen to the point that you
can say what is truly on your mind. It will be a great day when that self-disclosure begins to happen.