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Dear Lea:
From your recent post I understand that he negatively judged you for being of a higher social status and therefore you didn’t have to work in order to get the material things you received, somehow expressing to you that you are “an abomination.. a bad person” for being born into material privilege (?)
You tend to agree that his family life was stressful, there was tension in the air (“Lots of stress at home”), and his interactions with his parents increased his distress, so he instinctively chose to turn inward, to withdraw from social interactions (the making of an introvert). He repeatedly withdrew from you because he is anxious and his way of lessening his anxiety to withdraw.
His mother was strict, “maybe she overprotected him actually, she is certainly very bossy and she seemed to have taken decisions for him many times regardless if he.. was ok or not with that (e.g.,.. being pushed into a business school while he never wanted to work in this area).. He talked a lot about his mother, she was his reference, more than his father”- when she forced him into making her choices, sending him the message that he is not capable to choose well for himself, when she overprotected him, she also weakened him.
Maybe he became feminine so .. to please her (not so to please his father, like I suggested earlier as a possibility). Maybe he submitted his masculinity to his mother, so to gain her acceptance of him. When she rejected his feminine appearance and behavior, that must have confused him, creating an ongoing conflict within him, because the result of his efforts to gain her acceptance resulted in the opposite: her rejection of him.
Developing this idea/ possibility: he developed to be who he is by trying to please his dominant, bossy mother, choosing a career path she chose for him.. and on an instinctive level (it was not a thoughtful choice), he chose to be the feminine child that she wanted him to be (not realizing that she wanted him feminine in the sense of submitting to her will, but she didn’t want him to appear feminine.
anita