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You really should get into therapy about this and just try to get to the bottom of it. Chances are it goes even further back than one girlfriend cheater. Psychiatric care is privileged, best I can tell, unless the patient signs a release. I only know this from having had jobs getting legal medical records in the past. When I tried to get them with a subpoena, they still didn't turn them over. And some won't even talk to you even if you have a patient release.
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The thing is, I read that one of the best way to do that is with the support of your partner. Having an understanding partner that can give reassurance when required and tolerate the little bumps on the way to becoming more secure seems to be key from what I read. But that entails opening myself up a lot and showing a vulnerable side of me that obviously isn't super attractive.
gamer huh? He should like zombie movies! I say if he asked you out the first two times, and considering he mentioned you two were out on a date and you were too shy to say something, I think he might be getting mixed signals from you. He's not sure if you are interested or not. I would ask him out to the movie and see what happens from there. It has to be a give and take, and since he's asked you twice now, it's your turn to ask him
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