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So far what I usually say is "Oh HB, don't be so hard on yourself, that's what I'm for! *new topic*". Any feedback on that specific line?
I don't use any specific line, but what I do is relate her problem with something or someone in my life.
Example:
HB: I'm fighting with my sister.
Me: Yeah, I use to fight with my siblings all the time, we always ended up working things out though.
HB: I have too much pressure from school and work.
ME: Yeah it can get overwhelming, but what I do is take it one step at a time.
or use someone else.
HB: I'm fighting with my sister.
Me: Yeah, my buddy fights with his sister all the time too, but I can tell they still love each other.
HB: I have too much pressure from school and work.
ME: Yeah, my cousin works 8 hour shifts and goes to work full time, I think it's too much for him, but he seems to handle it.
The idea is that you don't need to give any advice at all. She doesn't really want to you to resolve or fix anything for her, she just wants you to acknowledge, understand, and accept her. By relating her problems to things or persons in your own life, you are basically letting her know that such things don't freak you out because they already exist in your life. In this way she doesn't feel like she would be burdening you with her problems if she entered your life, and therefore would be less fearful of doing so.
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I guess I need to stop finding insecure girls ^^.
All girls are insecure about something in their life, some just deal with it better than others. I doubt if you are looking for insecure girls. They probably just find you, because you project a safe and caring attitude toward them. Also you might just be pursuing women at a slightly lower level than you deserve (in terms of a superficial sense of value), without realizing it. Women are often reluctant to date a guy who is "out of their league", they don't think they deserve it.