Dear Ryan,

I think my issue is more that I feel a sense of guilt/shame when I hurt or disappoint women. It feels as though women see me as something that I may not always be: A good man or a better man than most. I try to live up to their expectancies but often don’t.

Right, so this would be a problem of feeling not good enough, even though e.g. your ex was singing your praises how good and amazing man you are.

But if we don’t feel good enough – if we feel there’s something inherently wrong with us – no amount of outside praise and convincing will do. Sooner or later we’ll do something to “mess up”, and it will be a proof to ourselves and our partner that we indeed aren’t good enough. Self-fulfilling prophecy….

Earlier we talked about your lack of self-worth, and this is similar, feeling not good enough, perhaps feeling unlovable? It all has to do with your childhood. Did your mother frequently criticize you? I know she scolded you for not using proper language, but did she criticize you a lot? How about praise – did she ever praise you? How about your father?

If you’d like, describe a little bit your relationship with your parents, specially your mother, because I believe that’s the key to understanding your current problems.