Have you dealt with it though? I say this all the time to my therapist---"I should be fine, I should be over this by now!" Blah blah blah. He seems to think it's kind of cute/funny, because I'm 25 and he has clients in their 50s/60s going through the same kind of thing.

Nobody is "supposed" to mess up in life. And the way you are is definitely a product of experience. Nobody is born broken. You get that way through experience. Hopelessness is normal reaction to bad things happening repeatedly, but you don't have to feel that way forever. You aren't destined to be like your mom.