I'm strongly weighing the pros and cons of my relationship (a couple of years, living together, no DC, both soon 30). I feel stuck whatever path I choose. Basically my boyfriend is pretty insecure and it's weighing me down. He can be so loving, caring, helpful, funny, entertaining, you name it. But it all is accompanied with his insecurities. These manifest themselves in passive-aggressive behaviour, no substantial relationship with his family, envying his "rich and successful" brothers, criticiseing the whole world all the time and lashing out when things do not go the way he wanted/planned (no physical violence). He can be cheerful and happy most of the time, though, but these behaviours are still present all the time.
We have talked about these, but I have trouble helping him. I do not know how to help. I have tried listening and explaining how his thoughts are essentially wrong (thing I learned from my therapy when I dealt with insecurities many years ago). I have encouraged him. I have ignored him. He also went to counselling some time ago, claiming he really really wants to change, used only a small amount of sessions as part of his insurance plan. He said it helped. He put notes and reminders about what he learned to visible places and he showed some signs of improvement, but now most of it has vanished and he has removed the notes as well.
One path would be to try to help him more, be more giving and loving, but I find it difficult to do. Firstly, I really do not know how to help, and secondly I find it difficult to be loving, if he criticises the world, is negative etc. I truly loved him at one point and gave a lot of love and all, but his insecurities somewhat killed the love.
Second path would be to break up, but the same insecurities keep me from doing it. I Would feel so sorry for him for causing him so much pain, to leave him all alone in the world and be the next one in a row to break his heart as his previous girlfriends have done (as he has told me). He has not said much about the previous girls, basically he says he instantly forgets everything about the relationship after break up. So I have not heard anything good or neutral. But I have heard from him that the girls were bad and ditched him or cheated on him. Part of my brain thinks he is just manipulating and he will be alright, he will find another girl and life goes on. But half of my brain thinks I will mentally kill him if I break up.