My boyfriend is an exceptionally bright, hardworking man that always gives 100% in friendships, work, and volunteer activities. His last girlfriend was immature and constantly put him down for “not understanding her”. She never clearly communicated what she needed from him or the relationship and instead decided to berate him any time he did something she didn’t appreciate.

For example, towards the end of their relationship he decided to go on a vacation with his several of his close friends to visit their mutual friend, L 27F, in the Virgin Islands. They decided to go on this trip because she’d become depressed and lonely as a result of moving there for school. L has never been in a relationship and was often the odd woman out at every friend event. As a result, the friend group decided it would be best for just the core group of friends to go on the vacation and leave their SOs behind. A week before the vacation, they all learned that one friend, C 27M, had bought a plane ticket for his girlfriend to come because he’d “missed the memo” about not bringing partners. They all decided it would be unfair to force C to forfeit the tickets and allowed her to accompany them. This enraged my boyfriends ex. She claimed that they had all plotted against her and that it was unfair that one girlfriend got to go while she didn’t. She screamed and pouted for the entire week leading up to the vacation that my boyfriend wouldn’t force C to tell his girlfriend to stay home. The vacation happened without a hitch and, as a consolation, Brendan bought her as many gifts as he could fit in his luggage. When he arrived home with them, she pitched a fit that one of the gifts was a ceramic shark head. She screamed about how much she hated it and that she couldn’t believe he thought she would like something like that.

Things like this continued, with him trying his best to get her to communicate, and trying to better himself until she finally ended the relationship. He has developed an OCD fixation, diagnosed, on this past relationship and at least weekly laments about whether or not he did everything he could to try and make her happy. He is now convinced that he is terrible at reading people, inconsiderate, and is incapable of making people happy despite being the kindest, most considerate person I know. He has tons of friends and family that love him and tell him the same thing. To this day, he refuses to admit that she had any fault in the relationship, that she was too immature (21 while he was 25) to nurture a healthy relationship, or even that they just weren’t right for each other. He reacts to me treating him with basic kindness as if I’m a saint to the point of it making me feel incredibly uncomfortable. He forgot about us planning a date night and when I reminded him the afternoon of he completely deflated and apologized profusely. All I said was, “It’s ok baby, I know it’s been a full and stressful week, but maybe we can go forget about this on our date? My treat!” He looked at me, tearing up, and said “you’re not mad?” “Of course not, baby! Everyone forgets stuff every once in a while.” He cried in my lap for about five minutes saying that he couldn’t believe how patient and kind I am.

He has shame-oriented OCD that frequently surfaces when something goes wrong or when he is stressed. I have worked and worked with him and now he is comfortable sharing most of these thoughts with me and I do my best to rationalize his delusions about himself and affirm that he is a good person who just messes up sometimes, as we all do. I am the only person in his life that he feels comfortable enough to confide these feelings to. He hates the thought of anyone else knowing about his “shameful” past.

However, I just don’t know what to do anymore. He doesn’t think he’s good enough for me and every time I bring up any small criticism or concern about the relationship, he takes it as a sign that “he was right” and that he doesn’t deserve me. Every problem now ends in him saying he’s not good enough, stupid, inconsiderate, or too mentally ill. And then he apologizes about complaining about these things or sharing them with me.

And it makes me so mad! I can’t help but be frustrated! Why can’t he see what I see? I feel like I’ve been pushing on a brick wall for a year. I’m exhausted. I even resent him sometimes because it feels like his problems take precedence over mine. (Even though I’m the one who controls what we prioritize. He absolutely drops everything and comforts me when I need it.) I just don’t react as strongly as he does. I can safely put away my feelings on a subject to deal with at a later date.

I’ve done everything I can to help. I’ve read every article. I’ve asked if he would speak to others the way he speaks to himself. I provide constant evidence against his claims. I’ve grounded him in reality. I try to focus on the good parts of life while allowing him a space to voice his concerns. I’ve even tried telling him that I don’t tolerate ANYONE speaking so negatively about the people I love, even themselves. I’ve tried to encourage him to thank me for helping, instead of constantly apologizing, which he then apologizes about.

I don’t know if me entertaining these thoughts just feeds the OCD? I honestly have no idea what to do. What do I say? How can I help? My own mental health is suffering and I’m running out of spoons.

Thanks for reading if you got this far, honestly I feel better just venting a bit. I appreciate any and all help in advance 😊

TLDR: A previous relationship has made my boyfriend feel permanently inadequate and I don’t know how to respond to the constant self-hatred anymore.