Dear Kristine:

My new input today: you wrote regarding running into your boyfriend’s former college sweetheart of eight years: “We ran into her and her husband  one night and ended up hanging out with them in a bar after. I hated every second of it. He could tell I was uncomfortable so he was extra affectionate but instead of trying to make me feel better on the ride home, he just kept telling me what a great person she was. ‘Isnt she just one of the most genuine people you’ve ever met?’ Blah. blah. I think he thought I felt threatened by her romantically.. It makes me feel not good enough, like I won’t live up to her… It makes me feel like I’m his second (or third??) choice”-

– it is possible that this is what he wants you to feel: that you are not good enough for him, that you are not his first choice, and this is why he shared with you so much about his past relationships, about his many exes that he keeps in touch with and still sees once in a while, about how he cried after his marriage ended, and that he regrets the long relationship with his former college sweetheart ending, that he was an idiot for ending it, etc.

And this is why, while knowing you were very uncomfortable during the meeting at the bar, he “kept telling” you what a great person she was. It was not a single comment that he made about her, but he “kept telling” you,  going as far as asking you that question, about how genuine she is, rubbing it in.

If he knew how comfortable you were, and if he believed that you were jealous of her, or threatened by her, why did he choose to promote that discomfort, jealousy and threat?

It is possible that after your 20 year marriage of “many bad times”, your difficult divorce, and 7 years of dating men who “didn’t want serious relationships”, falling “hard for a small handful but nothing ended up serious”, being at that point in your late 40s, or early 50s, when you met your boyfriend of 3 years- you were very invested in seeing him in the best possible way: “He  is more than I could have hoped for. He’s kind, genuine, affectionate, caring. Good sense of humor, I could go on and on… I never question his love for me or his commitment to me”-

– maybe his low self esteem is such that he needs you to feel less-than about yourself, so that he can feel more-than about himself.

anita