Dear Umm:

From my experience and my understanding, your boyfriend is emotionally wounded and is in pain. Every time he asks you questions about your exes, he is trying (although ineffectively) to free himself from his pain. It is as if, in his mind, the “correct” answer by you, will free him from his pain.

Asking you questions about your past, may have become his habit, maybe an obsession. If I am correct, then what happens is that every so often, triggered by this or that (be it a name of a restaurant or your use of a particular word in the story about the friend who mistreated you), he feels something like a mental itch that he .. just has to scratch, so to speak, by asking you yet another question. You answer him, he finds a relief from the itch, at best, but it is only a matter of time before he feels the itch again, and he just has to ask you another question (or spy on your/ your exes’ social media accounts).

Again, if I am correct, then he feels that there is something wrong with his behavior and he tries to not ask you question, spending a lot of time troubled but keeping silent.. until he gets especially triggered, the itch is too strong and he rushes to scratch it by either asking you yet another question and/ or spying on social media accounts.

This might have been his behavior with his ex-girlfriend as well, spying on her social media account, and that’s why she blocked him (“his ex blocked him”).

You wrote earlier: “I wonder if he still loves his ex.. now I end up feeling I am a back-up person in this relationship.. like I’m in the middle of their unresolved case”-

– if what I suggested so far is true enough, then his pain, his emotional wound was not formed as a result of his previous relationship, but way back in his childhood. His pain is not an indication that he loved his ex-girlfriend more than he loved you. It is an indication that when he feels emotionally attached to a woman, the injury opens up, and he feels the pain.

Does this make sense to you, and do you  know anything about his childhood?

anita