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I apologize in advance if this is a bit of a long read.

Background of us: I'm 27 and my boyfriend is 29. We've been together almost three months and things are going really well. We spend a lot of time together, we're open with each other, he's supportive of me and my career goals, and he's introduced me to his family. The only problem is we both have insecurity issues. Mine stem from past relationships and my own self worth. His stem from the fact that he was a big guy all his life, but in the past year has been working out and went from 320 to 220 pounds (he's 6'1''). He's the middle child and has four siblings and he was never given the attention or praise his younger brothers were. In general, he has some issues around feeling wanted, loved, and appreciated for who he is.

Background of him and his ex: He's a serial monogamist and has been in three longterm relationships in the past 8 years. The third relationship was with a girl named S and it ended last winter. He's never trash talked her but he's made it clear to me that they weren't right for each other and she didn't treat him well. She cheated on him and was emotionally manipulative but yet he still loved her. I donít know how that works but Iím not a psychologist. After they broke up, he rebounded with his second ex and then in January of this year he cheated on the second ex with S. He was upfront about this with me very early on and assured me that he never plans to do that again and hasn't forgiven himself for what he did. He feels that as bad as S was to him, he can't judge her because he cheated on the second ex with her. They still occasionally talk over email (he was upfront with me about this too). When he told me all of this, I was clearly not 100% ok with it and he offered to cut contact with her if it makes me uncomfortable but I didn't feel right asking him to.

The current situation: He always leaves his phone next to me when we're sleeping (the outlet is on my side of the bed) and he never leaves it locked. I made the mistake of going through his phone last week (I know that wasn't right) and I found that he and S talk weekly over email. It's all friendly correspondence and he did mention me to her (she's also dating someone) and it's almost always her initiating conversation. There was no discussion about meeting up and no romantic exchanges. The only reason I was bothered was the frequency of communication and the fact that seems engaged (i.e. not just two word responses). We talked about her over the weekend (I brought her up) and he was very open to hearing my thoughts. I told him I'm afraid he might repeat his past mistake with me and he was a bit on the defensive, saying he doesn't want to feel judged for his past. Then we talked about her again last night and I told him I feel very insecure about their correspondence and I need reassurance that his feelings for her are in the past. He was less on the defensive this time and very loving and gentle. He told me I'm the only person he wants to be with and that he doesn't need to talk to her. Again, I couldn't bring myself to ask him to stop talking to her so I told him he should make his own decision.

I guess my issue with this is I can't understand why he would maintain contact with an ex who treated him as badly as he said she did. I wonder if it's because she ripped him of his self esteem, and now he's trying to piece it back together. It's weird how it works but I talked to my therapist about this last night and she helped me understand. Sometimes you go back to your abuser to understand why it is they abused you and to regain some sense of control. Has anyone ever been through something similar and can offer me some advice?

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