How to break the cycle of insecurity and reassurance

Last week he told me he's thinking about dating a woman he connected with on OKC, they knew each other years ago and always had a crush on each other. He wanted to ask me how I felt about it? I got the feeling he was being really considerate. That I am important to him and that he does not want to hurt me. BUT. It was like I was thrown into a time warp. Am I really going to go down this road again? Guy meets other girl, she's single, he has mono tendencies, wants her to be his primary? Is it my stupidity that has landed me in the same situation? Or is the situation actually not the same at all and am I just triggered by similarities?

Hmm, it sounds like you are reacting to the memory of how things went with C, rather than the reality of this development with Brig. However, Brig hasn't only said he's "thinking about" dating her? And you don't know if she's mono-minded or not. In addition, his wanting to know what the "rules" are sounds like he wants to be considerate of you first before anything.

I would say, don't be afraid to talk about this with him. It doesn't necessarily mean you're asking for reassurance to want to know what he envisions for himself and for you. You can tell him about how C's other relationship affected you and say you hope nothing comes between you and Brig because you enjoy it so much.

And then trust.
 
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