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Dear dreaming715:
You wrote: “it feels borderline confrontational (like I’ll try to word it nicely, but he’ll become confused, feel like I’m nit-picking at him”- it seems to me like you really are confrontational and nit picking.
Example # 1: I don’t think he was thinking something like: “dreaming715 can’t tell the weather. She is unreliable, inadequate and maybe she is lying, I better check the weather myself.
I think he was thinking something like: what? How can it be raining there? It is so clear here!” And then, out of sheer habit, he did what he usually does when he is confused about the weather: he checked the weather on his phone app.
Example # 2: When you asked him about people of low/ moderate income investing, he was speechless for a while, I believe not because he was thinking something like: “dreaming715 is clueless. How can she be so ignorant?” I think he was clueless for a moment himself. Simply didn’t have the answer for you right there and then. He soon found the answer by asking you about your 401K- there, he came up with the answer he didn’t have a moment ago.
Seems to me you are personalizing, that is misinterpreting his behavior to mean what it does not. You assume he is communicating to you that you are confused and clueless while in reality, he was confused (example 1) and clueless (example 2).
And because you misinterpret his/ others’ behavior to mean that you are lacking, you are bound to be confrontational at one point.
Better ask him what he meant by what he says, just so to get the correct meaning in what he says, to check against your assumptions.
anita