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What makes a woman high maintenance and difficult read these 15 signs of a high maintenance woman to know if you're too rich for your man to afford. I was recently told that for a small town girl, i certainly seemed to be high maintenance i didn't take the time to ask what that was suppose to mean, but i'm. Dating high maintenance woman - if you are a middle-aged man looking to have a good time dating man half your age, this advertisement is for you register and search.