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Dated a woman for over 3 years. We broke up/got back together around 7-8 times over this period. Unbelievable for me just to admit that. It is literally driving me nuts. I am in my early 40's, handsome, do well financially, and for the most part very laid back. No kids, no ex wives, just a couple broken engagements over the years and a couple long term relationships (including this last one). I have always ended past relationships and moved on nicely, even becoming friends with most. This last one has taken a toll on me, however, that is incredibly hard to shake.

 

We met by chance, her being very attractive, witty, and charming. The attraction was instant for us both. She is twice-divorced, a child with each ex husband. Both are now teens. That probably should have been my red flag at the time, but I had never dated a woman with children and decided to give it a chance. She was very sweet and made it easy in the beginning to think that there would be no issues regarding all this. Over time, I noticed that I was paying for everything that related to our dating. Even trips taken with her children. In addition, I also noticed her children had a sense of entitlement to the finer things in life, just like their mother. She makes almost 50k a year as a teacher, but also has child support from both ex's and her parents pay for her rent in an upscale neighborhood as well as her car. Any emergency or special expenses were taken care of by her parents. As the months and years wore on, I noticed I was asked to take on more responsibility. By then I was hooked and the kids seemed to be quite fond of me, and despite them being spoiled, I of them. I am all for taking care of a woman whom I am dating. But this got to be too much. She has been provided with things her whole life and always either had a man or her family to provide for her. Her own father even admitted to me they made it too easy for her. She can throw real tantrums when she doesn't get her way or doesn't get enough attention. No matter where we went for upscale dinner/entertainment, trips, gifts, or help with her expenses, it never seemed quite enough. I spent a lot of time and effort trying to help and support her, but got very little in return. Most everytime we broke up, it was over something petty and I found myself miserable without her. Like a drug. Despite all the negativity about her, she also happened to be the funnest, wittiest, most intelligent, beautiful woman I've ever dated. Deep down she has a good heart, but her sense of entitlement drove me nuts. She really kept me on my toes, in a bad way. It was such a love/hate relationship. When we fought, it was epic. I normally tried to take the high road and ignore her when she was in drama mode. Eventually the right button was pushed and it was on. Screaming, name-calling, and it even got to become physical at times. Everytime we broke up, she moved on almost instantly. She cannot be alone. I noticed this pattern even prior to us dating. She has never had a healthy relationship and I don't even know if she knows what that's like. My family/friends all liked her, but didn't approve of how a 40 year old woman could be so dependent on others and were worried for me. I'm a self-aware man and realize how crazy it sounds on how a man clings on to a woman like this and still pines for her. I've always been confident, secure in myself and even- keeled prior to meeting her. I now find myself the exact opposite. I can't believe I wound up this way, thinking about her almost constantly. How do I shake this? I've tried counseling, dating, inviting God into my life. Nothing seems to help rid myself of this hot mess. HELP

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