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My ex and I were together for a year and a half... he was my first love. After we broke up, we tried to remain friends, but it was SO hard. I'd find myself getting mad at him because I thought I was the one who kept making an effort to remain friends and he wasn't trying. We'd have periods when we'd be friends, then not be friends, be friends, and not be friends. When we were friends, we'd hang out as friends but it usually ended in fooling around, which in the back of my mind I was always saying no, but I wasn't physically stopping it. This went on for a while, these whole on and off again friendship/hooking up stuff. Then one day when I was trying to talk to him, this was during our semi friendship, no hooking up time, he was like this isn't working, we can't be friends, we've just grown apart. I got really upset and couldn't believe he wanted to cut off all ties, but after a while that feeling just faded and he was just out of my life. It wasn't until recently that we've started being friends again... but since he had hurt me so much when he said those things and I got so used to him not being in my life, that when he initiated communication, I was just like whatever, I'll talk to you, but at this point it really doesn't matter if we have a friendship to me. I didn't say these things, just felt them. So we still talk every now and then, but now I'm kinda numb, and don't really care either way if he stays in my life or not. It's kinda sad, but it's true.
ETA: And as far as when do you ask if he's seeing anyone, he actually asked me that recently... he's asked once before, but we got side tracked and I had never answered him. I felt awkward when he asked me, even though I wasn't seeing anyone. I asked him if he was and he said no. I didn't really care either way, but I figured I may as well shoot the question back at him.
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