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Originally Posted by Infinite_Loser
The problem is that I find it next to impossible to break it off with her, partly because I've known her for such a long time and partly because she makes me feel so bad whenever I'm about to do it.
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When you do go to break up with her, you need to just get it out... don't give her a chance to respond until you've said your piece. Keep it short, simple and just get the point across that you don't want to be in a relationship with her. After that... you can worry about her hurt feelings and your guilt, and the healing process can begin.