The key is in trying not to hurt him too much. There is no way you can avoid hurting him some, and the more you try the more convoluted things get and the worse it is when the end finally comes. He is hurt worse than he would have been, and you feel bad because you were "fond" if him some, not to mention all the extra time and energy you wasted trying to make it "easy" when you wanted just to dump him and get on with something else more interesting. Even though it isn't easy just to sit down and say "It's over." In the long run it is usually easier and "cleaner" than a long drawn out, event that just keeps pulling you back.
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