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Once I get to the point where I'm 'done' with someone, usually I'll try and make an effort to tell them precisely why I'm done with them. Then, if they claim to have fixed those issues, great, I'll give them a second chance. If they repeat the same problems, I'm very done with them then. The unfortunate reality though has been that even with the second chance and such, the other person tends to have that personality quirk/trait/issue/subscription already ingrained, so the likelihood is that there isn't any 'easy' fix for the problem that caused the rift in the first place. So, it takes a lot to convince me that there's a solid, reliable reason to keep trying again and again to help them fix it since they clearly can't or won't on their own.
Other times, when things just aren't 'working' right between myself and someone, I'll just take a leave of absence for a while, trying to step back and see what's going on with me, to figure out where my issues are coming from. If they're things that seemingly can be fixed I'll reenter with a few choice conversations about what and why, and see what happens. If not, then I usually don't bother. Life is too short, after all.