Breaking up almost always sucks no matter which side of the equation you find yourself on (abusive relationships being sometimes, though not always, the exception). If you are doing the breaking, you've basically got to have some sort of confrontation with someone you cared about (and perhaps still care about) that you know will hurt their feelings, at a bare minimum. If you're being broken up with, someone you care about is telling you that your feelings are not and won't be requited, and that singlehood is preferable to your company, no matter how little commitment or emotional attachment there actually is.
I am old enough and have dated enough to have been on both sides of this ugly divide —and have made enough poor choices to have been subjected to some (in retrospect) pretty hilarious dumping scenes. So, if you are absolutely incapable of ending a relationship with dignity, mutual respect and honesty, at least try not to do it any of the following ways that were done to me.
10. "My mom doesn't like me dating white girls."
9. "My [cult leader] says I can't keep dating you unless you join, so how about, for our next date, we attend a meeting?"
8. "My boyfriend isn't comfortable with us getting any more serious."
7. [That's radio silence after dating for a while.]
6. "I just can't handle any drama in my life right now."
5. "I just don't feel like you're that into me any more."
4. "When I said I wasn't ready to be exclusive, I meant I wanted to have sex with other people. That didn't mean you could!"
3. "I just really think I deserve someone thinner and prettier."
2. "Hey, so, just so you know, last night, I totally fucked this other girl, I just wanted to let you know before anyone else at this party did, since they were all there when we started hooking up."
1. And, presenting in graphic form, the ugliest way anyone ever dumped me:
Images via RYN TMRW on Flickr, Creative Commons licensed and me, with help from someecards.