Oh yeah I've broken up with friends lots of times. The most recent was My friend @Speedforce@multiverse.soulism.net. She was making Herself absolutely miserable and using Me as an excuse for Her depression. She said I wanted Her to be dependent on Me. So I told Her I'm gonna prove that's not true by kicking Her out of My life.
Once She ran out of excuses to be sad, She toughed up and went and had some fun. Now She has meatspace friends and an optimistic attitude. And we're slowly exploring maybe being friends again. We're not there yet, but we might be in a few weeks or months.
That's the best a friend breakup has ever gone for Me. I've had a lot of worse ones. I can tell some really sad stories and some deeply sickening ones.