When I got under the hood and started rebuilding this fantasy monstrosity that I'm re-writing, I figured that in the process of tightening up the storyline (desperately needed) and changing the underlying structure of the world (so things make more sense) I would eliminate some characters and their secondary storylines.
One wasn't so hard to let go. His name was Linker.
One of my MCs, Anders, originally had two friends and together they were the high-profile troublemakers on the local party circuit. (It's a fantasy story, but I figure some aspects of teenage life only change in the execution, not their essential nature...) The two friends were Theo and Linker.
Linker's side of the story became irrelevant due to the worldbuilding changes. And he was something of a jerk as well, so it was easy to give him the boot. To be fair, he did have some interesting moments and he put my heroine in some uncomfortable situations which I may need to recreate depending on how things work out down the line.
The remaining friend, Theo, will probably be put in that role. On the downside of eliminating Linker, it seems Theo has picked up a bit more jerkiness to compensate. We'll see how that plays out.
The more difficult character to drop was my heroine's younger brother, Klaus.
I liked Klaus. He was unfocused and kinda flighty and didn't fit in where he ought to. He got into a fair amount of trouble, needless to say. There was a nice, sharp moment where his actual relationship with Anders crashed up against their formal relationship -- in that Anders had to mete out some discipline as a master when they'd been acting more like friends. They both slunk away from that scene angry and hurt.
That won't be happening, now. I'm sorry to see it go (and some other fun stuff that Klaus was involved in) but there will be other good moments to take its place. His role can be filled by other characters and the point where he became an awkward problem will be eliminated.
To some degree, killing darlings does require confidence that you can write something else that's just as dramatically tasty as what you're cutting. Maybe the fact that I've got dozens of novels trunked away helps me with that -- while they're all essentially crap, they've all also got good moments in there. I've written tasty dramatic stuff before and I'll do it again. It's getting all the other parts up to par that's tricky...
You can cut good stuff. It will sting. But there will be more good stuff. What have you had to cut recently?