(please share your own here as well because i only have 2 right now that aren't just "what if" prompts)
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if you have a big cast or cast with lots of side characters like i do, take your whole list of characters (or a decent amount of them), plug them in here, set it to "generate groups by number of names per team" and 2. no matter who ends up with who, either come up with a trait that those two characters share (beyond just "they both know so-and-so" or "they both live in [somewhere]", OR write a little scene between those two characters.
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go to tv tropes (you know i love tv tropes) and press the "random trope" button at the top of the screen. think "who/what does this apply to in my story?" "who/what could this easily apply to without any drastic changes to my story or characters as they presently are?" if the answer is nobody and nothing, you don't have to try to fit a square peg in a round hole, but for me, this exercise helps bring light to a lot of appropriate narrative choices that i might otherwise ignore.