Not just making characters cry in general, but a sadistic kidnapper holding hostage a damsel in distress and making her cry because her attempt on his life failed... It's complicated. I don't like making undeserving people suffer, that's the short version. I can make people cry, but I don't like to, so whenever I play any sort of villain I have difficulty making them really "evil" without feeling bad about it. Don't ask me why, 'cause I dunno. I can be bad, but I don't enjoy it.
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The more I stare at that eye the more creeped out I get. Pretending that it's a horse makes me feel a little less creeped out.
Ha, you remind me of another RP friend, she always makes her characters suffer emotionally all the time. I can't play characters like that, or if I do it's really hard for me to stick to their story. I just can't be sullen for a long period of time, maybe I could if I tried really hard. It's like Griffin, he's a cranky hermit who hates people, but he's not really evil like the kidnapper is (I guess I should come up with a name for him eventually). Griffin actually amuses me greatly, whereas I have a strong dislike for the other guy and it all comes down to their intentions, their motives.
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During my beginnings on this site, I got so obsessed with making characters depressed (usually my own) that it actually got on other people's nerves rather often. I've since learned to turn it down but I do still very much enjoy character misery when enjoyed properly in moderation.
The way I can do it is because I come up with a complete life story for a character. Seriously, I could write a novel on just their history alone. It's all in my noggin. Then I just reflect on that history to shape their behavior, and then as they are influenced by outside things, their behavior will begin to change. It's more realistic than having a character that is perfect in every way, or has a few flaws but is not really emotionally affected by them. Also, I don't take it overboard where it's just a constant sob-story, because that's annoying. I do that by not revealing all of the flaws, or specifically stating what the character is thinking or feeling. I leave a lot up to interpretation, but I'm not sure if people look deeper into my writing or not. If they want the whole story, they should. xD
That's another factor when I create a character, I try to avoid the "bad childhood leading to messed-up adulthood" backstory because I see it too often, it's not really something unique or at least it doesn't seem that way. If I have to be a villainous character, I'm more likely to make them a "good-person-turned-bad" for whatever reason.
Oh yah, I get that. I could tell you the childhood of every one of my characters, knowing their entire history makes them seem much more real instead of them just being information on a character sheet. I know what they're thinking constantly, what trains of thought lead them into whatever actions they take. Most of the time, writer's block happens to me when I can't figure out what my character is thinking, I have to figure that out first so I can keep them in character and not have them change into someone totally different.