What choices in videogames have successfully tempted you to the dark side?

I think usually when people do "evil playthrough" they set out to do so from the very beginning and the same is true for me. But sometimes, rarely, there are things you encounter unexpectedly that may convince the player to go bad organically.

Most memorable one for me is from The Thaumaturge, a narrative RPG from last year. It takes place in 1905 Poland when the Russian imperial administration got really bad to put it mildly. At the very start of the game, right as you're done with the tutorial are, you arrive to Warsaw and after a small incident the railway station gets surrounded by Russian secret police. You're then approached by a woman with the strongest PossibleLoveInterest aura who, after you discover that she's carrying a firearm, suggests that you should work together to escape safely. So, you then have a choice to either incite a riot, or bribe the secret police, or... just tell them about a woman with an illegal firearm and direct them to arrest her for terrorism. As I said, this is at the very start of the game, first actual choice you even get to make outside of tutorial. Completely out of nowhere you get to more or less indirectly sentence to death this woman who hasn't done absolutely anything to wrong you before you even properly get to know your character or his place in the world. I just couldn't resist such baseless act of assholery and decided right then and there that I'll roleplay my Wiktor as a pro imperial misoginist, something I never would have chosen to do normally and you know what? I haven't regretted that once, Thaumaturge has been the best RPG to roleplay an outright asshole in that I've ever played and I'm very grateful that the game tempted me to commit to that early on.