What's a way to be super manipulative and out-manipulate super manipulative my friend?

I feel like doing something slightly evil and teaching my friend a very valuable lesson. I have a couple plans but I need a few more. So what's a way to be super manipulative and out-manipulate super manipulative my friend?

What are some evil manipulative plans you can think of?

Umm...why would you want to do that? Did they do something bad?
But I'll say this anyway, you have to lead them the other way, they need to think that everything is okay, don't over do it, still act like you normally would, give no hints to what's comming he/she's way

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