What is Tom Sawyered?
1.
To be convinced that something that is to your benefit is actually harming you. This is similar to when Tom Sawyer convinces the neighborhood kids that his chore of whitewashing a fence is actually the most fun thing ever, to the point of getting items for letting them do his dirty work for him.
Me: I got played by this guy pretending to be a hot chick, but I convinced him that I was leading him along the whole time instead.
Friend: You totally Tom Sawyered that dumbass!
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