Kate is up to her terrible plots
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Stiles falls through the floor in the Hale house and wakes up in Beacon Hills, 2005. The first time he stops Kate from interacting with Derek it's (more or less) an accident.
Every subsequent time isn't.
Derek has no idea who Stiles is, and Stiles would like to keep it that way... only, he's not exactly inconspicuous while following Derek around, now is he?