"You Remind Me of Someone I Used to Know" works as a callback to last season's "Some People Just Want To Watch The World Burn" as once again the Salvatore School prepares for its annual game against Mystic Falls High, although the new headmaster (Alexis Denisof) has a far more open mind towards his students using their powers, in moderation, to compete (which won't turn out well for one Mystic Falls student). The episode continues reversal of fortunes between the Saltzman sisters as Josie (Kaylee Bryant) continues down a darker path and Lizzie's (Jenny Boyd) bright outlook continues as she searches for clues about the mysterious Sebastian (Thomas Doherty).
The arrival of a new monster in the woods also leads to Hope's (Danielle Rose Russell) discovery that Rafael (Peyton 'Alex' Smith) is still a wolf. Queue up the impromptu team-up with Landon (Aria Shahghasemi) who discovers there is more going on with this oddly familiar girl than she's willing to let on. There are several takeaways here as Denisof's character is confirmed to be something more ominous than just an obnoxious headmaster, Josie takes steps down a dark path (which don't bode well for Hope now that she has volunteered to help Landon look into the mystery girl), and Rafael may be back but it appears it will take some time for him to fit back in the human world. I do think the show missed an opportunity by not allowing wolfboy to remember Hope, as reality was reset when he was in wolf form, but it appears that's not to be the case and if anyone is to learn the truth about her it will likely be by her own admission or through the trail of breadcrumbs he is leaving behind.
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