Most likely to...(TVD)

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Have a big surprise ready only for it to be ruined by one miniscule detail:  Stefan. He would have the surprise itself all figured out, I feel like delivering the surprise would go wrong, like he would forget what time you got home or something.

Wake you up in the middle of the night because they can't sleep: Damon and Kai. Both boys have absolutely no problem annoying you.

Drunkenly sing a karaoke ballad for you in front of a crowd: Damon. He drinks more often than pretty much any other character, so statistically he is the most likely. Not to mention he likes to be the center of attention.

Buy you an entire litter of puppies: Stefan. He will go to great lengths to make you happy. And hey, if you don't like them, he can eat them.

Compel your bully to embarrass themselves publicly: Enzo, Rebekah, and Caroline. Rebekah would be the most outgoing with her idea, you'd have to stop her and make her change it to something not dangerous. Enzo would probably compel them to apologize and be your personal servant for a while. Caroline would compel them to do something embarrassing and then compel them to leave you alone.

Pick you up from school claiming they're your older sibling: Marcel. He would know how to talk to administration, and he's fun loving enough to do it even if it's not for your safety.

Suggest getting couple tattoos: Elena, she likes doing spontaneous things once in a blue moon (like dying red streaks in her hair) But she would also do it as a way of saying that you would be together forever.

Hold something embarrassing over your head for years: Klaus. He does not let things go even if they're irrelevant, it's just in his nature.

Become a stripper because you said they should as a joke: Silas. That man has so much confidence and zero shame, and is not one to back down from a challenge.

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