Sam:
Sam woke you up with a breakfast in bed. He kicked Dean out of the Bunker and made you your favourite dish. He lit candles and turned down the lights to make a romantic scene.

Dean:
You had been waiting to sit in the drivers seat of the impala for a long time. On your Anniversary, Dean let you drive the impala anywhere you want and he only hesitated to give you the keys for a few seconds.

Castiel:
You didn't expect him to know what an anniversary was or how to celebrate it but he must have gotten help from Sam and Dean. You had just gotten back fro the store and you smelled cookies. It turns out Cas had made cookies for you both. You cuddled up and watched romantic movies until you fell asleep.

Jack:
Jack brought you a bundle of roses and watched movies together.

Charlie:
You both got each other their favourite food. You spent the whole day snuggling on the couch together watching tv and playing video games.

Gabriel:
You can probably guess that Gabe got you a lot of chocolate. He let you choose wherever and whenever you wanted to go.

Lucifer:
He may be the Devil, but he's sure a softie when it comes to romance. You ate gourmet meals and he took the day off from killing and torturing and doing whatever the Devil does.