Ciel-
Ciel finds Valentine's Day foolish and idiotic, yet it's one of the days where his company gets the most profit. Sebastian kinda forces him to go on a date with you, he does this by not only inviting you over without telling Ciel but having a romantic candlelight dinner prepared for the both of you. Ciel wants to kill Sebastian (but he can't), while you're so happy to spend Valentine's Day with Ciel...Ciel, not so much. Though he does eventually get over his bitterness and actually does...kinda have a nice time with you. You didn't know what to get him, (because he has frickin' everything) so you have him a sketchbook. He's absolutely baffled, but you tell him to open it and after some back and forth he opens it to see every picture you ever drew of him. You even tried some of you being together, you honestly didn't expect anything back but Sebastian comes wooshing out of nowhere with his gift for you, and it's a little locket with two pictures you took together with a proffessional photographer. You're so excited about it and ask Ciel to put it around your neck, he reluctantly does so before your carriage arrives and you give him a big hug before leaving, Ciel is frozen for a minute after you left before regaining his senses and becoming very, very flustered.
Sebastian-
Sebastian is actually very romantic on Valentine's Day and he asks the Master for the day off and takes you to a nice restaurant. These kinds of dates are very rare, but are enjoyable nonetheless. You vent, talk and laugh with each other at some of the stories you guys tell. He got you a nice pair of earrings, which you can't help but admire. You also got him a new pocket watch, it was the latest model and it was more accurate than ever, which he deeply appreciates. Then you'll go back to the manor and....let's say you won't be able to walk for a few days...
Finnian-
Finnian loves Valentine's Day because now he has you to celebrate. He really does try to be romantic, even asking for advice and help from Mei-rin and Baldroy on what to do. They eventually came up with an idea of Finnian taking you out on a picnic date. Mei-rin helped Baldroy pack a picnic basket full off sandwiches and other picnicy foods for you and Finnian to eat. Finnian is so excited when he asks you to go, your first thing is to ask the Young Master if you could go with Finnian, but he reassures you he already has it covered. At first you and Finnian talk and laugh but you eventually end up pouring your hearts out to each other while you both give each other little hand squeezes and hugs. You consider Finnian preparing this amazing date for you a Valentine's Day present so you give him something better, your first kiss. The whole way home Finnian is secretly freaking out but before you go your separate ways he gives you a kiss back before wishing you goodnight and booking it down the hall from how nervous he is.