Original Generation:
Harry-
A quiet night settled around Hogwarts in anticipation for the special day arriving the next morning. You relaxed in your dormitory, you were the only one there with all your friends off with their boyfriends. Your boyfriend, Harry, had said he was tired and went up to sleep. You didn't mind much. It stung a little, thinking this was your first Valentines Day together, but you weren't even sure if you two were official. He'd been too nervous to hold your hand. The closest you'd gotten was resting your hand on the edge of your chair, and his on the edge of his, the two of your hands touching just slightly. It made you blush a little, but some days you'd wish for more. You lay on your bed with a book, snacking on a large box of chocolates you'd received earlier that day from your sister. She had graduated two years ago, and would be busy with church and a date with her husband for Valentines Day.
There was another knock at your window, particularly loud. For a moment you thought it was another owl that'd crashed into the window by accident. A different flying creature waited outside the window. Harry looked rather sheepish for unintentionally hitting your window so hard, and possibly alerting the other girls of his presence. You didn't even bother to bookmark your page and leapt off the bed to rush to the window, causing a piece of half eaten chocolate to roll onto the floor.
Without even a word in edgewise, you were swept away from your room. You squealed from being to high in the air, but Harry held onto you tight. As he flew to some unknown location far from the castle with a grin on his face you couldn't help but think this was much better than holding hands. Neither you or Harry were seen in the castle until late into Valentines Day, both rather tired eyed but with fond smiles and candies and gifts tucked deep into you pockets.
Ron-
Ron waited for at least two hours on the Quidditch pitch. It was where you went whenever you were frustrated, and after his sudden disappearance you were bound to be angry. He started to get nervous, waiting in front of the grass with your broom and his own in his hands. His trick may have worked too well. He worried you'd thought he'd ditched you and you'd gone back to your room upset. It was meant to be a harmless ploy, but now Ron was starting to see flaws in his plan that could turn badly. He went to leave the pitch when his hand wrenched away from him. Your broom launched itself backwards towards the pitch and reflexively he pulled it back. He was surprised even more when it moved again. He tried to set it on the ground again, hoping that would stop any accidental commands he'd given it. It didn't stop, and the broom handle slipped from his hand and flew quickly back to the field. He mounted his own broom at set after it, not even thinking for a moment what was causing it to move. He was too preoccupied. You loved that broom and he couldn't lose it to some magical 'glitch'. The wind beat against his unguarded face and it felt like being close to a fire, the friction of his body against the air become to intense as he chased the broom in circles. As if on cue with his thoughts the broom set ablaze. It stopped flying and he had to wrench away to avoid running face first into the blazing broom. It fell to the ground and Ron couldn't believe that your favorite object in the world was just destroyed before his eyes. Before hitting the ground it started moving again, straight for the message he'd spent hours writing in the grass. The fire spread to the grass but did not move past where the broom touched. He sighed and almost laughed, realizing how ridiculous this whole thing had been. In the grass, new books he'd bought and laid out in a wonky heart shape were untouched. The fire glazed in certain spots of the grass, but the grass itself did not burn. Ron had to move to see the new message left behind. A blazing heart with 'you too doofus' directly next to it. The broom had long disappeared to join you hiding in the stands, and you approached Ron to surprise him yet again, but with a hug instead.
Draco-
No surprises, no big presents. Just the way you wanted it to be. Laying your head against Draco's shoulder. Intertwining your hand with his. Staring into the docile fire. Smelling the incense lit somewhere far away in the common room. Whispering quietly. Occasionally moving your head to kiss him or look into his eyes. Feeling at peace. With the world slowing around you. The air full of love. No wars, no Voldermort. Just plain old love. Just plain old life, simple and comfortable. Lovely. You wished it could last like this forever, and it seemed to be just that as you stayed together,enjoying the muggle holiday. Love could conquer all, you truly believed that in that moment.
Neville-
You could tell Neville was struggling to plan something. He always wanted things to be perfect, especially when it came to you. You wanted to take over the Valentines Day plans instead, but didn't want to spoil the surprise. The day before he was noticeably stressed. You insisted on doing something with him. You dragged him out of his room, which he wouldn't let you see inside of, and down the stairs and out of the common room. The halls were mostly empty, dinner was over and curfew was coming soon. You took him out of the castle, and in the distance he could see one of his favorite places. The Herbology greenhouses. You took him inside, a planting pot with a bag of dirt and seeds beside it.
"Come plant these with me," You said, going over to the pot and filling it with dirt.
There were dozens of bags of seeds along the table.
"Which one?" You asked. His eyes seemed a lot brighter.
"Pink carnation," He said.
"Are those pretty?"
"I have no idea," His smile was bright and he looked you deep in the eyes. "But I read that they symbolize love."
"I think those would be perfect," You said, finishing up with the dirt and using your hands to dig a hole for the seed.
"Use gloves (Y/N)," Neville said. "You're getting dirty."
"Afraid to get your hands dirty?" You teased.
He smirked, getting his hand dirty with some dirt from the bag and smearing it on your face. You frowned angrily at him before using both of your hands to create large smears on his cheeks.
"You got mud on your face you big disgrace," You sang. Neville didn't get it, but he laughed anyway.
Fred-
A parchment rustled quietly on Fred's desk. It was blank and ordinary, folded into three pieces with the middle piece twice as big as either of the side ones. Nonetheless, it had an air of adventure to it and the breeze that came from the open window gave it a sense of life that seemed to be more than just that of an inanimate object. Besides, nothing Fred had was just ordinary. You did everything you could to reveal the secret of the paper. Spells and incantations and even throwing the paper across the room in frustration.
"I solemnly swear I am up to no good." Fred called from beyond the door. You hadn't seen him there, and he probably wasn't happy with you messing with his stuff, especially with his cryptic language.
You rushed to put the paper back and tried to play it off, but you noticed it moving. It was magic! Ink spilled across the page from some unknown place and on it you could see the words 'Marauders Map' appear on the front. You'd heard so many stories, you knew Fred was bound to have it. On it, you could see all the students of Hogwarts, their footprints mapped out on their location, fading in and out as they moved around. You could see your footprints and Fred's. His moved around the room in a seemingly random motion. Mesmerized, you watched the ink fade and reappear. The footprints lead away from you and across the room, then back again. They stopped moving right behind you. You set the map down on the table and turned back to him. His face was as red as his hair. He pursed him lips and licked them a bit until settling on a happy grin. You look at him confused, and as your eyes traveled to try and understand the situation you saw Fred was on his knee. Only one knee. With a dark felt box in his hands which he held out to you. You put your hands to your mouth and almost began crying. He couldn't even say anything before you'd fell to your knees and wrapped your arms around his neck. Tears streamed down your cheeks and you couldn't stop smiling.
"Yes, yes, yes," You said, not able to think of a better word.
He stood, picking you up and spinning you around in his arms. You pulled away only a little bit to kiss him.
George-
A box of chocolates was enough for you. George knew that. But that wasn't stopping him from going all out. You were just glad he'd been subtle about it. Well, subtler than he usually was. The day started with an owl by your window, a parchment on it's leg with a cheesy message written in black ink on it.
"You will never again have to ask what the best thing in my life is, because it's the first word of this sentence."
Then a box of chocolates at breakfast with the post. It was tagged from a secret admirer, in George's handwriting. To which he jokingly claimed you were cheating on him.
A note in your potions book saying "I'm yours".
A firework set off at lunch in the shape of a heart. Unfortunately, it also caused the enchanted ceiling to rain. But you didn't really mind.
You were absolutely done when you got back to the common room after class. An over-sized teddy bear, larger than even Hagrid, was left behind with your initials on them. You couldn't shake off the laughs. George always ends in a large finale, you knew this. But what he did in your dormitory somehow was even bigger than the teddy bear. You'd shrunk it down and carried it in your pocket, but the weight of embarrassment was much less when you saw his next charade. You don't even know how he got up to your room without setting of the staircase.
Strings of dozens of papers and photos hung from the ceiling. You could barely see any other contents in the room. You traveled slowly through the field of papers. Dozens, if not hundreds, of moving photos of you and George. Closest to the doors were the earliest photos, of your first year together. Then on to your second and third and fourth, and finally ending on the seventh. The latest photo of you was just barely of this morning, from all the gifts he'd given you. Even ones you'd gotten in rooms he hadn't been in. At the end was a large canvas. It hung about halfway down the room and you couldn't help but step through the slit cut through it to make and opening. There were even more pictures, condensed so much you couldn't even tell where in the room you were. Pictures of various houses, beaches, cities you'd never been to, and lastly wedding photos. Dresses and flowers and cakes and rings. In front of one of the pictures hung an actual ring. Thin and simple, with a small diamond embedded into the silver metal with your initials engraved on it next to George's, with only one small change. You're last initial was changed to W, for Weasley.
You gasped and looked around to find George. He sat on your bed, directly across from the ring. He stood up to take the ring of the string it hung from and kneeled down.
"(Y/N), at the beginning of the room was all the time we'd been together. From third year until now. Through hundreds of days and weeks together. I love you more than anything, and I really hope that these pictures could be our future."
"No more giant teddy bears?" You laughed a bit through your tears.
"No promises."
You faked a frown, but let him but the ring on your hand. It felt sparkly. Like happiness melted into steel. The happiest moment in your life. You hugged George tightly, and over his shoulder you could see more pictures you didn't see before. Baby clothes and cribs and diapers. You hugged him tighter. It was the perfect future, the one you always wanted.
Marauders Generation:
James-
James was an absolutely ridiculous baby, you knew that much. But you didn't think he'd actually go so far as dressing as a baby. He stood in the Gryffindor common room in a white robe covering only half his chest and his waist. He held a bow and arrow in his hand, with a heart shaped head on the end of the arrow. You stifled back a laugh as he attempted to load the bow to shoot you with the love arrow.
"Need help lover boy?" You said smugly.
"I'm a lover baby thank you very much."
"You are indeed a big baby."
"Screw you (Y/N), I'm trying to be romantic here."
Before you could say a comeback the notched arrow was loosed from its bow. James reached out in panic and the arrow flew directly into you face. It painfully poked your eye and you doubled over, holding your hand over your eye.
"Bloody hell! I'm so sorry." He bent over, dropping his bow, and reached for your face to inspect your eye. It stung and you could feel the blood throbbing against you temple.
"Now you're definitely not going to screw me." You tried to lighten the mood. James looked absolutely miserable, he really felt bad for messing up Valentines Day. You hoped this might lead him away from such cheesy stunts, that was just about the only upside.
"We should go see Madam Pomfrey."
"I'm fine," You insisted. You really didn't want to blow this out of proportion.
"You're not. I want to help me."
You grinned cheekily. "Kiss is better?"
James couldn't resist smiling anymore. He did in fact kiss your eye, which actually made it worse, but you didn't tell him that. Moony fixed it, and you got to spend the rest of the day with James. But only after you made him change out of the cherub outfit.
Sirius-
A rap song. A bloody rap song. You knew Sirius liked muggle music, and you did even more than he, but this was far too much. He was just trying to embarrass you, there was no other explanation. He had no shame, but you on the other hand were awkward and incapable of handling situations like this. He purposefully brought together the cheesiest and worst lines imaginable.
Even if you were a smoker you couldn't be more smoking hot
You're not the kind to be caught with pot
This is a cheesy day
How could muggles not be swayed
Into making this illegal
To top myself from last year I'll have to buy you a .... beagle
I just hope you don't get too obsessed with my like Smeagol
And that weird necklace or something from that one movie
Bloody hell I thought you would have stopped me by now
His cheeks started to turn red and you just stayed silent, watching people begin to laugh around him. It was kinda enjoyable to see him embarrassed to once. You felt pretty silly too, but it was worth it.
Remus-
You couldn't believe you had been dragged into detention. It was all Sirius's fault for mentioning you when he was being interrogated about one of his latest pranks. Of all the days, you'd been forced to spend hours in Filch's office cleaning things for his cat on Valentines Day. You'd missed an entire day of plans with Remus and you felt horrible about it. He had been so excited to spend some genuine alone time with him. Tiredly you left for your room. When you opened the door a shadow at the other side moved. You whipped your wand out, knowing none of your room mates would be there. Remus put his hands up quickly in defense and with a sigh you tucked your wand away. You were too tired to scold him for it.
"How'd you get up here?" You wondered quietly as you set your stuff down. He didn't provide an explanation, but it wasn't all to important to you.
"How was detention?" He asked awkwardly. He could tell you were tired and wasn't sure how to proceed. He had something planned for you, but it just didn't seem like the right time.
"Hellish," You said. "But I'm glad I didn't miss the entire day with you." You smiled past your tired eyes and hugged him.
"I have something for you," He said quietly into your shoulder, almost unsure whether or not to let you hear him.
"You shouldn't have."
"I was going to anyway."
He pulled back your lumpy bed covers to reveal an array of books spread across them. Remus whispered quietly behind you, nervously cracking his knuckles as he looked hopefully between you and the covers. His words, quiet and indistinguishable as they were, were speaking along with the titles.
'Love is Sweet' 'E.R.' 'With You' 'Ahnd' 'Me Together with Chocolate'
You sighed but couldn't help but smile. "Is that a pun?"
"Only if that earns me bonus points."
"Even one book would have gotten you bonus points."
You cuddled together in bed, reading together one of the books Remus had bought. You rested your head on his shoulder as you opened the book to begin.
"I love you," You said, placing a kiss on his cheek and turning back to the book. He kissed your head and wrapped his arm around you.
Next Generation:
Albus Potter-
After the battle of Hogwarts, a lot more muggleborn students came to Hogwarts. With this Hogwarts had school off for a lot of holidays. With the end of the semester, Valentines Day came, and the students were allowed an entire week off. You couldn't have been more happy. You parents were in India on a religious retreat, so you got to come home to a different home. It was home nonetheless. The same town, the same people living in it. Though your looks on it changed on the train ride. You sat next to Albus, holding his hand, thinking about what it would be like to spend time at his house, with his family. You already knew about half of his family, as they went to school with you. But you hadn't met any of the adults yet, and that scared the bonkers out of you. You'd be meeting the famous Harry Potter, not to mention Hermione Weasley, Ron Weasley, Ginny Potter, George Weasley, and his dozens of other family member who famously fought in the war.
Strangely enough they were surprisingly nice. You found it easy to become comfortable with them, make jokes and just have fun. They reminded you a lot of Albus, which is probably where he got it from. He took you to a carnival, to try cotton candy for the first time and ride a roller coaster. You held onto his hand the entire time. The crowds were immense and the rides made your stomach lurch. He kept the souvenir pictures they sold of the roller coaster ride, especially one of you screaming as the ride made an almost vertical drop. You'd tried to rip it, but sadly failed, and he laughed at you, much to your distaste. On your way out, right as all his relatives were looking, he made a point to kiss you. Earning some wolf whistles and loud groans. You were surprised, but took the moment to steal the picture his hand and ran into the front seat of one of the cars and drove off. Unfortunately, his dad, who was in the car, made you drive back for Albus. But he never did find the picture, neither could you. His dad took it.
(A/N I finished this late on Sunday. I realize that many of you are in different timezones and might even get this update Monday morning. Nonetheless, I hope you had a wonderful Valentines Day even if you were only accompanied by fictional characters (like me). I hope you all enjoyed this chapter.)