Midoriya-
Midoriya loves Valentine's day, but he wasn't really popular with the girls so his past Valentine's Days have basically been nights full of tears, rom coms and ice cream. Tho he's more likely to cry at the rom coms than anything else. He's very shy and nervous because it's your first Valentine's Day together and he wants to make you feel special but doesn't want to be too over the top he scares you away. He asks you out by basically running up to you and shouting about if he could take you out after school on the special day while bowing a bunch of times, it was the same when he confessed to you but it's still embarrassing as hell. You do confirm that your available and he shouts his thanks before running off, everyone will turn to you and go 'ooooo' with teasing smirks, even if they're not from your class. He gets you this really big bouquet of flowers and is repeating his compliments to you so he doesn't accidentally forget them and blank out like he usually does. Then he sees you in your dress and his face turns so red and he's so flustered he can barely say anything himself, though he looks super handsome because Aoyama absolutely insisted on doing his hair and it actually came out really well. After you put the flower bouquet he got you in some water he'll take you to a nice restaurant that his Mom recommended to him. At first he tried not to mention hero stuff because it's a special date and he was told by several of his friends not to talk about it, but you tell him that it's alright and he basically recaps the last few days of hero training and how cool it was. You add in your little thoughts here and there but you honestly find it adorable how passionate he can get. He got you a super cute plushie of your favorite character/hero. You got him this All Might pin that he didn't have in his collection from like, ten years ago. He's super excited because his All Might pin collection is finally complete! He gives you the tightest hug ever and is almost about to cry, again. So all in all, it's a pretty great Valentine's Day.
Bakugou-
Bakugou thinks Valentine's Day is stupid, he'll show you affection how he wants when he wants, no damn holiday is gonna tell him what to do. At least that's what he says. He gives off the impression that he doesn't want to even hear about Valentine's Day and whenever the other couples in your class talk about it you just kinda look at Bakugou and he just goes 'tch' and turns his head. You respect that he doesn't want to celebrate the holiday but he could at least show some interest, you get really sad and the singles in your class are like 'hey, if you don't have any plans you could always join us for romcoms. Midoryia's bringing ice cream' and you agree to go because you don't want to be alone. Though Bakugou can tell your getting upset and invites you to the arcade for a date that just so happens to be on Valentine's Day but tells you it isn't because of Valentine's Day or anything and you get so excited. You can't help but keep smiling the whole day before you two go to the arcade. You guys mostly banter about who's gonna beat who but Bakugou wins, he always wins. Not that you mind, you just like spending time with him. Tho he uses his tickets to get this plushie of your favorite anime character that he may or may not be jealous of because you commented that he was kinda cute once. You didn't really have anything for him and you feel kinda bad so you give him a kiss, it's kinda like all the kisses you've had with Bakugou but he's more passionate this time. Which is kinda sorta a little too much for the public but he flips off anyone who even tries to say something to you as you kinda sorta make out by the arcade.
Todoroki-
Todoroki likes Valentine's Day but he doesn't overly love it, he's never had a real reason to celebrate it but he does sometimes wish he had someone to celebrate it with as of late but never did, until you. So he goes all out for this, hanging paper lanterns in a small area in the woods and lighting them with his quirk, getting special dining chairs and a table with a fancy table cloth and candles. He has the menu be your favorite everything, from drinks to dessert. He also convinces Natsuo to be his waiter because let's be honest here, if it weren't for Shouto asking him to waiter for you guys he would most likely be at home and watch 'Your Lie in April' while crying his eyes out because he doesn't have a Valentine. You're really surprised that Todoroki would go through all this trouble for you and you just keep looking around wordlessly. This gives Todoroki a lot of anxiety because he's worried that you don't like it so he asks you if everything's ok and you tell him that you still can't believe he did all this for you and he says with 100% seriousness 'of course I would, I love you and I would do this every day if you wanted me to' and in the background you could hear Natsuo say 'please don't' aaaannnndddd now your face is really red b/c even after all this time it's still hard to believe such a handsome and amazing person like Todoroki fell in love with you. Todoroki's used to you blushing, embarrassed by his seemingly random times he says those three special words to you. He's about to make you turn even redder with his over the top gift for you. Remember that several thousand dollar drawing computer that you wanted? He got it for you. You're both really embarrassed, surprised and thankful. Though you tell him that it's too much he insists that you take it and you reluctantly do. Your gift for him isn't as expensive but it still has a lot of thought to it. You made him a photo collage of every picture you two took together in the shape of a heart. Todoroki just freezes up before suddenly hugging you because he loves it so much. The next time you see his room you find your collage hung up by his bed and you're just like 'wut???' and Todoroki's like 'it helps me calm down when I get nightmares' and you're just like 'wut?' and it's basically back and forth like that for an hour until Fuyumi shouts 'damn it (Y/N)! He loves you ok?! You gotta accept that!'
Shinsou-
Shinsou, like Bakugou, doesn't believe in Valentine's Day but will still take you out just because. It would most likely be a movie because you're a big fan of movies and there's this old but classic rom com showing nearby and Shinsou's just like 'eh might as well' it's kinda a classic movie date where he puts his arm around your shoulders and you share popcorn but that's kinda like, every movie date too. It's still nice though, and the difference of this time than the others is you guys actually kiss halfway through. It's just a pleasant, simple, 'I love you' kind of kiss. It's the kind of kiss that makes you smile at each other before returning your attention the movie as you cuddle just a little bit closer. After the movie, Shinsou will walk you back to your house as you just casually talk about whatever comes to mind. Shinsou's gift is pretty standard but with a little twist, he got you Valentine's Day candy but he opened it and got rid of all the chocolates you don't want while replacing it with the ones you like and updating the guide that always comes with the boxes. You love it and give him a big hug before telling him to wait at the front of your house before running inside. He'll wait because he knows you have something special, and you do. You got him a limited edition Eraserhead Pop! Figurine because you're one of the few people who know about his adoration for Class 1-A's teacher. You also got him a cute black cat phone charm because he said those were his favorite animal. You get so happy and surprised everytime you see his phone now because he has the charm there, you're just not used to people actually using the stuff you get them.
Kirishima-
Kirishima thinks it's totally unmanly to not do something for you on Valentine's Day, so he'll do something that he claims is 'totally manly!' He takes you to a rollercoaster park nearby and you're just like 'ok...this isn't the weirdest Valentine's date I've been on, I'll try it'. You spend the first few hours just riding rollercoasters together, tho you have one requirement for every rollercoaster you go on, no more than one loopty loop. It cuts out a lot of the rides but you still have plenty to go on, though towards the end you and Kiri get really naseuous and you have to just sit on a bench and try to get the world to stop spinning for like, at least 30 minutes. You both are so zonked out you don't even say anything, which is weird because you're like, the most talkative couple ever. After those 30 minutes you decide to stay on the ground, eating amusement park food, him trying to win the games to try to impress you (you eventually find the Bakusquad and Bakugou wins you the stuffed animal you want without a problem) it makes Kiri super motivated to try to get you the biggest prize ever. He does eventually win you a giant shark plush that you can barely carry by yourself. You kinda sorta end up using this as your bed now. You got him several different headbands, all of them being super cool and some of them were ones he was trying to find but never could. He's really excited and wears all of them, and like Shinsou, your both happy and surprised that he wears something you got him and he's all like 'of course I would (Y/N), it would be totally unmanly of me if I didn't wear the stuff my girlfriend got me.'
Tokoyami-
Tokoyami's on the fence about Valentine's Day, on the one hand it's nice to have a day to celebrate with your partner, but on the other he thinks that people shouldn't feel obligated to show extra special attention to their partner for a special day and sees it as a way for bad partners to keep stringing their S/Os around for another year. Which is one of Tokoyami's insecurities with you, he's afraid that he's being a bad partner to you from his lack of physical affection and cold-ish attitude to you, though it's all in his head because he's plenty affectionate and warm to you. For Valentine's Day, Tokoyami doesn't know what to do with you for Valentine's Day because well...he's never had a girlfriend before. So, he takes you to a rom com showing in a nearby theater and go for froyo after. It's simple but nice, and since you both are movie buffs you talk about the pros and cons of the movie. Like if the writing was good, if it was right to have the main couple fight when they did, that stuff. Though the next day you'll totally drag him to the store to get discounted Valentine's Day candy. Your present for him is you found this hoodie for Tokoyami to use when it's really cold because last time there was a snowstorm he looked like a giant black marshmallow with the coat he had b/c it was one of those super puffy ones. So the hoodie will totally help him out with less public embarrassment. Oh and he got you a black hoodie too. But it's different than the one you got for him because it's super soft inside because he knows how much you like super soft things.
Calamari-
Calamari loves Valentine's Day, and he's super experienced at what to do because he was a playboy, that changed when he met you. Despite his experience with other Valentine's Days those girls don't matter to him like you do. So he begs his friends for help, but Bakugou and Kirishima already have plans, but Sero and Mina are totally free! They help Denki come up with an awesome idea, roller blading. Denki's hesitant because he hasn't done it since he was four for a Talent Show (he made sure to burn the tape when he befriended Mina). But it's worth a shot and asks you, to which you eagerly say yes. You used to do it a lot in middle school with your friends but when you got to U.A you didn't have as much time as you used to. So you go to the roller rink and Denki totally falls on his butt and crashes into walls like, a thousand times. And you're like 'you aren't experienced are you?' and Denki's like 'noo...hehe...' so you help teach him how to skate for the rest of the time you're there and he's a little shaky but finally gets the hang of it. He apologizes a ton during and after you hang out at the roller rink because he was totally useless, if anything he wanted to be the one to be teaching you. You insist that you don't mind teaching him and that you could go next weekend so you both could have a fun time while knowing what you're doing, which Denki totally agrees to. Of course what's a Valentine's Day with Denki without a little kissing? You swear it was meant to be a goodbye kiss after you gave him a new pair of headphones that he expressed to you that he needed several times. But nothing's a quick kiss for him, so after he gave you this really cute and floofy dog plushie and he got your gift. You kinda, sorta, ended up making out on your front doorstep. If it wasn't for your Dad being like 'nope' and dragging you inside you probably would've made out for a lot longer. Now some of your neighbors ask how you and your boyfriend are doing and stuff because they saw you two making out, it's really embarrassing.
Iida-
Iida is very passionate about Valentine's Day, but not in the way you think. He's passionate in a way that he wants to make Valentine's Day absolutely perfect. He'll take you to a fancy restaurant where you'll accidentally do something stupid at least twice because it's so damn fancy, then after a very long and delicious meal he'll take you on a walk at a nearby park at night. Where he'll ask you for a dance and you're like 'but, there's no music though...' and all of the singles of your class just pop out of the bushes with instruments and just start playing. You're both surprised and not at the same time because this is Iida we're talking about, he goes over the top with everything. But, you didn't think he could convince every single in your class to do this for you guys. He teaches you how to properly ballroom dance and you're so into the moment you don't notice your friends stop playing and play a Youtube video of the song on an hour loop while sitting and watching you guys being cute and wishing they had someone to do this kind of stuff with, well most of them. When you both realize this you're very embarrassed and Iida's just like 'I...I'm taking (Y/N) home now..." flustered as hell, he leads you back to your house. At your stoop he pulls out this case out of his pocket, obviously nervous, and inside is a beautiful necklace that the got you. He knows how you feel about expensive gifts but felt that if he didn't get this for you it wouldn't be a Valentine's Day well celebrated. After he helps you put on the necklace, you tell him to wait as you go inside and get him his gift. Since Iida does enjoy Star Wars you got him a death star waffle maker, which he brings to the dorms and eventually makes an art out of it. Everyone's super impressed with Iida's death star pancakes and several ask you where you found the waffle maker because they need one for reasons. Though you don't tell them because and you quote 'the best part of a quest is figuring out how to get there' so Iida remains the Waffle Lord for quite awhile.