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Dating the Slytherin boys (+ Harry) ▪ HEADCANONS

Requested: No

Characters: Mattheo Riddle, Tom Riddle, Theodore Nott, Draco Malfoy, Blaise Zabini, Regulus Black, Harry Potter (+ y/n)

Warnings: NSFW mentions, English is not my first language

A/N: I'm not sure I like this but here we go. However I have to say I like Regulus' one so I might turn his version into a one shot one day (when uni won't be killing me slowly). This will include also the pre-dating/flirting stage as well. SORRY FOR THE TYPOS. Comments and feedback are always appreciated. Enjoy! ^^

Tag list: @helendeath @im-jesus

Tag list for this story: @anawritez-posts @pumpkinchee @alwayslatetothefandoms

Mattheo Riddle:

His feelings for you probably confused him at first

If he falls first, he either won’t let you know or will do everything to get your attention (‘Hey, y/n, come sit here, the seat is free!”, “y/n, do you mind helping me with the homework for Snape? I can’t bloody do it”, “How about we go to Hogsmeade, just you and me?”, “you look beautiful, y/n”)

Your love for him always calms him when he gets anxious or when he’s upset, especially after his father comes back

Will tell you things he never told anyone

Would rather spend time with you than with his friends

Is terrified something will happen to you because of his father

VERY jealous, but trusts you

Despite easily getting angry, he can’t get mad at you. Even during arguments

LOVES sleeping in your arms or when you just hold him

He's crazy about your body

Loves showering with you, and we both know how it often ends

HOT, passionate sex

Will randomly eat you out without expecting anything in return (doesn't mind if you return the favor, though)

100% calls you "baby" or "love" all the time

Doesn’t care about what anyone thinks of him as long as you love him

Your love makes him feel lighter and stronger

You're his whole world

Feels bad when he hears someone criticize you for dating him

Always makes sure you don’t overwork yourself, and makes sure you get enough sleep, water and food, and comforts you when you're anxious

Holds your hands when he's anxious or stressed

Will listen to anything you have to say

Crazy about your perfume

Theodore Nott:

Struggles to express his love or feelings in general, at least in the beginning

Has never done serious relationships before, and it may cause some trouble in your relationship, as you end up believing he doesn’t care about you

It causes many fights, and the last one will be the first time he says ‘I love you’

Always goes to you for comfort

Loves sleeping with you in his arms, or cuddling, and with time he can’t sleep without you

Loves watching you sleep

Loves having you on his lap

Always gets you great gifts (even randomly)

“Well, it thought it was pretty, and…it reminded me of you.”

Will fight any guy who is rude to you or acts like a creep

Very jealous (trusts you, doesn’t trust others)

Doesn’t mind PDA at all, will gladly hold your hand or kiss you in public

Always has a hand on your waist or his arm around your shoulders

Very supportive in everything you do, even when he doesn’t understand it/isn’t really interested in it

Isn’t very good with comforting people (mostly because he's not used to it), but will hold you and listen to you as long as you need, can even give you advice/reassurance

Every compliment/'I love you' you say melts his heart and means much more to him than he shows, same goes for anything you do for him

Loves doing fun things, even if it’s just throwing snowballs at each other during winter (which ends in loving kisses, just savouring the joy of being together)

Love getting in a pool with you and playing "childish" games during summer

Any form of intimacy means A LOT to him

He's used to hooks up and "fucking" but it takes him a bit of time to have sex with you (despite being crazy about you and your body) because you mean everything to him and with you it's really making love instead of just "fucking"

The first time is loving and slow yet passionnate (eye contact at all times, hands holding, desperate kisses from him), and it gets a bit rougher and passionate the next times (but aftercare, which he isn't used to, is always on point and keeps getting better)

Is secretly very insecure, and is terrified you will leave him (especially for another “better” guy)

Craves your touch and your love but won’t admit it

His boggart is probably you being dead alongside his mother

Will tell you sweets things in Italian

Very clingy in private - and also in public with time

With you he learns to be happier and discovers a happier side of himself he didn't know he had

Loves you much more than he actually shows at first

Will often say you're all he has (and means it)

But with time, you have no reason to doubt his love and he’s the perfect boyfriend

Blaise Zabini:

Probably will court you like the gentleman he is

He doesn’t trust people easily and might be a little distant (while always polite and kind) in the early stages of your relationship

But with time he becomes very warm and smiles a lot

Always kisses the top of your hand or your forehead

Doesn’t do much PDA except for holding hands and kisses on your forehead

However in private he’ll 100% cuddle you and hold you

Dates in parks or restaurants

Get you flowers at least once a month

Will always defend you against others

One of his love languages is acts of service

Lorenzo Berkshire:

You either were friends before dating or he fell in love with you at first sight, there is no in between

Takes you on fun dates (arcade, funfair, theme parks)

Can be shy at the beginning, which will make it a bit hard for him to talk about how he feels about you

Movie nights where you two eats lots of snacks and sweets while cuddling

Always smiles when you enter a room

So supportive

Loves when you're on his lap

He has no problem with PDA

Quickly willing to meet your family if you agree

He’s a great listener and mostly gives good advices

Loves taking naps with you

Always makes you sure you get enough sleep, water and food

Won’t let you get yourself into dangerous situations

Loves to go anywhere with you, no matter the activity and even if he just follows you around

Many pet names

If you're Muggleborn or grew up among Muggles, he will totally ask you questions about the muggle world

Passionnate sex, will get rough if he hasn't seen you in a long time or if it's angry sex after he got jealous

His aftercare is the best, and he's always thankful you trust him enough to have that form of intimacy with him

Draco Malfoy:

Won’t flirt at first with you but keeps wanting your attention

Tries to seduce you with expensive gifts, and is a bit taken aback when you say it doesn’t work

Continues to get you gifts, but will make sure they match your interests/tastes, and keeps expensive gifts for your birthdays and Christmas (even though he’d like to get them all year for you)

At first he doesn't show any weakness in your presence

With you he’ll learn patience and to focus of more positive things, and also to stand up to his father

Takes you on dates every chance he gets

Will ditch his friends to spend time with you

Probably makes Crabbe and Goyle carry your bags or do things for you

So proud to be dating you, it might even make him more arrogant

Gets grumpy when jealous but after a kiss on the cheek he’s back to his normal self

Will invite you to his home and write you nearly every day during holidays

Hates it when Harry or any Gryffindor boy tries to talk to you

Surprisingly has no problem with PDA

Loves when you come to see him play during Quidditch matches

Tom Riddle:

Oh boy

It started with him admiring/watching you from afar, for a reason he can’t understand

SUPER confused by what he feels for you and why

Will probably try to get closer to you through homework or through books if he sees you read one

Will know everything about you, and will secretly follow you, saving you if you’re in danger with you never knowing who saved you

Crazy about your perfume, so much so that it makes him steal one of your clothes just to be able to smell it anytime he wants

After a while, he’ll spend most of his time with you without ever admitting he likes it

Will probably let you know his feelings for you after he cast a spell on a guy for being a creep with you

Won’t let another man touch you

Will ask Mattheo for advice to be better or to make you fall in love with him

Will do your homework without hesitation, even if he pretends that he hates it, and will leave explanations so you understand his answers/his work

No PDA except for holding hands or your hand under his arm, but will make sure to stay close to you at all times

Is a surprisingly good listener

VERY jealous, but surprisingly isn’t mad or suspicious at you

“Did you enjoy having his attention? Do you wish for me to show you how my attention is better?”

He doesn't stress over homework or stuff like that, so he finds it ridiculous when you do (learns with time to be more understanding)

Will let flowers in your room with a note on it

Pretends to not care about the gifts you get him for his birthday or Christmas but it actually means so much to him as no one ever got him any gifts before

Nothing the others say about him gets to him, but he gets angry when he hears someone say that you deserve better than him

As book!Tom who grew up in an orphanage: he's secretly insecure about his background and the fact that he’s poor, and thinks you deserve better

As Voldemort: Might be torn between continuing his goals for power or spending a simple life with you; is aware you’ll leave him if he gets on a darker path

As Voldemort’s son: would do everything to protect you from his father, and if he’s forced to get the Dark Mark, he will makes sure you don’t know

Possessive kisses

Would hurt anyone who does you wrong

Borrows money from Draco to take you on dates or to get you gifts, as he feels like you deserve the nicest things, even though you keep telling him his mere presence is enough

May feel a little bit guilty that he can’t properly show you his love like “normal” boyfriends do

Won’t admit it but considers you the only good thing in his life, and if he ever lost you he’d get on a dark path

Won’t cuddle at first, but if you wake up first you’ll find him sleeping close to you, with at least one of his hands touching you

Always notices when you don’t eat, sleep or drink enough

You’re the first (and only) person he will feel romantic love for

He has a bit of sexual experience before, but with you it's completely different - once you guys have sex for the first time, he becomes obsessed with your body and how it makes him feel

Loves fingering you

"You like it, dove?"

Even if you guys don’t work out, he won’t ever be with somebody else

Would ask your parents for you hand in marriage, but honestly it's just out of politeness, the only answer that matters to him is yours

Regulus Black:

Like Blaise, he was raised the old fashioned way

Acts coldly towards everyone except you, his tone and eyes gets warmer and kinder when talking/looking at you, and you’re the only person he’ll smile at

You were his best (and only) friend and he has been in love with you for years

He hides his feelings very well, but one day you start dating someone else (thinking Regulus doesn’t share your feelings) but he can’t bear it and confesses his feelings

Always defends you

He’ll take you on restaurants or picnics dates, always bringing flowers

Mostly fine with PDA (holding hands, hands on your waist)

Thinks he’s very lucky to have you

Probably already starts thinking of marrying you during your last year at Hogwarts

A bit jealous, but can’t stand it when Sirius tries to talk to you

Will gladly do your homework with/for you

Loves it when you sleep in each other’s arms, loves feeling you close

Loves it when you call him “Reggie” (only you is allowed to)

Will literally do everything you ask him to

You’re everything to him

Can’t stay away from you for long

Will get worried if you’re five minutes late

Always calls you “sweetheart” or “love”/”my love”

Slow, romantic sex most of the time but sometimes he needs to be rougher

Thanks to you he’ll feel lighter and he will become kinder

You’ll even make him change his views on blood purity and stand up to his parents, and with time he gets closer to Sirius thanks to that (and you)

If that doesn’t change and he still joins Voldemort, he’ll leave you a letter before going to the cavern, saying how much he loves you and how much you mean to him

Harry Potter:

Don’t expect any pet names from him, but he might create a nickname with your name (like he calls Ginny ‘Gin’ in the Cursed Child)

His love languages are fierce protectiveness, loyalty and a patience he didn’t knew he had

Has no problem with PDA because he doesn’t care about what other people think

Loves cuddles

Rarely gets mad at you, and feels guilty when he does

Mostly gets mad at you when you hurt yourself (for example during Quidditch) but it's also because he was scared for you

Hot kisses in private

Will be jealous if he sees you with another guy

He’s passionate in a lot of things he does, and it includes you and everything you do

Will fiercely defend you again anyone, can even throw hands

Gets FURIOUS when Umbridge hurts you during detention, and will cuddle you for hours and do everything he can to make the pain disappear

Knows people are mean to you during fifth year because you're dating him and he hates it

During that year the only peace he feels is when he's holding you or when you sleep in his arms (it's also the only time he doesn't get nightmares)

Very supportive

Loves getting you gifts

You make him feel SO happy, he’ll just keep smiling for no reason

Gets more and more clingy with time

Always write to you during the holidays (you always invite him to come to your house)

I'm not sure about sex while you guys are at Hogwarts but he 100% feels lust for you, there will definitely be hot making sessions when you guys are alone in a dark corner of the castle and it often ends up with you against the wall with your legs around his waist while he kisses your neck and caresses your legs

However sometimes he just can't stop himself and will eat you out (even maybe finger you at the same time), and will be proud when you come

Any act of service you do for him means a lot

You're always worried about him when he's at the Dursleys but he reassures you that he's fine

Comes to you in the middle of the night if he has a nightmare and generally comes to you for comfort or to rant

Needs you more than ever after Voldemort comes back and after Sirius’ death

Misses you like crazy during his quest for Horcruxes, and he can’t bear the thought of something happening to you

Might struggle to show it, but he knows and is thankful of how patient and comprehensive you are with him, and that makes him want to be the best boyfriend he can be

Terrified Voldemort might hurt/kill you

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