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4rainynite · 4 months ago

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EAH Dorm Headcanons pt 29

Here are my headcanons of everyone's roommate from freshmen to senior year of Ever After High (yes, I know it's called something else in the series).

Raven

Freshmen -During Freedom Year Raven didn't have a roommate because it was the year after the Evil Queen went off script and to prevent a student from calling their parents that they were rooming with the future evil queen and cause Raven harm they decided it was best that Raven didn't have a roommate her first year. Even though Raven understood why she didn't have a roommate this made her feel isolated, until she befriended Maddie & Cedar.

Sophomore - Raven and Maddie were supposed to be roommates Legacy Year before Apple changed the rooming assignments without eithers permission. Maddie was the first friend Raven meet and were super supportive of each other so it's obvious they would be good roommates!

In Apple's misguided way to bond with Raven (and the Headmaster tricking her) requested to room in with her. At first the two were respectful of each other despite their differences even before the Royal & Rebel debate. Over time the two do form a friendship, but still find ways to annoy each other because come on they're roommates.

Junior - Maddie and Raven finally become roommates! They're already best friends and enjoy each other company. Every day is an endless band session and tea party!

Senior - Potential roommates for Raven are Cerise, Ginger, Cedar, Cupid, and Darling.

1.Cerise - Raven was the first-person Cerise opened up to about her family secret and never revealed it to anyone. Both girls support each other and are pretty quiet individuals.

2. Cedar - Cedar and Raven both express themselves through the arts and are very truthful. Both girls support each other and are there for the other in times of need.

3. Ginger - Ginger and Raven both had evil destinies and mommy issues (though Ginger and her mother's relationship is more supportive now). Raven helped Ginger prove she only wanted to make sweets for others to enjoy and not fatten them up proving a great support system.

4. I honestly think it would be funny if those two would be roommates. At first, it's awkward because Cupid had a crush on Dexter and Dexter is now Raven's boyfriend. But honestly, they hung out before that and have a talk and realize their still friends even with Dexter in the picture. Both go to each other on different advice and bond over gothic fashions.

5. Darling - Both girls are rebellious, support each other, and just want to be their true selves. Also, it gives them time to bond more since their future in-laws.

Apple -

Freshmen - Ashlynn and Apple would bond over their future destinies, upholding family traditions, and fashion. While Apple voiced her excitement, Ashlynn was beginning to have doubts, but decided to accept it...until Hunter came around.

Sophomore - Briar was supposed to be Apple's roommate until Apple requested to be Raven's roommate to bond with her future villain and make sure Raven would go down the wrong path. Over the course of the series Apple learns to see Raven as an actual friend instead of just a steppingstone in her story.

Junior -Briar and Apple are already best friends so rooming together is no problem. But, after Legacy year they realize how much they don't know about the other and talk things over to strengthen their friendships.

Senior - Potential roommates for Apple are Blondie, Holly, Duchess. The reason Darling isn't on the list is because Apple and her started dating during Sophomore year.

Blondie- Blondie and Apple are already friends and we know they are on countless platforms would exchange beauty and social media tips. This will also be an opportunity for the two to do exclusive interviews.

2. Holly- Apple and Holly are both studious students and would have countless study sessions and Holly would ask Apple's opinions on her stories and in return Holly would boost Apple's confidence in her hair.

3. Duchess- It's a double-sided karma for the two to be roommates. Apple singing and eternal cheerfulness would drive Duchess crazy, while Duchess snooping into her belongings and Pirouette's honking would drive Apple crazy. Long story short they do not get along.

Maddie -

Freshman -I think Cedar and Maddie became friends after being roommates during freshman year. Both girls were new to the whole living away from home. Maddie is the reason Cedar and Raven became friends.

Sophomore - Raven was supposed to be Maddie's roommate before the headmaster made her switch with Kitty. Kitty and Maddie already get along and not just because they're Wonderlanders. They enjoy each other's company and understand the other.

Junior - Raven and Maddie finally become roommates during junior year! Maddie always knows how to make Raven smile and Raven enjoys spending time with Maddie.

Senior - Potential roommates for Maddie are Lizzie, Bunny, Ginger, and Cerise.

Lizzie - Both Lizzie and Maddie care and respect each other, and after a long day of shouting Maddie would supply Lizzie tea.

2. Bunny - Despite Bunny being calm and Maddie being mad both girls get along and are very messy.

3. Cerise-Maddie accepted that Cerise was half wolf and was one of her first friends. Cerise appreciates all Maddie has done to make her feel welcomed even before the big reveal.

4. Ginger - Both Maddie and Ginger have a sweet tooth I can see Maddie supplying the tea and Ginger supplying the sweets. I also believe Ginger works part time at the Mad Hatter's Haberdashery and Tea Shoppe making the two co-workers and roommates.

Briar

Freshman -Briar would've been Blondie's first interaction with royalty and Blondie couldn't believe she was with the top three popular princesses in the school. Those two are usual up to date with the latest gossip due to Briar hearing everything in her sleep and Blondie's reporter skills.

Sophomore -Apple was supposed to be Briar's roommate before the switch. Now, Briar is Ashlynn's roommate the two bond over fashion and questioning their destines.

Junior - Apple and Briar finally become roommates but have to reconnect after realizing they may not want to follow their pre-written destinies.

Senior - Potential roommates for Briar are Lizzie, Cupid, Rosabella, Bunny.

1.Lizzie - Briar was the one who told Lizzie she didn't have to do everything like her mother did making Lizzie want to be a kinder queen. The two would bond over fashion and Briar would help Lizzie understand Ever After and Lizzie would introduce Briar to Wonderland culture.

2.Cupid - Cupid went to Briar to help plan the True Hearts Day party and they make 2/3 of the Pink Squad of course they'd be roomies. Both give each other advice on matters of the heart.

3.Rosabella - Due to Briar's dad being a jerk to Rosabella's dad just because he was a beast, the two haven't seen each other since they were kids. Being roommates at Ever After High would give them time to reconnect after years of being apart. Briar does host parties for Rosabella's causes and help teach Rosabella to relax.

4.Bunny - Both are in many after school clubs mainly the party planning committee. With Bunny's time management skills and Briar's ideas they throw amazing parties together and hang out together.

Cedar

Freshman - Maddie was Cedar's first roommate and both girls were new to the whole living away from home. Maddie made Cedar feel right at home despite not knowing Riddlish or Wonderland custom.

Sophomore - Cedar and Cerise got along, but because of Cerise's secret they were pretty distant. Over time the two bonded over art and sports until Cerise revealed her secret to Cedar.

Junior -Cedar and Lizzie are both artistic girls and would collaborate together to create different outfits and paintings and draw inspiration from each other.

Senior - Potential roommates for Cedar are Kitty, Ashlynn, Cupid, Raven, and Lizzie.

1.Kitty - I know y'all might think it's strange that Kitty would be Cedar's roommate, but Kitty does consider Cedar as an almost friend. Kitty would defend Cedar from those who tried to use her curse against her.

2.Ashlynn - Ashlynn trust Cedar since she kept quiet about her and Hunter dating before they came out, Cedar knows Ashlynn would never use her curse against her. Both girls care for nature and are artistic with Cedar's paintings and Ashlynn's dressmaking.

3.Cupid - Cedar and Cupid both believe the truth will set you free and would provide each other with great advice.

4.Raven - Cedar and Raven support each other both in their beliefs and in their artwork.

5. Cedar and Lizzie are both skilled in fashion, have a creative streak, and hangout a lot.

Blondie

Freshmen- Blondie was Briar's roommate during freshmen year. Seeing how both girls love to gossip and be in the know they were a perfect match.

Sophomore - At first Blondie had the whole dorm to herself and as much as she loved to brag about it, she did get lonely. Cupid arrived a month or two and was paired with Blondie and the two formed an amazing friendship as both go to each other for comfort and advice. They also appear on each other's shows from time to time.

Junior - Blondie and Ashlynn were already the core Royals and a lot hangout so why wouldn't they be roommates. I can see Ashlynn being annoyed that Blondie keeps borrowing her shoes.

Senior - Potential roommates for Blondie are Apple, Duchess, Holly, Poppy, Ginger.

1.Apple- We can all agree that Blondie would lose her mind if she found out she was rooming with Apple. Both like to keep appearances and would give each other beauty tips and Apple would guest star on Blondie's show.

2. Duchess - Both girls love to gossip, but Duchess does it out of spite and jealousy while Blondie is naturally curious and will take others' feelings into consideration. Both girls would bond over jealousy for their fellow Royals with happily ever afters.

3. Holly- Both girls would get along due to how both care about their hair and enjoying learning/gathering info. Holly would go to Blondie for creative criticism for her stories and Blondie would have Holly over for interviews and new ideas to make her webseries interesting.

4. Poppy- Blondie would love having Poppy as a roommate to do her hair and Poppy would love Blondie to let her experiment new hairstyles. Besides Blondie is a regular at Poppy's hair salon so that's a no brainer.

5. Ginger- Both girls bonded over their webseries. Ginger would have Blondie taste test her sweets and guest star on her show, and Blondie would do interviews with Ginger.

Kitty

Freshman - After evacuating from Wonderland to escape the Evil Queen's curse, Lizzie and Kitty were made roommates to keep the Wonderlanders together. Kitty and Lizzie already are besties so being roommates was no problem.

Sophomore - Maddie became Kitty's roommate after Apple's switcheroo. Maddie and Kitty were already friends and both girls enjoy pranks and each other's company. I believe Ashlynn was originally Kitty's roommate and the two did not get along. Ashlynn was too goody-goody for Kitty and Kitty's pranks and trying to eat the birds and mice would upset Ashlynn. Apple's misguided attempt to bond with Raven ended up benefitting Ashlynn and Kitty.

Junior - Bunny and Kitty are pretty polar opposites, but after having Faybelle as a roommate Bunny was relieved to have a familiar face as a roommate. Kitty still teases Bunny over her crush on Alistair, but it comes back to bit her when Bunny won't stop talking about him.

Senior - Potential roommates for Kitty are Cedar, Courtly, and Bunny.

1.Cedar- Kitty considers Cedar as an almost friend and now that Kitty knows how pranks can hurt people, she keeps the questions basic as possible. Ican see the two knitting as a binding experience.

2. Both Courtly and Kitty enjoy pranking their classmates and are huge class clowns. No one is safe from them!

Ashlynn

Freshman - Apple was Ashlynn's roommate during freshmen year, being the top three fairy tale characters it was obvious they would room together and bonded over making their mothers proud.

Sophomore - Briar became Ashlynn's roommate after Apple switched to became Raven's roommate. The two were already friends and bonded over fashion over time they bonded over wanting to change their stories. Kitty was originally Ashlynn's roommate and the two did not get along due to how messy Kitty was and Ashlynn liked to keep things tidy, and Kitty would purposely rearrange Ashlynn's shoe collection. Apple ended up doing those two a favor.

Junior - Blondie would be excited to room with Ashlynn not just because she's a fellow royal/royalty, but because they are friends. Blondie would have Ashlynn and Hunter on her show as guest a lot.

Senior - Potential roommates for Ashlynn are Cupid, Holly, Poppy

Cupid- Ashlynn was there for Cupid when she was falling out of love with Dexter and Cupid would support Ashlynn's relationship with Hunter. Cupid would sometimes ask Ashlynn and Hunter to be on her show to help others going through the same thing they were going through.

2.Holly- The two regularly hangout and enjoy nature so why not? Holly would go to Ashlynn for inspiration for her stories and Ashlynn would open doors for Holly and help with advertising for The Glass Slipper.

3.Poppy- Ashlynn is a regular to Poppy's salon and the two regulary hangout. Poppy would go to Ashlynn for advice for choosing her destiny.

Cerise

Freshman - I think it would be interesting if Ramona was Cerise's roommate during freshman year. In my world the two are cousins and didn't know they were related until freedom year. How the two interacted is how Apple wished Raven would act with her (let's be real we'd all rather die than have an evil roommate just look at poor Bunny). Ramona would ruthlessly antagonize Cerise until one day Ceise bite back and Ramona was blamed for it which is why she went to reform school until it was time for Legacy Day.

Sophomore - At first Cerise was nervous to room with Cedar due to her truth curse. Over time the two became friends and Cerise trusted Cedar with her secret. The two bond over sports, art, and how they love their families.

Junior - Ginger and Cerise knew each other already since they grew up in the Dark Forest. After, Cerise's reveal the two bonded more and rekindled their friendship. Cerise always lends a helping hand when Ginger needs an assistant.

Senior - Potential roommates for Cerise are Raven, Maddie, Darling.

Raven - Raven was the first-person Cerise revealed she was half-wolf too and kept it secret. Both supported each other during the rebel movement so they'd make good roommates.

2. Maddie - Maddie was the second person to know about Cerise's secret and was always supportive of her friends. Cerise also loves Maddie's fun personality.

3. Darling - Cerise and Darling hung out a lot during 'Dragon Games' and both girls were very secretive. They would so support each other and be amazing roommates.

Duchess

Freshman - Had a roommate or had the room to herself. It wouldn't matter if she had another princess as a roommate or a non - princess, they wouldn't have bonded. If she had the whole dorm to herself, she would brag about it to the others.

Sophomore - At first Lizzie and Duchess didn't get along due to culture classes, Lizzie being messy, and both having a thing for Daring. After 'Next Top Villian' the two bonded over wanting to uphold tradition and their villainous classes. Lizzie was Duchess's first friend.

Junior - Faybelle and Duchess are besties due to being the school's mean girls and being competitive.

Senior - Potential roommates for Duchess are Apple, Courtly, Jackie, Justine.

1.Apple being Duchess's roommate would be karma for her all the times she was mean to her and others. With Apple's perky personality and singing all the time Duchess would be running to Raven questioning how she survived freedom year with her?

2.Courtly - During 'What's In The Cards for Courtly Jester' Courtly did say Duchess was her friend and the two hangout. They would bond over wanting a better destiny and being respected.

3. Jackie - I can see Jackie and Duchess butting heads, but at the same time bonding over how the system is rigged to benefit others. Jackie would complain about how people like Crystal who didn't know how to tie her shoes before are in charge and Duchess would complain how some like Apple, Briar, and Ashlynn get to break rules and never get in trouble for it and still get happily ever afters.

4. Justine - Duchess and Justine have a friendly rivalry and respects the others dedication to dance.

Darling

Freshman - I can see Darling having a dorm to herself as her parents request due to her destiny of being alone only to be rescued. That benefitted Darling as she was free to exercise, practice sword fighting, and read up about Wonderland.

Sophomore - Rosabella and Darling got along very well and became bffs. Both girls supported each other and their desire for justice and equality, though Rosabella was straight forward while Darling worked behind the scenes.

Junior - Bunny would be a great roommate for Darling since both girls are quiet and Bunny would tell Darling all about Wonderland.

Senior - Potential roommates for Darling Cerise, Raven, Ginger.

1.Cerise - Cerise and Darling hung out a lot during 'Dragon Games' and both girls were very secretive. Cerise supported Darling's desire to be a knight and Darling supported Cerise being half wolf.

2.Raven - Both girls are rebels and support each other, plus they're future in-laws and bond very well.

3.Ginger- Darling helped Ginger in 'Spring Unsprung'. Darling would accompany Ginger when gathering ingredients for her sweets and Ginger would have Darling guest star on her show.

Cupid

Freshman - Didn't attend Ever After High School since she was at Monster High.

Sophomore - When, Cupid transferred to Ever After High she was assigned Blondie as a roommate. The two bonded over having webseries and would become close friends.

Junior - Ashlynn invited Cupid to the Blue Moon Forest Festival during the 'Through the Woods' arc when Cupid was trying to get over Dexter. Ashlynn and Cupid care for each other and use the balcony to plant Cupid's roses.

Senior - Potential roommates for Cupid are Poppy, Holly, Cedar, Briar.

1.Poppy or Holly - They would both hangout with Cupid so I can she her being roommates with either one.

2. Cedar - Being a radio host that offers love advice sometimes Cupid may need advice and go to Cedar for it. Seeing how Cupid's family is made up of Greek gods Cedar goes to her for art advice.

3. Briar - Both Cupid and Briar make 2/3rds of the pink squad so of course they'd make amazing roommates.

Holly

Freshman - Anybody really and no she didn't have the dorm to herself because doors lock behind her.

Sophomore - Her sister, Poppy, became her roommate after finding a loophole in the rules. During that time they found out that Poppy was the one who was supposed to inherit the Rapunzel role, but kept it a secret and remained close.

Junior - Justine since both are artistic in writing and coming up with new ideas.

Senior - Potential roommates for Holly are Blondie and Ashlynn.

1.Blondie - Holly would go to Blondie for advice for her stories and unlock doors for her. Blondie would have Holly over for interviews and new ideas to make her webseries interesting.

2. Ashlynn- Ashlynn and Holly both have trouble with their curses, so Holly reminds her of the time and Ashlynn unlocks doors for Holly.

3. Bunny - Due to Holly being curious she might ask Bunny things about Wonderland culture and since Bunny is always on time Bunny can open doors or rabbit holes for Holly.

Poppy

Freshman - No one. She didn't attend Ever After High School until Freedom year.

Sophomore - Holly found a way so Poppy could attend Ever After High School. During that time Poppy found out she was supposed to be the next Rapunzel, but was happy to discover herself and let Holly have it.

Junior - Farrah would be a nice roommate for Poppy since both girls are artistic and enjoy fashion.

Senior - Potential roommates for Poppy are Ashlynn or Blondie.

Blondie is already a regular at Poppy's salon and would be a model for Poppy's new hair styles.

Poppy would regularly go to Ashlynn for destiny advice and is also a regular of Poppy's salon.

Lizzie

Freshman - Kitty and Lizzie were made roommates after they evacuated Wonderland and to keep the Wonderlanders together. Seeing how they were already bffs it's a no brainer that they're roommates.

Sophomore - Duchess and Lizzie became friends after getting difficulties between them cleared up. Both want to make their mothers proud and uphold tradition.

Junior - Bunny was already another close friend to Lizzie, plus Bunny needed a break after being roommates with Faybelle.

Senior - Potential roommates for Lizzie are Maddie, Briar, and Cedar.

Maddie - Fellow Wonderlander, speaks Riddlish, and endless tea parties to sooth your throat after endless shout, Maddie is the perfect roommate.

2. Briar- Briar helped Lizzie realize that she didn't have to do everything her mother expects her to be and that she can be a kinder queen, plus both girls are fashionistas and collab on different outfits.

3. Cedar - Lizzie helped Cedar during an art project and the two do hangout regularly. So I think they would be a good match as roommates.

Rosabella

Freshman -Nina and Rosabella would bond over protecting wildlife and nature.

Sophomore - Darling and Rosabelle became friends instantly, bond over justice, and are supportive of each other.

Junior - I can see these two getting along since both like nature and Rosabella would help Jillian with her protest to let girls take heroic classes and boys take princessology classes.

Senior - Potential roommates for Rosabella are Ashlynn or Briar.

Ashlynn- Ashlynn is a fellow nature and animal lover and her ability to talk to both would benefit Rosabella.

2. Briar - The two have been separated for years due to Briar's father prejudice against beast. Rosabella knows that Briar is not at fault and the two bond over lost time.

Faybelle

Freshman - Ginger and Faybelle used to be friends when they were kids, but when their mothers got competitive so did Faybelle. Faybelle would use Ginger to do her homework and remind her of their villionious destinies. In some twisted way she still sees herself as Ginger's friend while Ginger begs to differ.

Sophomore - Faybelle had the whole dorm to herself and liked it that way! After, Alistair and Bunny arrived Bunny was made Faybelle's roommate. I honestly think Headmaster Grimm did that on purpose since he knew of Faybelle's temper. Bunny and Faybelle were one of the few roommates that did not get along!

Junior - Duchess was someone Faybelle gets along with well. They both love to antagonize those who are goody two shoes or those who don't follow their destines.

Senior - Potential roommates for Faybelle are Jackie, Ramona, or Farrah.

Jackie - I can see Jackie and Faybelle butting heads, since both are leaders the two would not get along.

2. Ramona - Ramona would take none of Faybelle's nonsense and the two would try to stay as far away from one another. And the rare occasion Faybelle would test Ramona's patience she'd regret it!

3. Farrah - Karma has finally struck Faybelle since she's no longer viewed as a threat by her classmates and is now co-captain of the cheer squad with Farrah. Don't worry about Farrah she can handle Faybelle now.

Ginger

Freshman - Faybelle and Ginger used to be friends until Faybelle became her bully. Having Faybelle as a roommate did nothing to help Ginger's self-esteem.

Sophomore - Melody was breath of fresh air after having Faybelle as a roommate. Melody respected Ginger and enjoyed her sweets. Melody would ask Ginger to cater her gigs and invite her to her shows.

Junior - Cerise and Ginger grew up together in the Dark Forest as they got older Cerise became distant. After the reveal Ginger welcomed Cerise with open arms and was glad to have her friend back!

Senior - Potential roommates for Ginger are Darling Maddie Raven

Darling- The two bonded after 'Spring Unsprung' and Darling enjoys Ginger's treats.

Maddie- Ginger works part time at Maddie's dad's shop so they bond during work and have endless tea parties.

Raven- Raven supported Ginger from the beginning and both have mother issues (mainly Raven), the two bond over past experiences and what the future holds for them now.

Bunny

Freshman - No one. She didn't attend Ever After High School until Freedom year.

Sophomore - First she lost her home, moved to a new world,and had Faybelle as a roommate cut Bunny some slack! Bunny was another victim of Faybelle since she would threaten the poor Wonderlander. During the last months of school Bunny grew a backbone, told Faybelle off, and got a dorm to herself.

Junior - Bunny and Kitty are good friends despite their personalities clashing, but after having Faybelle as a roommate Bunny was relieved to have a familiar face as a roommate.

Senior - Potential roommates for Bunny are Maddie, Lizzie, and Briar.

Maddie - Maddie and Bunny are good friends both messy and have a time motif tied to them. Bunny is definitely the calmer of the two which makes a good opposites attract roommate situation.

Lizzie -Bunny was overjoyed to have as a roommate Lizzie! The girls were already friends and bond over Wonderland and the new experiences at Ever After High School.

Briar- Both are in a ton of clubs together so making them roommates gives them time to come up with more club ideas. Briar would also help Bunny relax and make Faybelle apologize for how she mistreated Bunny.

Justine

Freshman - Farrah and Justine instantly bonded as roommates and have been friends ever since. They also help each other out during different projects.

Sophomore - Justine had the whole dorm to herself which she would use to practice her dancing even though she felt lonely sometimes wishing for a roommate. Then, Ramona came back from reform school making Justine regret her wish. After, 'Moonlight Mystery' the two became friends.

Junior - Justine and Meashell would be friends due to Farrah and Justine would ask Meashell to audition for some of her plays.

Senior - Potential roommates for Justine are Duchess and Melody.

Duchess -Justine and Duchess have a friendly rivalry do pairing them as roommates would be interesting.

2. Melody - Melody would play music for Justine to dance to both in private and for her musicals/plays and Justine would teach Melody new dance moves.

Ramona

Freshman - Cerise and Ramona were made roommates due to their destiny. at the time Ramona didn't know they were cousins. Ramona did something that caused Cerise to snap and send her to reform school for the rest of freshmen year.

Sophomore - After, returning from reform school Justine became Ramona's roommate. The two didn't get along at first but became friends later.

Junior -Jackie would be Ramona's roommate junior year, I don't know why but I feel like they would get along. Maybe because those two have a thing against authority.

Senior - Potential roommates for Ramona are Rosabella.

Rosabella would get Ramona on board for justice for beast, animals, and were people and at the same time the two would butt heads.

Farrah

Freshman - Justine and Farrah's friendship started when they were assigned roommates. Justine and Farrah would also help each other during certain projects.

Sophomore - Farrah had the dorm to herself, but after having a great roommate like Justine she got lonely. Luckily, Meeshell arrived and the two clicked instantly as Farrah showed Meeshell the ropes.

Junior - Nina and Farrah get along quite well and Nina would help find materials for Farrah's clothes to design.

Senior - The only reason Faybelle would be Farrah's roommate during senior year is because Farrah gained a backbone and Faybelle has been knocked down a couple of pegs, Farrah and Faybelle are now co-captains on the cheer squad. Having Farrah as a roommate is karma for Faybelle.

Melody

Freshman - Anyone really, Melody seems like a cool roommate or she had the dorm to herself.

Sophomore - Melody sympathized with Ginger and was her first friend. Also, Melody enjoys Ginger's sweets and would invite Ginger to her shows.

Junior - Jillian and Melody would be roommates due to their adventurous streak, and each enjoys the others shows.

Senior - Justine would be Melody's roommate and the two would collab about music and dancing.

Meeshell

Freshman - No one. She didn't attend Ever After High School until Freedom year.

Sophomore - Meeshell didn't want a room to herself, so Farrah was assigned her roommate. Farrah helped Meeshell breakout of her shell and get comfortable with the school.

Junior - Justine and Meeshell would hang out with Farrah so being roommates would be good for them.

Senior - Bunny might be a good roommate for Meeshell since both are shy and still discovering Ever After high.

Nina

Freshman - Nina and Rosabella would bond over protecting wildlife and nature.

Sophomore - Jillian and Nina both care about nature and sometimes go on adventures together.

Junior - Farrah and Nina would get along and Nina would help Farrah find inspiration in nature for her fashion designs.

Senior - Ashlynn might be a good fit for Nina since they both care about the environment and love animals.

Jillian

Freshman - I can see Jillian having the dorm to herself to practice her tricks.

Sophomore - Nina and Jillian are both nature lovers and go on adventures together.

Junior - Melody both have an adventurous streak and Jillian uses some of Melody's music in her videos.

Senior - Briar and Jillian are both thrill seekers and would do daredevil activities together.

Daring

Freshman - Dexter and Daring would be roommates due to being from The Main Charming family and siblings normally room together. Daring sees it as a bonding activity to be close to his little bro.

Sophomore - Hopper and Daring get along great as roommates and friends! Both are good at wooing (in frog form for Hopper anyway) and are seen hanging out.

Junior - Hunter and Daring both have a different version of a strong man for Hunter it's rugged and Daring it's civil/gentleman. Both get along and I can see them having contest on who's the toughest.

Senior - Potential roommates for Daring are Alistair or Chase.

Daring saw Alistair as heroic for bring the Storybook of Lgends back and protect his friends from the Evil Queens curse. I can see Daring admiring Alistair despite Alistair not seeing himself as a hero.

2. Chase and Daring would be spare buddies and workout a lot.

Hopper

Freshman - Humphery and Hopper bonded over their love of tech and video games.

Sophomore - Hopper couldn't believe Daring Charming was going to be his roommate! Hopper and Daring are close friends, hang out, and Hopper goes to Daring for girl troubles.

Junior - Dexter and Hopper were already friends and are in many tech clubs together. It's no surprise that they're roommates.

Senior - Northwind and Hopper are both goofy so they would make good friends.

Dexter

Freshman - Daring and Dexter were made roommates because they are siblings. Dexter didn't mind at first since it was like being at home, only they shared a room. It wasn't until Daring's fans kept showing up and Daring getting praised for sports and his looks did Dexter start developing self-esteem issues his father didn't cause him.

Sophomore - Hunter and Dexter are polar opposites in terms of destiny, but they bonded over being good enough, girls they liked, and supported each other.

Junior - Hopper and Hunter are both lovesick fools and video game nerds, so yeah I made them roommates.

Senior - With Alistair's since of adventure and Hunter's knowledge of the wildness, they would try to explore most of the Enchanted Forest and discuss new places to explore.

Courtly

Freshman -No one. She didn't attend Ever After High School until Freedom year.

Sophomore - Crystal and Courtney are pretty diffenet from each other I can see them getting along, but not really forming a bond. Had they met before 'Epic Winter' Courtly would've seen her as another snobby princess.

Junior - Jackie - Jackie and Courtly would get along well since both almost got away with steal another princess's destiny. During 'What's In The Cards for Courtly Jester' Courtly did say Duchess was her friend and the two hangout. They would bond over how unfair they're treated by those with better destinies.

Senior - During 'What's In The Cards for Courtly Jester' Courtly did say Duchess was her friend and the two hangout. They would bond over how unfair they're treated by those with better destinies.

Crystal

Freshman -No one. She didn't attend Ever After High School until Freedom year.

Sophomore - After learning her lesson in 'Epic Winter' Crystal tries to understand Courtly, but they don't really bond.

Junior - Maybe Helga (since I haven't paired her up with anyone)., but the two don't get along.

Senior - Potential roommates for Crystal would be Briar, Ashlynn, Apple, and Maddie. Briar, Ashlynn, and Apple are Crystal's childhood friends (yes, I made Apple her childhood friend too! What was the point of giving her that outfit ?) and Maddie and her became fast friends.

Helga

Freshman - Anyone could've been her roommate and they would not get along.

Sophomore - Before Jackie came along Helga had the dorm all to herself and liked it! Jackie and Helga clash due to both being leaders in each other's family team.

Junior - Helga doesn't really have high opinion on Crystal and the feeling is neutral. The only reason Helga somewhat like is because Crystal keeps her candy cold when she's in the dorm.

Senior - Potential roommates for Helga would be Ginger, but I honestly prefer her having the dorm to herself.

Jackie

Freshman -No one. She didn't attend Ever After High School until Freedom year.

Sophomore - Helga and Jackie were one of the few roommates that didn't get along due to both being stubborn and wanting to be in charge.

Junior - Courtly and Jackie would get along due to almost taking over another princess's destiny and wanting to be in charge.

Senior - Jackie and Duchess bond over being mistreated or looked over just because their destinies weren't as popular as others.

Hunter

Freshman - Sparrow and Hunter being roommates was a disaster due to Sparrow accusing Hunter's dad of being the father of Cerise (not true that was a rumor in Hood Hollow) and Sparrow being a thief. And the rivalry continues to today.

Sophomore - Dexter and Hunter bonded over the fear of not living up to their destinies and making their families proud. Over time they get over that and support each other.

Junior - Hopper and Hunter were an unusual pair to be roommates, but they formed an amazing friendship over sports and video games.

Senior - Chase and Hunter are both weapon specialist and would spare with each other.

Sparrow

Freshman - Hunter was Sparrow's first and only roommate due to Sparrow's obnoxious nature, stealing things, playing his music loudly, and antagonizing Hunter because he thought he and Cerise were half-siblings made him an unlikeable roommate and very unpopular in boys dorms. Maid Marien and Headmaster Grimm struck a deal that if Sparrow could live in his treehouse for the school year he had to report to school early. After that Sparrow never had another roommate.

Alistair

Freshman -No one. He didn't attend Ever After High School until Freedom year.

Sophomore - After Alistair arrived Humphery became his roommate and became friends. Humphery had to explain to Alistair about the technology in Ever After due to Wonderland being behind on tech.

Junior - Chase are both from Wonderland and would bond over that and making their mothers proud.

Senior - I think Northwind and Alistair would be curious of each other's home and talk about different customs.

Humphery

Freshman - Hopper and Humphery became friends instantly over their love of tech and video games.

Sophomore - Alistair became Humphery's roommate after 'Spring Unsprung'. At first it was awkward for the two, but Alistair and Humphery would create codes together that were in the form of riddles and develop a friendship over time.

Junior - Dexter both Humphery are already friends, are in a lot of tech clubs together, and would spend their time on computers.

Senior - Chase and Humphery would challenge each other in brains in chess and other activities.

Chase

Freshman -No one. He didn't attend Ever After High School until Freedom year.

Sophomore - No one, he had the dorm all to himself.

Junior - Alistair and Chase's path to friendship was pretty awkward but overtime they bonded over chess and Chase joined the chess club even.

Senior - Chase saw Humphery as someone who needed a challenge and was impressed that he would sometimes join Jillian daredevil stunts so he tags along.

Northwind

Freshman -No one. He didn't attend Ever After High School until Freedom year.

Sophomore - Gus and Northwind surprisingly got along due to be sidekicks and would share treats with each other.

Junior - He probably had a random roommate he bonded with.

Senior - Potential roommates for Northwind would be Hopper and Dexter.

1.Hopper and Northwind would bond due to being goofy and having bad luck streaks, and ultimately form a friendship.

2. Dexter - Both Dexter and Northwind are overlooked so they bond over that and would be an opposites attract situiation with how nervous/shy Dexter is and How goofy Northwind is.

Gus

Freshman -Anyone really, I doubt they got along.

Sophomore - Northwind and Gus became friends due to being bossed around by family members and love of sweets.

Junior - Had the dorm to himself.

Senior -Sparrow (I what about Sparrow never having another roommate, but I didn't want Gus to be alone). The two would have an awkward relationship since they enjoy stealing and messing with people, but not doing it to each other.

Okay, done! Sorry if some seemed rushed it's kinda hard pairing everyone up.

Prudence and Charlotte

Freshman - It's rare for siblings to not room together freshman year, but the two separated and may have had other villians as roommates.

Sophomore - The two became roommates and it kinda didn't matter to them since they alreay lived together at home and get along.

Junior - Separated again and have a random roommate.

Senior - Like above they have a random roommate.

Huge shoutout to @angelmamoth for telling me I forgot Prudence and Charlotte.