Max x Chloe: Castlecoming Date

Chapter 1: Finding the Confidence

It seemed like another ordinary day at Auradon Prep, however the school was abuzz with excitement. Castlecoming, the school's biggest event of the year, was coming up in a few days. Everyone was looking forward to it, everyone that is except Chloe Charming. Chloe always dreaded Castlecoming. For most people it was just another party, but for a princess like Chloe it was stepping out into society and representing Cinderellasburg and her family. Chloe always felt the pressure to perform and live up to family's expectations, especially her father's. Her father had been coming down on her particularly hard ever since her older brother Chad had refused the throne and gone off to become a professional tourney player. Chloe did understood why her father was doing this. It was because he felt like her failed with Chad so he was determined not to fail with Chloe even if it meant being super strict with her and giving her impossible expectations to live up to. Chloe sighed. At least her mom was more chill about the whole perfect princess thing, especially after their adventures in Wonderland. Still Chloe dreaded telling her parents her plan for Castlecoming this year because this year things were going to be different. This year instead of going alone like she always did she was going to bring a date. She was planning on asking Max Hatter to Castlecoming. She shuttered at the thought of telling her parents she was going with Max of all people. After all his father was the number one villain in Auradon, not to mention the fact that he had kidnapped her mom and held her hostage along with the Queen of Hearts in the Queen of Hearts palace. Still Max was nothing like his father. He was actually really nice, kind, caring, and sweet. A bit mischievous, but still a good guy. Chloe had really grown to like him a lot. Of course she hadn't always felt that way. When she first met Max sure she had found him attractive, but she had been wary of him because he was a VK and the whole his dad being the most feared villain out there thing. Then there was the fact that Max had created a magic bracelet to turn her evil so he could use her to get the pocket watch and get back at Red, which he still never apologized for even six months after the fact, of course not that Chloe was any better. She thought back to chess game and how when she felt hurt that Red had used her as live bait for the flower Max was only one who noticed she was hurting. He had tried to comfort her, be a friend, but Chloe had not only brushed him off, she had been downright mean and cruel to him when he was just trying to be nice. She felt so ashamed when she thought about it afterwards so she had never apologized for what she had done either. Her thoughts then wandered back to her evil self. She remembered how it felt being consumed by the darkness. At first it had been scary, but then thrilling. She finally felt free. She felt like she could burn down an entire kingdom and not care in the slightest as long as it meant she came out on top. She wanted everyone who had ever wronged her to feel pain. The worst part was it didn't feel like those feelings were purely because of the bracelet. It felt like they came from within her, like all her deepest, darkest thoughts and feelings had come to the surface. Chloe couldn't understand how she could have such awful feelings inside her. She was an HK. She was supposed to believe in the good in the world, not to have anger and hatred in her heart, but yet she hated that world expected her to play a role, the perfect princess. She wished she could just tell the world to go fuck itself and follow her own path, but she had no idea what that looked like. She opened her locker and rested her head on the door and closed her eyes completely overwhelmed by everything she was thinking about. "What am I going to do?", she said with sigh. "What are you going to do about what?", a voice asked behind her. Chloe jumped and turned around. She saw her best friend Red standing behind her. "Oh Red! You scared me!", Chloe exclaimed putting her hand over her heart. "Don't do that!"

"Sorry. Are you okay? You looked stressed.", Red said furrowing her brows in concern. Chloe sighed. "No. I have a lot on my mind especially with Castlecoming coming up.", Chloe said grabbing some books from her locker. "Oh speaking of Castlecoming. I have some exciting news. Luis asked me to Castlecoming!", Red said with an excited squeal. "Oh my gosh! That's awesome Red, but wait he waited this long to ask you? I would have thought he would have asked you to Castlecoming weeks ago.", Chloe said confused. "I know. I thought it was weird too until I saw why. Oh Chloe it was so romantic. He turned the palace tea garden into a flower paradise.", Red gushed. "Oh my! That's so sweet! You have to tell me all about it on the way to lunch!", Chloe said closing her locker and walking away with Red.

As Chloe and Red walked away they failed to notice Max standing several feet away with a bouquet of flowers in his hand. He had been standing there for the past five minutes trying to muster up the courage to go and talk to Chloe and ask her to Castlecoming. He had trying for weeks to find the courage to ask her, but every time he froze up and couldn't approach her. He didn't know what was wrong with him. He was usually so confident. He really liked Chloe a lot and wanted to take her to Castlecoming, but for some reason asking her made him clam up. He sighed and hung his head. "Chickened out again.", he muttered before walking away down the hall and out to the gardens behind the school. He knew he should probably be in class, but he wasn't in the mood, plus class was boring anyway. He sat down on one the benches and put his head in his hands. "Hello Max.", a voice called out to him. Max looked up and saw Chessy sitting beside him. "What do you want Chessy?", Max asked clearly not in the mood for Chessy's games. "Oh I'm just curious why you're so down. Could it be because of a certain blue haired girl? Those flowers are for her aren't they? Let me guess you've been trying to ask her to Castlecoming.", Chessy said with a smirk. "That's none of your business cat and why do you care anyway?", Max snarled. "Oh I don't. I find all that lovey-dovey stuff sickening. I'm just curious why the confident Max Hatter can't ask the girl he likes to Castlecoming. Could it be that you're afraid she'll reject you, that she'll laugh in your face. I mean after all the daughter of a Charming and the son of the most feared villain in Auradon being together, that's absurd. A VK and HK, the idea.", Chessy laughed. "Chloe's not like that. She knows I'm a good person. She knows I'm nothing like my father. She doesn't care about the whole VK thing. It's one of the things I like about her. She's always willing to see the good in everyone even if they can't see it themselves.", he smiled. Chessy made a face and shook his head. "Then why do you hesitate? If you truly believed that then you would have asked out by now. Perhaps it's shame then. Shame that you created a magical bracelet to turn her evil all so you could get a chance with her.", Chessy said jumping onto Max's shoulders. Max's breath caught in his chest. "I have no idea what you're talking about.", he stammered. "Oh I think you do. I see everything Max. I'm always watching. That day at the chess game when you tried to comfort Chloe, she rejected you. Pushed you away. That weighed on your mind didn't it? You knew then that she would never accept you for who you are, that she would always see you as a villain unless she joined your side. That's why you created that bracelet isn't it? Sure yes there was also the getting revenge on Red part, but deep down you believed that if you turned Chloe evil she would start liking you back and you'd finally have a chance with her. That's why you hesitate because you're ashamed to admit that she'll never like you, that she'll never want to be with you.", Chessy said in his ear with a smirk. Max had remained completely frozen the entire time Chessy was talking. "Nothing to say Max? Then you know I'm right.", Chessy laughed. Max clenched his fists and gritted his teeth. Chessy couldn't be right could he? "You're wrong Chessy. Chloe likes me for me. She'll say yes. You'll see.", Max said getting up. "I'm going to ask her to Castlecoming, but first I need to prepare.", he said heading off in the direction of the woods towards the Rabbit Hole. Chessy meanwhile stayed behind laughing. "Yes good. Go. Prepare. Do exactly what I think you're going to do Max. We'll see how long you and the princess's relationship lasts once I'm done.", he laughed once more and then disappeared.