A/N. So I've never really looked that deep into Oliver's character so this was really hard (but still so fun!) for me. Please review!
A Puppy Named Ace.
1. When he was little, the only thing he wanted in the entire world was a chocolate lab puppy. He wrote several letters to Santa about it, watched Homeward Bound as research, and even picked out the perfect name. But instead of a cocoa colored puppy named Ace under the tree, he got a 64 pack of crayons with the sharpener in the box.
2. The first time Lilly told him about her new jerk of a boyfriend named Lucas, Oliver felt like he had been punched in the gut. The only thing Oliver wanted in that moment was to have just gotten the puppy named Ace instead of those stupid crayons.
3. Once, his mom got shot in the shoulder during a drug bust gone bad. While she was in the hospital, Oliver went out to the convenience store and stole a package of bubblemint Orbit gum, a lemon-lime Gatorade, and a pen in order to get back at the law.
4. He knows his hair is probably too long to be very masculine. Honestly, he does. But a couple of hours before he was going to get it cut, he heard Lilly talking about how cute Joe Jonas was with long hair. He purposely missed the appointment.
5. Oliver knows that Lilly always compares herself to Hannah Montana and Miley Stewart. He knows this because whenever Miley isn't around, Lilly smiles a little bit bigger and laughs a little harder and feels a little bit better about herself. He also knows that Lilly doesn't notice he notices, and it kills him.
6. When Hannah Montana turned out to be his best friend Miley on the beach, Oliver was disappointed. Honestly, he liked Lilly a hell of a lot more than Miley, so what did that say about his biggest celebrity crush, Hannah Montana?
7. Ever since the day he met Lilly in kindergarten, he always keeps a 64-box of Crayola crayons somewhere in his room. The place has changed from the third desk drawer on the right to a shoebox in his closet to underneath the bed. Every night he takes out the box and imagines a big, romantic gesture involving them, but every morning he just puts them in a new hiding place.
8. He absolutely hates being the only guy in their group of friends. He puts up with PMS, shopping sprees, and low self-esteem far too much. Sometimes he doesn't even think it's worth it. But then all three of them will be hanging out, and something will click and all three will start laughing uncontrollably. Then he'll just feel like an asshole.
9. At his seventh birthday party, he had an awesome vanilla cake with race cars in the frosting and seven black and white checkered candles. When he leaned over to blow them out, his sleeve caught on fire. One of his friends yelled out, "You're smokin', Oken!" He's still really glad he decided against inviting girls, otherwise he wouldn't be able to use that nickname anymore.
10. Oliver only started rapping so that he could have his own thing. Lilly was a skater girl, Miley was a pop star, and Oliver was…a donut? But after he started, he genuinely liked it. He couldn't help it if he was fricky fricky fresh.
11. The first time he met Miley's dad, he was shaking in his Nike Air Force One's. The man is a force. But when he heard Miley's mouth open and sweetly call out for her daddy, he couldn't help but laugh. Who still calls their dad daddy at the age of fifteen? Especially a dad who looks like Robbie Ray Stewart.
12. When he was eleven, Oliver swears that he saw a ghost in his room one night. It was a little girl with blonde hair and pj's who kept asking where her Dad went. He ran out of his room and slept with his mom that night. The next day, he sees Lilly at school and she tells him that her Dad left. Four years later, the irony still makes him laugh.
13. Once, Lilly asked him what his best day ever was. He wanted to smile, look her in the eyes and say something super romantic like, "Every day I'm with you." But instead he glances around and says, "What day isn't good? I'm Smokin' Oken, the guy who girls want to date and other guys want to be." Lilly rolled her eyes, and he inwardly smacked himself for being such an idiot.
14. He hates cantaloupe. The texture's weird and the color kind of freaks him out, and all of those nasty little seeds in the middle of the fruit. Yuck. He'd rather have green peas or even cooked carrots over cantaloupe any day.
15. He is aware that guys aren't supposed to believe in things like soul mates and destiny and fate unless they're doing some grand romantic gesture. He usually scoffs at those words when they come up in daily girl conversations. But somehow, those are really the only words he can use to describe him and Lilly. Maybe that's why he's not planning on telling her that he loves her way too much. Soulmates always get together eventually, so why rush it?
16. Rico is a brat. A stupid, spoiled, annoying brat who happens to have hair all-too-similar to Oliver's for his liking. Sometimes though, he feels a little tiny bit sorry for the kid who has a snack hut named after him instead of an actual parental figure. But then Oliver will hear that ridiculous laugh of his and go right back to hating him.
17. He thought that the girls' plan to set up their parents so that they could be step-siblings was selfish and immature. That was like a plot bunny from a bad made-for-TV movie. Plus, if that happened, then he would have to deal with Robbie Ray when he married Lilly. And he wouls so rather avoid that whole scenario.
18. For his sixteenth birthday, the only thing he had ever asked for was a car. He didn't care what kind of car it was. It could've been straight out of the junkyard for all he cared. His parent gave him a computer instead. Yeah, that's just perfect. His life is an old Matthew Broderick movie minus the perfect girlfriend and cool parade.
19. Once, he told Lilly that she was beautiful. It was dangerously close to breaking the "friends only" barrier that they had always had, but it was so worth it when he saw her entire face light up. But then her face clouded over, and that smile quickly disappeared. "You don't count Oliver. You're not a boy boy. You're just my friend boy." He never thought he would be one of those guys who could be completely crushed by a girl. He was so wrong.
20.Oliver knows so many things that Lilly Truscott is good at. Things like surfing, skateboarding, being a good friend, and pulling off crazy hair styles better than anyone else he knows. But what Lilly knows how to do best is to hurt him without even trying, which makes it awfully hard for him to keep loving her.
But he does, more than anything and that's what hurts the most.
There it is. My attempt at an Oliver-centric fic. Please review and tell me what was your favorite!