A/N: So this is for JD Phoenix. It's her Christmas present. She didn't ask for anything specific but she mentioned a sort of theory she had for Lackson and I ran with it. I hope she likes it! It's way longer than I thought it was going to be! Enjoy!

Some Hearts

By angellwings

I've never been the kind that you'd call lucky.
Always stumbling' around in circles,
But I must have stumbled into something.
Look at me,
Am I really alone with you?

-"Some Hearts", Carrie Underwood

"Jackson?" Lilly asked as she saw who was on the other side of her apartment door. "What are you doing here?"

"Hiding. Can I come in?"

"Miley Stewart's brother comes to Miley Stewart's best friend's apartment to hide? You really think that's gonna work?" Lilly asked him with a smirk. "There's probably at least one photographer out there who knows you're here."

"I'm not hiding from the press. I'm hiding from Miley," Jackson sighed. "The last place she'll look for me is here. Can I come in?"

Lilly's brow furrowed. "I—"

"And don't you call her either. I need some Miley-free time. I'm not a terrible big brother. it's just every now and then I need to be away from her insanity."

Lilly smiled secretively at him. "Come on in. Just try not to destroy my beautiful apartment while you're here."

Lilly closed the door and shut her blinds before turning back to Jackson. "You know, you're not the only one who needs Miley-free time. Why do you think we don't live together any more? It was too much even for me."

"Yeah, well since Siena and I broke up she's been in top annoying little sister form. First, she tried setting me up with other girls, then she tried scheduling me 'play dates' with Oliver, and now she's trying to get me back together with Siena. I really just wish she'd leave me alone. But she's convinced—"

"That you're unhappy?" Lilly asked.

"Yes!"

"Try being the ex-girlfriend of your best friend's current boyfriend," Lilly said with a laugh. "Her guilt alone is enough to drive me crazy. I mean there was a full year and a half between Oliver and I breaking up and her and Oliver getting together. I honestly didn't care. I was happy for them, but she was convinced that I just had to hate her on some unknown level."

"What did she do to you?" Jackson asked curiously.

"She set me up with Gabe Lammatti."

Jackson laughed. "Wait. Hottie Lammatti from high school?" He paused. "I'm ashamed that I know that nickname."

"Yes, she tracked this guy down and talked him into going on a blind date with me," Lilly said with a roll of her eyes. "Neither of us had spoken to or of him in years."

"That's my sister for you. Crazy as chicken with its head cut off," Jackson smirked. "She gets that from me, I think."

"I think you both get it from your dad," Lilly told him with a grin.

"If we get it from him than he gets it from Mamaw. So blame her."

"Oh, I do. Every day."

"You know you're not exactly sane either, Truscott," Jackson pointed out.

"True, but I wouldn't get in as much trouble without you Stewarts around," Lilly said teasingly. "Can I get back to my story now? You'd think she'd leave it at that. But no. Both she and Oliver came on the date to make sure 'everything went perfectly.' Like I'd never gone on a date before. Would you like to know how it ended?"

"Let me guess…badly?"

"Oliver spilled pasta salad on Gabe's head."

"On purpose?"

"No, I wish. That would have been less embarrassing. He tried to do the table cloth trick. You know the one where you pull the table cloth out from under the dishes?"

"Wow, nice to know fame really hasn't changed the guy. Still dorky as ever," Jackson said with a laugh.

"So, you see, I need Miley-free time too. Hence, this beautiful apartment," Lilly said with a smile. "It's my sanctuary."

"And you let me in?" Jackson asked in shock.

"You sounded like you needed a sanctuary too. But back to the thing I'm really curious about. Why don't you want to get back with Siena? You do remember that she's a 'B-b-bikini' model right?" Lilly asked teasingly.

Jackson sighed and ran a hand over his face. "Yes, I remember. But I don't want a bikini model anymore."

Lilly's eyes widened and she gasped. "What?"

He huffed. "I want normal. You know? I want to have a job where I can stay in one place and have a set routine, and I want some one in my life who wants the same thing. I want that 'Hi, honey! I'm home!' kind of life. I want someone to come home to every day—"

Lilly gave him a glare and he knew what she was going to say. He continued before she could interrupt him.

"—Or I want someone to come home to me everyday. Either way, I just want something wonderfully average. I want the house, the dog, and the two point five kids. I could never have that with Siena."

Lilly nodded in understanding. If it was possible she saw Jackson in a completely different light now. He actually seemed sort of mature. It was bizarre.

"What about you?" He asked. "I don't think I ever found out why it didn't work out with you and Oliver."

She smiled sadly at him. "I couldn't do it anymore."

"Do what?" Jackson asked. He sat down on Lilly's couch and motioned for her to join him.

"I couldn't be the girl waiting on him to come home, and I couldn't see me waiting on him for the rest of my life," Lilly admitted. "You said it best. I wanted normal. I wanted a normal relationship. One where I was in the same place as the guy, where I could actually see him on, at the very least, a weekly basis. And Oliver didn't want that. So, we decided to break up. And I think we're better off for it."

"Well," Jackson said as Lilly finally sat down. "Will you look at that?"

"What?"

"We actually have something in common."

Lilly laughed. "We've always had things in common, Jackson."

"Yeah, but I've never really noticed before now."

"Wow, you're such a boy," Lilly teased.

"I've been told."

Silence stretched out between them, and not a comfortable companionable silence but an awkward agonizing silence. Both of them seemed to be trying to think of something to say. There was lots to talk about but neither seemed to know how to express themselves in a way that wouldn't be embarrassing. Lilly studied the light blue throw on the back of her couch while she thought and Jackson was content to try and figure out the abstract artwork on Lilly's coasters. Jackson sighed and Lilly cleared her throat.

"So, would you—"

"Maybe I could—"

"Sorry."

"Go ahead."

"No, no," Jackson said with a shake of his head. "You go first."

"I, um, was just going to ask you if you'd like something to drink."

"Oh! Yeah, sure. Anything," He told her. "But no diet sodas."

"Okay, orange soda sound good?" Lilly asked as she headed to her kitchen.

"Perfect," Jackson said before he looked down at Lilly's white couch. He could just see himself spilling something on it. "Um, you know what…do you maybe have a clear beverage of some kind? Like Sprite? Or even water would do, really."

Lilly peeked around the open door frame. "A…clear beverage? I mean I have Sierra Mist but if you want orange soda—"

"No, no. Sierra Mist will do just fine."

"Okay," Lilly said as she gave him an odd look. "What were you gonna say?"

"Hmm? When?"

"Before when we both started to talk," She said as she came back into the living room with one glass of Sierra Mist and a glass of orange soda.

"Oh, um, it's not important, and kind of awkward," Jackson admitted.

"Jackson, we're 'kind of awkward' people," Lilly told him with a laugh. "What were you going to say?"

"I was just going to ask if you even really wanted to be in a relationship right now," He stated nervously. "But you don't have to answer that. It's none of my business, really."

Lilly bit her lip. "I—I don't know. I mean I'm not actively looking for anything at the moment, but I wouldn't automatically disregard any options that came my way. You?"

He blinked. He was surprised she'd answered. "I—I, um, wouldn't mind. I'd just rather find the girl myself. On my own terms. Not Miley's."

Lilly grinned teasingly at him. "Oh yeah? Found anybody yet?"

He laughed nervously. "No, not yet. What about you? Anybody made you any offers?"

She sighed. "Nobody that really flips my switch, unfortunately."

Jackson chuckled. "Flips your switch. I like that. I might have to steal it."

"Feel free," Lilly said with a wave of her hand. "You could also use, 'floats my boat.' That's a good one."

Jackson laughed. "Turns my knob?"

Lilly let out a loud burst of laughter. "That one strikes me as very awkward for some reason."

"Preaheats my oven."

Lilly laughed again, and Jackson kept going.

"Butters my skillet. Oh! Or butters my biscuit! I think I like skillet better though," He said thoughtfully. He turned to Lilly. "Judge?"

She took a breath to calm her laughter. "Skillet is much better than biscuit."

"Good call," Jackson said as he laughed with her.

Lilly laughed softly for a few more moments before she smiled at him. "You're a strange one, Jackson Stewart."

"Thank you?" Jackson said in an unsure tone.

"I mean that in a good way."

"A good way?"

"The best way," Lilly told him honestly.

"What does that mean exactly?"

Lilly stared at him for moment as she considered what to say. "It means that you're different and that I—I don't know. I mean you're Jackson."

"Hey!" He said angrily. "I don't know if I like the way you just said that. First you say I'm strange in a good way, and then you say I'm different, and then you say my name like I'm some sort of bumbling idiot. Make up your mind, Truscott. Which one am I?"

Lilly stayed silent for a long moment. Jackson sighed and stood up. "You know what, I can take this kind of abuse at home. I'll see you around, Lilly."

He started to walk away and Lilly went after him. "Jackson, don't leave. I didn't mean it the way it sounded."

"Then what did you mean? Because it didn't come off as very positive."

"I just meant that I'm not sure about what I mean. I think I know, but then I think…you're Miley's brother. A part of me feels like it would be wrong to say what I think I mean," Lilly said with a sigh. "I didn't mean to hurt your feelings."

"You didn't hurt my feelings," Jackson lied as he puffed up his chest.

Lilly grinned at him. "Sure, I didn't."

"Not the point," Jackson said as he cleared his throat. "I want to know what you really meant. I want to hear the thing you're afraid to say."

Lilly let out a shaky sigh. "Well, you're different than any other guy I know, and I think—I think you might be something I need in my life right now. That was the thing."

"That doesn't sound so wrong," Jackson said with a smirk. He shrugged. "In fact, it sounds pretty great to me."

She gave him a small slow smile. "What?"

"I'm not saying we should date or anything. I mean not unless that's what you meant, and if that's what you meant then I'm all for it. I just meant—oh geez. Can I start over? I just meant that I think at the very least being better friends would be a good thing. Unless, you meant that you wanted to date, I mean. But you probably didn't because I'm Jackson and your Lilly and Miley would freak…right?" Jackson asked as he began to pace.

"W—we could date," Lilly answered hesitantly. "I mean one date wouldn't hurt anyone."

"You think?" Jackson asked as he took a step closer to her.

"Yeah, I mean we wouldn't even really have to tell anyone."

"I just see one problem we might have to deal with," Jackson told her with a small grin.

"What's that?" Lilly asked as she took a step toward him.

"There's probably going to be more than just one date, and around the time we get to our fourth date we're gonna have to start telling people," Jackson said as his grin grew into a smile.

Lilly bit her bottom lip and then smiled. "You think we'd have more than one date?"

"Didn't you hear me? I'm not just predicting more than one date. I'm predicting a relationship," Jackson said flirtatiously as he finally stood with in inches of Lilly.

"A relationship?" Lilly asked teasingly with a smirk. "So you want a relationship now? I might have to think about this. That's a lot to ask of a person after one freakishly honest conversation."

Jackson shook his head. "I don't think so, and even if it is I'm pretty sure you can handle it."

"I can?" Lilly asked as she reached out and looped her arms around his neck.

"If anybody can, it's you," Jackson said as his own hands wrapped around her waist.

"Hmm," She said with a teasing grin. "That's something to think about I guess."

Jackson brought one hand up to cup the side of her face. "Why don't you think about this too?"

Lilly quirked a brow at him but before she could say anything Jackson's lips had captured hers. She made a startled sound, and tightened her arms around his neck. He deepened the kiss and she finally relaxed into it.

When they pulled apart she chuckled. "Oh yeah, there's definitely going to be more than one date."