Stupid Cupid
By Jeune Ecrivain
Rating: T
Summary: Jackson Stewart didn't ask to fall in love with his sister's best friend, but apparently, fate would hear none of it. What happens when a skateboarding incident prompts him to go out on a limb?

"Dad, I need your advice."

Robby Stewart resisted the temptation to roll his eyes. "Save it, son," he said. "Just tell me what you want the money for."

"Did it ever occur to you that sometimes I might actually need some man-to-man advice from my father?" Jackson replied indignantly.

"I suppose so," the elder Stewart shrugged. "But more often than not you just want something and you're just trying and failing miserably to be subtle about it."

"Well, this time it's different."

This caught Robby's attention, since Jackson's usual retort consisted of exaggerated protestations to the contrary. "Alright, I'll bite. What's up?"

"It's about a girl," his son responded somewhat sheepishly.

"Keep going."

"Well, I really like this girl. We've gotten to know each other pretty well, and we have a lot of fun together sometimes. She's not like a lot of girls, you know? She's a bit of a tomboy, but in a way that can be so feminine at the same time…if that makes any sense. And she's beautiful, smart, and funny."

"Sounds like you've got it bad. So what's the problem?"
"Well, I kind of kissed her the other day, and…" Jackson began.

"And she didn't take it very well," Robby finished for him, or so he thought.

"No, actually she kissed me back. It was slow at first, but she eased into it pretty quick. But then we were interrupted, and I we haven't really had a chance to talk since," Jackson said, remembering when Miley had arrived home early from the hairdresser and almost caught him and Lily in what was quickly becoming a heated make-out session. "Things have been kind of awkward lately, and it's driving me crazy."

"Well, son, the best advice I can give you is to wait a while and give her some space for a few days, then try talking to her. You just sprung your feelings on her, and she might be trying to decide what she wants to do about it."

"There's more," Jackson said nervously. "This girl, she's…a little younger than me."

Robby cocked an eyebrow. "How much younger?"

"Two years."

The father shrugged. "Well, that's not too bad. The only issue there is how her parents might feel about her dating an older guy. But if you play it safe, I think you can convince 'em to give you a chance."

Jackson looked thoughtful for a moment (a rare sight). "You're probably right," he concluded.

"The important thing right now, though, is to talk to her," Robby reminded him before moving to get up from the couch he'd been sitting on.

"There's more," interrupted Jackson, sounding even more nervous now.

The father gave his son a look as he settled back into his seat. "How complicated does this get?"

"If only you knew," the son muttered before reasserting himself as best he could. "The thing is…she's a close friend of a relative."

Robby cocked an eyebrow for the second time in the conversation. "How close of a relative?"

Jackson scratched the back of his neck hesitantly. "Oh, pretty close, I'd say," he said vaguely.

The response that was on Robby's tongue was stopped short by a knock at the door to the patio. He turned to find Oliver Oken standing outside. "It's open," he said loudly.

Oliver slid the transparent door open. "Hey, is Miley here?" he asked.

"She's at the beach, Oken," answered Jackson.

"Thanks." Oliver turned to leave but turned back momentarily. "By the way, what'd you do to Lily? I've caught her giving you this weird look a couple times today."

"Thank you, Oken," replied Jackson, his voice dripping in sarcasm.

It hardly took a second for Robby to put two and two together. Jackson could practically see the lightbulb over his head as he turned back to face his son with an expression that said quite clearly You have GOT to be kidding me. "You kissed Trescott?!"

Jackson winced. "Maybe," he replied sheepishly.

"You kissed Lily?!" Oliver marveled.

Jackson threw his hands up in defeat. Great. Why don't I just tell all of Malibu?

Oliver blinked. "If something comes of this, could you let me know when you're gonna tell Miley?"

Jackson looked perplexed. "Why?"

"I just wanna see the look on her face!" Oliver grinned.

"Out!" Jackson commanded. "And not a word about this to Miley or it's your head. Got it?"

Oliver smirked before closing the door and walking away to find Miley. Robby was about to ask his son how in tarnation he ended up smitten with his sister's best friend when no sooner had Oliver disappeared than Lily herself walked up to the door looking somewhat apprehensive. She opened the door. "Hey, Mr. Stewart," she said, sounding a little surprised to see him but doing her best to sound cheerful. "Can I come in?"

"Sure, Lily," answered the elder Stewart as he threw the younger a sideways glance. "I'm going to go see what Miley's up to, but I'm sure Jackson can keep you company," he said. Feeling his son's glare on his back as he rose from the couch, Robby said softly and discretely to his son, "This could only happen to you," before excusing himself to look for his daughter.

As soon as Robby was out of earshot, Lily erupted. "You just had to kiss me, didn't you?!" she yelled.

Jackson knew that conversations like the one that was about to occur were never very predictable, but he definitely hadn't expected her to yell at him. "What? You kissed me back!" he protested.

"Exactly!" Lily replied as if it were obvious. "I was doing perfectly fine until you just had to go all romantic on me, swooping me up and nursing my leg like that! Now I have all these feelings that I never knew I had coming to the surface, and I don't know what to do about it!"

Despite his intimidation at Lily's mood, Jackson couldn't help but grin goofily. "You have feelings for me?"

She glared at him. "Yes! Thanks to you and that amazing kiss, my own blissful ignorance about how I really feel about my BEST FRIEND'S BROTHER is out the window!"

The goofy grin returned. "Amazing, huh?"

"Missing the point Jackson!" She took a few steps towards him and stopped. "On the list of awkward situations, having these kinds of feelings for your BEST FRIEND'S BROTHER is up HERE!" She stressed the point by waving her hand high above her head. "I don't even know why you wanted to kiss ME, of all people! I'm not even that pretty or anything!"

"Okay, first of all, you are beautiful," Jackson corrected her sternly. "Second of all, do you think I wanted this? I'm not any more at ease with this than you are! I didn't ask to feel this way about my LITTLE SISTER'S BEST FRIEND! But the truth is, Lily, nobody can help how they feel! I tried to get over you, but there's just something about you, Trescott! You're not like other girls. You're different…in a way that, for whatever reason, I just can't resist."

Lily stared at him, her irritation deflated. "You said I was beautiful," she said in awe.

Jackson's resolve also softened. "Now who's missing the point?" he teased.

"How do you do that?"

"Do what?"

Lily stepped slowly towards him, limping somewhat on her bandaged leg. "How can you be such a dork one minute and so sweet the next?"

He shrugged. "I have my moments."

All trace of irritation was now gone from her voice as she stepped closer still. "Why can't you have more of these 'moments'?" she said, trying to sound indignant.

"Maybe if you gave me a chance, I would," he retorted, drawing closer to her.

"Just do me a favor, okay?" Lily asked sincerely. "No more awkwardness. From now on, let's just be completely open and honest with each other about this."

"Deal."

"Good."

"Lily…"

"Yeah?"

"I want to kiss you."

The slightest pause preceded her response. "I want to kiss you, too," she whispered.

That was all Jackson needed to hear. He wrapped his arms gingerly around her waist and kissed her lips tenderly. He pulled away momentarily before it all became too much for him and he firmly captured her lips with his own. Her response was immediate. She parted her lips blatantly, and Jackson wasted little time in accepting the invitation. Her arms found their way around his neck, and she moaned into the kiss. Jackson hoisted her off her feet and bore her to the couch, where he sat down with Lily straddling him. He stroked her cheeks with his fingers and resumed kissing her passionately. Their lips continued interlocking and massaging each other. No sooner would one kiss end than another would begin.

Jackson and Lily's last coherent thought was I could get used to this.