Summary: AU. Dean Winchester and Chrissie Singer are good friends, and during a weekend stay with their friends they grow closer. Dean has to try to cope with falling in love for the first time along with the usual high school drama. Please R&R!

Disclaimer: I don't own Supernatural or its characters. I only own Chrissie Singer.

A/N: Damn! This chapter is such a long opener! The others may not be as long as this, but they'll be at least 2000 words hopefully.

I'd like to thank luckypixi for helping me with the title!

Hope you enjoy!

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Love is a Complicated Business

~Chapter One: Whispers in the Dark~

Chrissie had just lost her mother. Times were hard for both her and her father, Bobby, the two of them now standing at Karen's grave. Bobby's arms were around his daughter as she sobbed into his chest, Bobby running his fingers through her auburn curls to calm her whilst crying himself. The service ended and father and daughter shared a hug and a kiss on the cheek before turning to their friends.

Chrissie's beautiful brown eyes met Dean Winchester's green ones, a weak almost-smile crossing her full lips as she stepped towards him, her friend winding gentle arms around her before their other friends joined in the hug.

They were all there for her, Sam (Dean's little brother), Jess, Anna, Crowley, Gabriel, Jo, Chuck, Castiel, Jimmy, Becky and even Jo's cousin, Ash.

"We're so sorry, Chrissie," Becky whispered, sharing her own hug with the young girl, "We're sorry."

"Thanks for being here, guys." Chrissie breathed, sniffling and dabbing her eyes as she and the others set off towards their cars.

They headed to Bobby's for the wake, Chrissie spending the afternoon being shown sympathy and care from all her friends, Dean being the last to leave.

"See you at school on Monday," Chrissie said softly, hugging Dean and kissing his cheek, "Thanks for being with me today..."

"Anytime." Dean replied, "See you Monday."

He turned to leave, really not wanting to go anywhere, but Chrissie and her father needed their time alone. Dean's parents and Chrissie's parents had been really good friends, as they had been with Jo's parents. The three of them, and of course, Ash, had grown up together, their other friends coming into their lives in elementary school. They'd all been close since, and now, Sam and Jess were dating in their first relationship, Becky and Chuck were together, as were Crowley and Jo, and Anna and Gabriel.

Everyone wanted Dean and Chrissie to be together, but it just wasn't happening. The two of them were too chicken to admit their feelings to each other, which pissed everyone off, but Crowley had come up with a plan to try and get them together set for the following weekend. It would bring Dean and Chrissie closer, and get Chrissie out of the house. She'd need her own time, as her father would after her mother's tragic death. Karen had died in a car accident, dying instantly, much to Bobby and Chrissie's relief. They'd rather her have died instantly than have her be in a hospital suffering through a long painful death.

"So, my parents are away for a week, and I have that enormous house to myself," Crowley said, Jo chuckling and snuggling up to her boyfriend.

They were all in the dining hall at school, the huge group of them sitting on one table which normally pissed others off, but they should get to a table first if they want it.

"I sense the word 'Party' drifting through the air." She said, Crowley licking his lips and nodding.

"With booze." He said, "And ghost stories about the place, and music, and dancing...and sex."

With that he turned to look at Jo who blushed and kissed his cheek, biting her lip and smiling.

"Okay." She said, "I'm up for it."

"Me too." Dean added.

"Sam and Jess are more than welcome too if you want to ask them." Crowley said with a smile, Dean nodding in response, "But obviously for them...no sex...or booze..."

"Sounds like my kinda party." Ash laughed.

"Yeah, we'll come too." Jimmy said, throwing an arm around his twin brother who sighed and rolled his eyes, "We'll tell Gabe."

"We're up for it too." Chuck laughed, Becky smiling and kissing his cheek.

"And me." Anna added, turning to the final member of the group, "Chrissie?"

"Um..." Chrissie began, "Gee...I dunno, um...my dad kinda needs me at the moment...you know, since we lost my mom and all..."

"Chrissie, you need to get out of the house, love." Crowley said, "Your dad'll probably tell you it's good for you."

"Well, I'll run it by him first." Chrissie replied, "I'll let you know tomorrow."

The others nodded and Chrissie gazed out of the window, her index finger running under her bottom lip and back as she thought. She did miss her mother, but would it be so selfish to try and get out of the house and have a little fun? She'd check with her dad.

"Who's up for going outside?" Jo asked, everyone nodding and getting up, slinging their bags over their shoulders while Dean checked on Chrissie.

She looked so beautiful today, he thought, dressed in dark blue jeans and black tank top, her purple checkered shirt over the top and open, her white and blue sneakers on her feet and hair tied in a ponytail over her shoulder. Her full lips were glittered with a soft layer of lip gloss, no mascara on her eyes which was unusual. She probably hadn't put any on in case she cried. The poor kid had just buried her mother, she and her dad being the only members left of the Singer family.

"Chrissie?" He asked, "You okay?"

The young girl smiled up at him and nodded, slinging her bag over her shoulder and linking arms with her childhood friend and heading out into the yard with him. Chrissie liked Dean. He was always there for her. He was sweet, caring and kind, but all of that was hidden beneath that manly façade of his. He was a strong, brave young man; not one for chick-flick moments, as he called them, but he always had a soft spot for Chrissie. He didn't think the others had noticed but it was obvious to them. He was the one she'd turned to through all her pain and all her troubles, and he'd done the same to her. This weekend would be good for her, but after a few drinks, he knew he'd barely be able to keep his hands off of her.

Crowley's house was a truly beautiful place. It was a large stone mansion, the largest in the city, and he had all these spare rooms to himself. His parents only used a few of the rooms and he was confused as to why the place had so many, but at least when he had a party, his friends could all have their own room and bathroom for the night. Chrissie made her way up the steps outside, texting her dad to let her know she was there, her bag over her shoulder as she was graced with Crowley at the door, a whiskey in his hand.

"Hello, darling." He said, the British accent making Chrissie smile as usual.

"Hey, sweetheart." She replied, kissing Crowley's cheek and hugging him, "You okay?"

"I'm fine," Crowley replied, "You alright?"

"I'm okay."

Within the hour, Chrissie was drunk enough to get up and dance with Becky and Crowley to Only Girl in the World. Quite why Crowley was dancing to that was a mystery to the others, but he, Becky and Chrissie were having fun and making the others laugh. Dean watched Chrissie's smile, taking in how gorgeous it was. It was much better than her crying or looking as down as she had over the past couple of weeks, but it's hardly surprising since she and her mother were so close. Everyone had been paired off into rooms, Crowley pairing Dean and Chrissie together, neither of them noticing his plan. The pair of them really were quite dense about how in love with each other they were. Any idiot could see it.

Castiel had a trick of his own up his sleeve. He tapped Jimmy on the arm, whispering something to his twin who nodded and changed the song to Every Time we Touch. Trust him. Crowley called Jo, a very drunken Ash grabbed Castiel, Anna grabbed Gabriel and Becky called Chuck while Sam led Jess for a dance. Jimmy looked over at Dean who gazed at Chrissie, the young girl looking a little dejected as she moved out of the way of the others.

"Dude," Jimmy began, "Take her for a dance."

Dean looked up at Jimmy and raised an eyebrow.

"Look at her..." Jimmy said, "She looks so alone, go and dance with her, dude!"

Dean sighed, putting his beer down before getting up, seeing Chrissie actually heading towards the hallway with her coat over her arm. He got to her just in time, taking her wrist gently and pulling her towards him.

"Come and dance with me, huh?" He said, Chrissie nodding sadly before putting her coat back over the arm of one of the sofas and sliding her hand into Dean's, "Atta girl."

Dean wasn't a slow-dancer but for Chrissie he'd do anything. He took her into his arms and they danced slowly, the young girl winding her arms around his neck and resting her head on his shoulder, Dean holding her around her upper and lower back, pressing his cheek to her forehead to let her know he was there for her. He'd always be there for her, no matter what. He wanted to be with her so much, but he just couldn't tell her, especially not since her mother had just died.

"Don't go home tonight," He whispered to her, "Stay with us, huh?"

He felt a gentle nod against his shoulder and he smiled.

"You know we're all here for you, right?"

"Thank you."

"Okay," Crowley slurred, "King-sized bed in here...plenty of room for you to fuck..."

Dean rolled his eyes.

"Alright, Crowley, you'd better get back to Jo." Dean said, "Thanks for showing us the room! Bye!"

With that he closed the door, Chrissie giggling at the annoyed sound Crowley made before hearing his call for Jo to 'shake a leg, woman!'. She put her bag on the bed, taking out her white vest top and blue pyjama bottoms, smiling at Dean before heading to the bathroom to get changed. Dean, now that Chrissie wasn't in the room, unfastened his jeans and let them drop, stepping out of them and taking off his shirt, slipping on his sweatpants and folding his clothes up.

He turned to see Chrissie leaving the bathroom in her pyjamas, beautiful auburn curls hanging over her shoulders as she brushed them. Chrissie was met with Dean. Her Dean. Her shirtless, fucking gorgeous Dean. Well...she wished he was her Dean, but she didn't think he ever would be. He treated her like a baby sister rather than a lover and that fact saddened her so much. She didn't want to feel sad anymore.

"Hi." Dean said, Chrissie smiling at him and giggling softly.

"Hi." She replied, moving over to her bag, "I got somethin' a little extra. It didn't get used downstairs so I guess you and I could share it?"

She pulled out a bottle of whiskey and Dean smiled, sitting on the bed with his t-shirt still in his hands.

"Are...are you okay with me sleeping like this or...?" Dean began awkwardly, Chrissie knowing what he meant and raising a hand.

"It's fine, sweetie, don't worry about it." She said, "It's hot in here anyway."

Was it hot in the room or was it just her?

She pulled out two of her many shot glasses she'd packed into her bag and smiled before putting her clothes and other stuff away, her bag going on the floor by the foot of the bed. They got under the sheets, Dean checking his phone to see it was twelve-forty in the morning. There was plenty of space between them, which was good because Dean was struggling to not touch her and hold her, to not lean forward and press his lips to hers. She wouldn't want a boy like him, one who couldn't show how he truly felt because he was scared about what others would say. That made him feel pathetic and weak, but it was true.

"You want?" She asked, pouring her own whiskey.

"Thanks." Dean replied, Chrissie pouring him a glass and handing it to him, "Great party, huh?"

"Yeah." She replied, turning her head as the rain began to hit the windows of the bedroom they were in, "Wow...sounds pretty heavy..."

"Yeah." Dean said, taking the shot down and putting his glass on the bedside table, anything to calm his nerves.

Chrissie took down her shot too and lay back against the pillows, letting out a gentle sigh as her thoughts wandered to her mother.

"You wanna hear something funny?" She asked, turning on her side to look at Dean.

"Okay." Dean replied, turning on his side to look at her too.

"The other morning," Chrissie said, the lump beginning to appear in her throat, "I came downstairs and I asked my dad where Mom was."

Dean looked at her, confused as to why that was funny. It wasn't, and Chrissie knew it wasn't, but Dean knew she'd just said that so she could get it off her chest. She had a lot of stress and upset inside her still over her mother and knowing she'd done that would've made her feel a million times worse. The older teen grimaced as tears formed in her eyes, turning onto his back as Chrissie joined him, resting on his chest.

"Hold me..."

Dean was a little uncertain that this was a good idea. This could send Chrissie a confusing message, but she needed him so he wound his arms around her, feeling hers resting on his chest, her left sliding under his right arm to hold his shoulder. He felt her tears hitting his body and he closed his eyes, unable to suppress the need to kiss her forehead. And he did, tenderly and gently, seeing her look up from his shoulder and gaze into his eyes. They just looked at each other, from eyes to lips and back before Chrissie leaned forward a little, pressing her lips to Dean's.

To say that Dean was surprised was an understatement. Chrissie was kissing him! His Chrissie who he'd waited a long time for was now in his arms, sharing a bed with him and was kissing him. He kissed back, a little unsure, which was uncommon for Dean Winchester, finding the kiss growing deeper. When it was broken, the pair just looked at each other, both a little wide-eyed before they settled, their gazes soft and tender as they looked at each other.

"Dean?" Chrissie asked, feeling Dean's hold on her tighten a little, "What does all this mean?"

"You mean the kissing and the...the cuddling?" Dean countered, earning a nod, "Um...I...I know I wanna be with you..."

The first genuine smile that Dean had seen on Chrissie for almost three weeks shone through and he knew that this was what she wanted too. He didn't know if it would be anything serious but deep in his heart he knew he wanted it to be.

"I wanna be with you too..."

The new found lovers kissed again, thunder coming from outside and lightning's flashes making Chrissie jump and break the kiss. She looked to the window, turning out her lamp while Dean turned out his and rolled onto her side away from him, facing the window. Dean turned over too, winding a protective arm around her waist and feeling her take his hand gently in her own. He kissed her temple and then her cheek, unafraid to snuggle down with her and hold her close to him, reassuring her that he was still here.

"Night, Chrissie."

"Goodnight, Dean."

-TBC-