This chapter was the hardest one I have ever had to write. I knew what had to happen but making it happen in a somehwat organic way was a huge pain. Hopefully it doesn't come off too badly.

Jack ran a tired hand through his hair as he starred blankly out the window of his apartment into the clear night sky. He swirled the scotch in his cup. He took it neat, unable to stand the soft clink of ice cubes in his drink the way his father loved. His teeth ground involuntarily as he thought of his father, and he poured the burning liquid down his throat to wash away the bile threatening to rise. With a tired sigh Jack poured himself another drink and resumed looking out the window.

How was he going to pretend everything was normal when he went back to the hospital? He swallowed hard again, his father had always been able to catch his tells. He couldn't lie to him. He'd never been able to lie to him. Now, he wasn't just going to lie to his father, he was going to betray him. Jacks face twisted in disgust. He'd spent his entire life living to please the man, and now…He pinched the bridge of his nose and finished off the glass in his hand, slamming it down hard like a shot glass, his knuckles almost white around the rim. Abandoning the glass he picked up the bottle; half full.

He was going to inform to the FBI on his father. He was going to be a spy. He took a swig, feeling the effects instantly as James Bonds theme song drifted into his head. No, he thought, it wouldn't be like that, the part of him that wasn't completely trashed reminded him. It wouldn't be glamorous; it was just him, being a rat. He took a long angry swig from the bottle. Did his mother know about her husbands illegal activities, he wondered suddenly, swallowing hard at the thought. How much of his life was a lie? He took another swig, polishing down the bottle till only a fourth of its contents were left.

He groaned and reached into his pocket pulling out his cell phone. Scrolling through his contacts he froze as his fathers name came up. It would be so easy to call him, to yell and scream, and simply be furious; instead he had to be cold and calculating, continuing to play the part of the approval seeking son, dutifully following his fathers every order, while secretly aiding in his arrest. He started to dial, before flipping the phone closed and hurling it angrily into his bedroom, hearing a loud clatter as the phone hit something, causing it to crash to the ground. He winced.

"I should prolly get that," he muttered; not hearing his own slur. His legs betrayed him as he tried to stand, still holding the bottle in one hand and he fell to the floor next to his coffee table. He giggled drunkly, "'pose it can wait then," he added, taking another swig as he lay there. Looking at the nearly empty bottle, his thoughts turned sour again as he remembered why he was drinking to begin with. His hand shook and the bottle tipped over, the contents pooling and sinking into the rug. He sighed. What a waste. Glancing at the clock he groaned and closed his eyes, he had to be at work in a couple hours. Crap.

St. Sebastians; Executive Floor:

Christians fingers drummed lightly on the railing outside his office as he sipped his Irish Coffee and watched the bustling trauma center below him. He heard a scream and a door open with a bang and his eyes flew up to the source of the noise. Jack was applying pressure to a gunshot victims chest as he shouted orders to the nurses and interns around him as the patients blood seeped between his fingers. The blood was all over his hands. Christians jaw clenched remembering Mikhail's words. He had to tell Jack, and soon, or Ben would do it for him. Christian massaged his forehead in irritation. Ben would get into…unnecessary…details. Ben would tell Jack about Australia.

A hint of a smile appeared on Christians lips as Jack stabilized the gunshot vic. His son was a doctor. A good doctor; one of the best actually. Jack shouldn't be a flunky to Benjamin Linus. Christian bristled indignantly; his own life and his sons were rapidly spinning out of his control. He sighed in defeat. There was nothing he could do about it for the time being. He had dug his own grave, and as a result, his sons as well.

He felt a tightening in his chest as he resigned himself to this fate, and made eye contact with a nurse in the trauma center below, gesturing for her to get his sons attention. The nurse tapped Jack on the shoulder and pointed up towards Christians position on the balcony. Jack followed her gaze and his face went blank as they made eye contact. Even from afar Christian could see his sons jaw clench. Christian gave his head a silent jeck back, signaling for Jack to meet him in his office. Without a word Christian turned and walked back to wait for his son.

5 Minutes Later:

Jacks fists clenched and unclenched again as the elevator lurched to a stop. Stepping out he took a shaky breath. He'd barely been able to look at his father since he found out. He didn't know if he would be able to pretend everything was okay during an actual conversation with him. And his pounding head wasn't going to help matters. As Jack entered his father's office he heard the distinctive clink of the ice in his fathers drink. Christian turned from the window to meet his son. He offered Jack a tight, forced smile. Jack gave a stiff nod in return, unable to speak as he felt his mouth run dry.

Christian's eyes darted around the room, as neither was sure of what to say to break the thick tension that was cloaking the room.

"Drink?" Christian offered finally.

Jack swallowed hard looking at the bottle before stuffing his hands in his pockets to keep from reaching for it. "No thanks," he said quietly.

Christian nodded and took a sip of his scotch as the uncomfortable silence returned. "Jack, I'm going to need you to go to a dinner party tomorrow night," Christian said finally, struggling but succeeding in keeping his tone even and formal.

Jack frowned, taking a deep breath to remind himself to keep pretending he was still oblivious to his fathers actions. "I didn't know the hospital was having a fundraiser," he managed.

Christian swallowed hard before meeting his sons eyes, "Its not for the hospital Jack. Benjamin Linus is having a dinner party, and both of us are going to be in attendance," he said calmly, watching his sons face go white.

"Benjamin Linus?" Jack whispered his voice hoarse and his mind racing. He hadn't expected his father to come right out and admit an affiliation to the infamous mobster. Neither, he recalled, had anyone at the D.A's, who had expected it to take months for his father to confide anything to him. He turned away, running a hand over his head. Did his father…did Ben… know that he was aware of his fathers and the hospitals connection to the mob?

He swallowed hard, trying to compose himself before he turned back to his father. He shook his head silently, struggling to make his voice work. "Why," he felt his voice crack, "Why would we be going to a party hosted by Benjamin Linus dad?" he asked, nearly choking on the last word. The lie he was telling as well as the answer he knew was coming made his mouth run dry, and he pinched the bridge of his nose.

Christian licked his lips and drew a deep breath, drawing himself up to his full height. "We're going because we were invited," he said slowly, continuing before Jack could cut him off, "And we were invited because Benjamin Linus is a very old acquaintance of mine," he said stiffly, "And I owe him a great deal," he added somewhat resentfully, hoping his son would understand the implications without him having to spell it out.

Jack gave a hollow laugh, "You work for him," he spat, his face drawn in disgust. Jack swallowed hard, waiting for the response he knew was coming, but needing to hear that his father was really doing this from his own mouth before he went any farther with his own duplicity; but most of all, he needed to give his father one last chance to deny it.

"Yes," Christian admitted after a long moment. Jack let out an angry defeated sigh, and clenched his fist, feeling rage bubble within him.

"Why do I have to go to this party," he asked after a long pause, feeling his heart pound against his chest rapidly; he dreaded the answer.

Christian closed his eyes tightly and shook his head slightly. "Jack, when I started, I didn't know it would be like this, "he started, offering his ignorance as an apology and he reached out towards his son, who jerked away, sending him a look of disgust. "The debt I owe…owed Linus has financially been paid back ten times over," Christian said quietly, licking his lips, "But…what I didn't realize at the time was that Ben was making an investment when he helped me. He was making an investment not just in me, but in my family," Christian said slowly, as his words meaning seemed to get through to Jack who began to shake his head slowly.

"No," Jack said firmly, running a hand over his cropped hair and down over his face. He grit his teeth before jabbing an accusing finger into his fathers Chest. "You did this. Not Me," Christian said nothing, only further infuriating his son. Jack pulled away and turned towards the window, putting his hands on his head, as if he was trying to hold it together as a million questions and emotions battled for control. "I won't do anything for Benjamin Linus," he said finally, his voice raw, "It's your debt not mine. I'm not a criminal," he added scathingly.

"You don't have a choice Jack," his father replied calmly, seemingly unaffected by his sons insinuation. "Ben's made an investment in your future. He's been lining you to follow in my footsteps as the Chief of this hospital since he found out you'd been conceived."

Jack's face paled and he turned back to Christian. "What do you mean since I was conceived?" he all but hissed.

Christian looked at him almost pityingly, "Why do you think I was forced to push you so hard to become a doctor?" he asked sadly.

Jack gave another hollow laugh as his eyebrows raised into the air furiously. "You don't get to blame everything on Linus dad," Jack said vehemently, his hands shaking from trying to contain the swirling emotions in his head, as he tried to tread the line between genuine horror at what his father was revealing and what he was himself withholding. He took a deep breath and pinched his nose, trying to think of a way to escape going to the dinner party.

"You don't have a choice Jack," Christian repeated as if reading his thoughts, "If you don't cooperate you'll be lucky if Ben decides to just kill you and cut his losses," he warned, his voice almost pleading as he hoped his son would see reason.

Jack met his eye and for a long moment, they simply glared at each other, a duel of wills that Jack knew he had to lose but felt compelled to fight anyway. He'd already promised to help the D.A bring his father down, and now he had to do so if he ever wanted to be free from Linus's grip himself.

"I'll see you tomorrow night," Jack said finally, resentfully, before turning on his heel and slamming the door behind him. He felt his hand tremble as he stalked down the hall. Counting to five did nothing. The fear of what he was getting into was gone, at least temporarily, but everything else was still there; the anger, the betrayal. He cursed under his breath, he couldn't work like this, emotional and unfocused. With a sigh he punched out early yet again and headed for his truck. He had to work it out. He had to run.

The Stadium/Later that Day:

Jack sighed as he leaned against his car panting. He took a swig from his water bottle before slamming his fist angrily into the side of his truck. Everything was a lie. He ran a hand over his head and gripped the side of the car tightly. He felt like he was falling, and more and more things he'd thought he knew were slowly unraveling around him. Kate wasn't who she'd said she was, his father and godfather were deeply involved in illegal mob activities, and now, he was suppose to join them in those activities or die-if he was lucky.

"This can't be happening," he muttered, his chest tightening painfully. He sighed, exhausted and drained from the last few days revelations.

He climbed slowly into the drivers seat of his truck and lay his head against the headrest. He pinched the bridge of his nose. He needed a drink. A long drink. He moved to turn the engine on when he caught sight of his glove compartment and sighed again, remembering the second cell phone that was hidden there.

He pulled it out and gave a hollow laugh. It was a prepaid phone with an emergency contact number to the D.A on speed-dial. He was suppose to 'keep them informed' on any 'developments' in the case. He grit his teeth. His father confessing his connection to Linus and bringing him into the fold against his will probably counted as something they would want to be updated on.

He flipped the phone open then closed. He didn't want to talk about this with just whoever was stuck on phone duty for the graveyard shift. Kate's face flashed into his mind and a small smile tugged the corner of his lips despite his mood.

He pulled his own phone out of his pocket and scrolled through the contact list until he came to the number for 'Kate Ryan'. He licked his lips as the number dialed, hoping the number was still in use and making a mental note to change 'Ryan' to "Austen'.

When she answered the phone she sounded breathless, "Hello?" He smiled hearing her voice.

"Hi," he said quietly, his voice thick, stressed, and exhausted.

"Jack," she whispered, sounding surprised, "What's wrong?" she added, picking up on his distress from his tone instantly.

He scratched his head, "I uh," he gave a weak hollow laugh, "I talked with my dad today," he said quietly, his voice cracking on dad as it had all day.

Kate shook her head, searching for words, and swallowed thickly before answering, "Jack, we can't talk about this on this phone line," she warned, feeling a surge of guilt for not being able to be there for him, even if only over a telephone, when he sounded so lost.

He laughed nervously again, "Yeah," he swallowed and nodded, "Right. I'll ah…I'll just go then," he finished quietly.

"No wait!" Kate jumped, "If you need to talk Jack," she shifted, contemplating the words that were on the tip of her tongue. Ana would be furious she knew, but, she licked her lip, Jack sounded horrible. He needed someone and he'd turned to her. "Let me come over?" she offered, smiling slightly in an effort to sound reassuring, "We can talk there okay?" she elaborated calmly, not wanting Jack to be alone when he sounded so confused.

He smiled slightly and let out a thankful sigh, "Yeah," his voice was still thick," Yeah, that sounds good." Kate smiled and went to hand up, "And Kate," he added in a whisper, causing her breath to hitch as she paused, "Thank you."

She swallowed hard, becoming more and more afraid of what Jack was so upset about. "Jack its not a problem," she said feeling a lump again rise in her throat.

Half an Hour Later:

Jack opened the door still dripping wet from a shower, wearing only a pair of sweatpants. She felt her face turn red as he let her in.

"Sorry," he said, pulling a Red Sox shirt on, "I went running earlier," he explained sounding distracted.

He offered her a seat on the couch silently and sat in an armchair next to it. He scratched his head as Kate sat watching him silently, her head cocked in concern.

"It's safe to talk here right?" he asked finally, his head shooting up to meet her eyes, his dark and weary, "There aren't any…bugs…or," he chuckled humorlessly, unable to believe it was a question he actually had to ask someone.

Kate looked down uncomfortably, "No, the DA…we had your apartment swept for bugs this morning," she said apologetically.

Jack chuckled again, "Right," he rocked forward slightly, his brow furrowing further.

Kate frowned watching him struggle. "Hey," she leaned forward, putting his hand into hers, "Talk to me," she whispered her voice thickening.

He looked up slightly, meeting her eyes and let out a jagged breath. Kate felt a lump catch in her throat as she watched his eyes, dark rings surrounded both of them.

He licked his lip as his eyebrows rose, " He called me into his office today, "he stood up and walked to the window unable to keep looking at her, torn between his lingering feelings of betrayal from his relationship with Kate Ryan and his growing desire to hold Katherine Austen.

"Oh," Kate said quietly, she shifted, "Jack I know it's going to be hard to be around him but-"

He cut her off, "I'm invited to a dinner party hosted by Benjamin Linus for tomorrow night," he said quietly turning back to her, eyebrows raised as if silently asking her what he was supposed to do.

"How did that come up?" she asked so quietly he almost didn't hear her.

He leaned against the wall and shrugged. "I just walked into his office and he told me I had to attend the party," Jack swallowed, "And then he said that Ben is apparently grooming me to take Christians place, at both the hospital and as one of his lackies, " he added, his voice cracking.

She stood silently and came over to him. She hesitated for a second, unsure of how he would react given their history, but wrapped her arms around him anyways, standing on her toes to put her head on his shoulder. "It'll be okay, "she whispered, her breath hitting his ear causing him to stiffen momentarily before his strong arms encircled her tightly. He buried his face into her hair as she brought her head back down to lye on his chest.

He shivered slightly and her small arms tightened around him. "Where do we go from here?" he asked quietly, his voice muffled against her hair.

She pulled away, running a hand over her face as she thought of their next step, "The D.A will want you to wear a wire from now on, if Christian wants you in with him, then we need eyes and ears on the whole thing," she said calmly, licking her lip and shooting him a guilty look before continuing, "And you'll have to go to this party," she added, unsure if he was really ready. Jack nodded slowly, trying to let it all sink in, "If your up to it that is," she added, trying to give him an out and hoping he would take it. He didn't look ready to be thrown into the belly of the beast, and she couldn't blame him. Everything he knew had been turned upside down in a just a few short days.

"No," he waved his hand, "I already told him I would go," he let out a heavy breath. She frowned, not convinced it was a good idea. "Really," he added reassuringly, not feeling like the words were completely hollow; in her presence, for the first time all day, he finally was starting to feel like he could breathe again.

She smiled slightly; almost as if she understood the effect she was having on him and walked back to him, taking his face in her hands. "We'll bring him in Jack, I promise. You don't have to work for him," she whispered as she looked into his eyes, still heavy and haunted from the last few days revelations.

He nodded slowly and she smiled, glad he was able to trust her word again. Her breath caught in her throat though as his eyes didn't return to hers, focused instead a few inches lower. In the second it took Kate to comprehend what was about to happen Jack acted. His hands moved from her shoulders to her cheeks, cupping her face tenderly as one thumb gently brushed her cheek, his lips meeting hers with equal gentleness. Quickly however, he was pressing harder, pouring everything he'd been feeling about the case along with his confusion about their relationship into her. Unable to stop him a slight moan escaped her mouth and he moved his head to her neck, flipping them as he held her in his arms, turning so that she was sandwiched between the wall and his chest, her head lulling back against it due to the feelings he was stirring in her.

She wanted to give in, even as his arms held her Kate could remember their night together as if it was happening at that moment; his lips and hands skimming under her shirt, across her stomach… He had meant it then. It had been about them and what they had felt. This was different. It was desperate and despite his initial tenderness it felt cold. There were no secrets between them now. No hidden agendas, no fake names. If there was even a chance of something real, something true, happening between them she sure as hell wasn't going to screw it up by starting their second chance off with this.

"Jack," she whispered, pulling back slightly, breathless, a fistful of his shirt tight in her hand, "We can't," she whispered pleadingly, hoping he would understand why.

He pulled back with a nod, scratching his head before he cleared his throat, his feet taking him slowly towards the door as he did so.

"Jack I-" she wanted to explain, almost regretting her choice as the warmth of his body left hers.

"No, I get it," his voice was cold but his eyes looked wounded and he averted them again quickly, "If something like this were to happen again," he licked his lip, his hand landing on the front door, "You would get taken off the case," he turned the handle.

She paled. That wasn't what this was about. He opened the door with a strained smile as Kate struggled for words, hurt and angry that he wouldn't let her explain.

"I'll call the D.A about what we talked about in the morning," he promised, closing the door on her.

Kate swallowed thickly pushing the palm of her hand against her burning eyes. She took a deep breath as she heard the deadbolt lock in place, trying to convince herself that while his understanding of her motivation had been way off, he wasn't completely wrong. She needed to be on the Linus case. She owed it to Sayid, to Alex, and to herself to see Linus's downfall through to the end. She swallowed hard; even if that meant putting any chance of her and Jack being together on hold.

Jack lay his head against the closed front door, feeling a now farmiliar tightness return to his chest. It had been selfish to kiss her He was an assignment. A asset in a trial, and a means to an end. She needed him to make a case and she had already proven that she would use almost any means to get Benjamin Linus convicted. He felt the corner of his lip twitch up in a smile despite himself, adoring her determination and conviction. He shook his head, he knew better though. Getting into another relationship that had been built on lies was just asking for trouble. His teeth ground together and his jaw clenched as his mind instantly went to memories of Sarah and his father. So many lies. His chest tightened further. He glanced around feeling trapped, relieved to spot an unopened bottle on the counter. He popped the top off easily. He didn't even bother with getting a glass.

Miscommunication and interuptions, Jates two great problems. Let me put it this way, Jate in fiction as well as the show will never be able to be together till they move past those silly love shapes. And yes, that is my not so subtle hint for the next chapter.

And obviously Jack has some massive issues. (Anyone think I need to move this to an M rating?)

10 reviews=update [ And yes, I actually mean it this time, next chapter has the potential for massive coolness]