A/N:I'm having serious trouble waiting until Wednesday, that promo was really amazing. It's only like 10 days until the finale and then another long hiatus...I am seriously going to have trouble coping. Here's hoping for some Jate in 5x15 and the finale. I've had enough of this angst lol, they need to start talking again.

Thank you so much for all the reviews. My finals are almost finished with, and so soon you should be more frequent updates until this fic is finished. I have some ideas I'm mulling over for my next fic, and I'll be sure to let you all know when I know where I'm going. With that said, here's Chapter 14. Hope you like it.

Chapter 14: The Right Moment

The next day at work had been rough for Jack. No matter how much he debated in his head whether or not to follow Charlie's advice, he still couldn't make up his mind. He'd had a few chances today, namely the ride to the hospital and lunch in the cafeteria, but both times he'd doubted himself at the last second and decided not to say anything.

As easy as work had been today, Jack couldn't recall a single thing he'd done all day- besides think. He was relatively sure he had gotten absolutely nothing done his entire shift, something that had never happened to him previously.

But it was now or never, they were riding home and Mark was sure to stop by later to ask Kate to go with him to the hospital's annual staff awards ceremony. If he didn't ask now, he'd be stuck waiting on the sidelines, prowling the bar, and he didn't want that. And that was assuming he managed to get over the fact that he wasn't there with Kate, which he highly doubted. Jack didn't think his heart would be able to handle it.

Mustering up all the courage he had in him, he turned off Arcade Fire on the car radio and looked over at Kate, who returned his gaze in confusion.

"Why'd you turn off the music, Jack? I love that song." Kate asked.

"Crown of Love? Really? You don't strike me as that type of person…." Jack began, his voice trailing off. Pull yourself together Jack- ask her!

"Not what type of person?" Kate asked, raising her eyebrow at him in mock hurt.

"Not the type of person that…." Jack began to explain, "Never mind. It doesn't matter. I was just wondering if you heard about the hospital's annual staff party?" He asked feeling more and more confident as each word left his mouth.

"Yea, Sandra told me about it. Why d'ya ask?" Kate replied.

"I was wondering…if uhh, you're going." Jack stammered out. He felt like a high school student asking a girl to his first dance.

"Uhh, yea I think so." Kate said. She still hadn't told Jack about Mark. To be honest, she wasn't sure if she wanted to.

If he found out the reason they'd broken up, it might lead to him becoming even more distant, and that was the last thing she wanted. The last few weeks had been so perfect, that was the last thing she wanted to do.

"Oh ok, never mind then." Jack said curtly.

If she's going then that means Mark's asked her. I waited too long. It's over. Good job, Jack.

"Are you going, Jack?" Kate asked, ignoring Jack's tone. She may not have wanted to tell Jack about Mark, but she was going to try and convince him to ask her.

Jack smiled, "Well, I hadn't decided yet." He said, and stopped, letting the silence envelop them.

There followed an awkward silence, and within seconds Kate turned back on the stereo, and "Creature Fear" by Bon Iver could be heard clearly through the speakers.

I was full by your count,

I was lost but your fool,

Was a long visit wrong?

Say you are the only,

Why did this song fit so perfectly with Jack's emotions? He had known on the island that he loved her, and he had thought she felt the same way. He was empty before her, delving into work, but Kate…she made him feel…complete.

So many foreign worlds,

So ready to be full,

So ready for us,

So ready for us,

A creature fear,

But then she'd told him just how wrong he was- that she didn't love him, and that shattered him. It was the reason that, to this day, he had trouble opening up again. Jack wasn't sure if he could endure that pain again.

I was teased by your blouse,

Spit out by your mouth,

I was lulled by your low,

Seminary song

Now Kate's back in his life, and yet again, he's confused. Her actions are telling him one thing, while her words portray another. As the song finished, he asked himself what he was supposed to do?

The next song that came blaring through the silence between them was "Mercy" by OneRepublic. What the hell was it with this radio station? It was like someone somewhere really wanted Jack to listen.

Angel of Mercy, how did you find me?

Where did you read my story?

Pulled from the papers, desperate and hurting,

Seeking a momentary fix.

Jack had been a broken man, consumed by his career before the crash, before Kate. She had been his escape from all that, the first true happiness he'd experienced in years. When they'd parted ways, all that emotion evaporated, and misery resumed. He could only hope it didn't last forever.

All I wanted to say, all I wanted to do,

Is fall apart now,

All I wanted feel, I wanted love,

It's all my fault now,

A tragedy I fear.

Jack got the message loud and clear. Now was a time for confidence, not indifference. He wanted this more than anything, and now it was time to fight for it, not let it go only for it to end in tragedy. Charlie was right.

Jack turned off the stereo and turned to Kate.

Kate looked back at him with the same confused pout she'd given him just minutes earlier when he'd turned off "Crown of Love".

"Well… see I was going to do this really awkward thing where I ask this girl who's already got a boyfriend to the party, but then I found out she was already taken." He said, hoping she'd get the message.

"Is that your way of asking me to the dance, Jack Shephard?" Kate asked, smiling broadly. Apparently she had.

"Well, it was. Pretty lame, huh? But you're already going, so it doesn't really matter does it?" Jack said, defeated.

"I am taken." Kate replied cryptically before muttering to herself, "Hopefully."

"See what I mean? I can't exactly take Mark's girlfriend can I?" Jack said frustrated.

"Well, lucky for you, I'm not going with Mark." Kate said, Jack still not understanding what she was getting at, and that fact made Kate grin.

"Well, I can't think of anybody else from the hospital who could have asked you already, and just so you know, I'm not going to ask why you're not going with Mark. I'll let you two sort that out on your own." Jack reasoned. "You'll tell me about it when, and if, you ever want to."

"I can think of one person." Kate said, laughing because Jack couldn't take the hint.

"Dr. Palmer?" Jack inquired; he really was clueless.

"Eww. No." Kate said squirming in her seat. "He's like 60." She joked.

"Dr. Russo?" Jack asked again.

"No, but you're getting closer. My date's a surgeon too." Kate explained.

"I dunno, Kate. I give up, who are you going with?" Jack asked.

"Well, you'll have to ask me again first. Then I can tell you." Kate said flirtatiously.

"What are you talking about, I just did. What are you playing at?" Jack said honestly.

"Are you serious, Jack?" Kate gave him a dumbfounded look. "I thought a little common sense was a requirement for surgeons?" She joked, hitting him playfully on the shoulder.

Then it hit Jack like a ton of bricks, "Oh. You want to go with me…" Jack said, more to himself than Kate.

"Yes, Jack. Jeez, I thought I was going to have to find another date because you might not have figured it out by the time the party started." Kate joked, laughing playfully as she turned the radio back on.

"Good thing I did get it eventually, I was beginning to think I'd need a date. I've been trying to ask you all day, just couldn't find the right moment." Jack said truthfully as they pulled into the driveway to their house.

"It'll be fun, Jack." Kate insisted, and Jack agreed.

"Yea, it'll be fun."

I'm so lost in you,

A tragedy seemed to be over now,

A tragedy it seemed to be.

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"Kate, we really have to. It's supposed to start in 30 minutes." Jack yelled from his place on the couch.

In typical male fashion, it had taken Jack less than thirty minutes to shower and put his suit on, while Kate had been upstairs for the better part of two hours getting ready.

"I'll be right down Jack. Keep your pants on." Kate yelled back.

Jack chuckled to himself, and grabbed the remote. He turned on Sports Center to hopefully catch the highlights of the Red Sox game that was supposed to have finished just a few minutes ago.

Sure enough, within moments the highlights were up- and it wasn't good news.

"Damn A-Rod." Jack groaned as he turned off the TV. He began to sit and wait for Kate to finish getting ready, and his mind drifted to thoughts of how tonight would go.

Would he finally tell Kate how he felt? Would she feel the same way? Would she push him away? Jack hoped he got the chance to find out.

"So, how do I look?" Kate said interrupting Jack's thoughts.

Jack stood up from his position on the couch and turned around to face Kate. "Wow." Was the only word his mouth could muster.

"Wow? Is that it?" Kate asked, smiling.

"Sorry. You look…amazing…hey, isn't that the dress you bought for Mark?" Jack asked, relieved he'd found a way to move the subject from his reaction to Kate's appearance.

"I don't remember buying any dresses for Mark, Jack." Kate insisted.

"No, no. I specifically you remember saying…" Jack began, but didn't get the chance to finish.

"It's a very special dress, for a very special person. Since when does that automatically mean Mark?" Kate added playfully, looping her arm in Jack's. "Now, we going or what?"

Jack pulled his car into the parking lot of the ballroom that was hosting the annual ceremony. It was a beautiful place, laid out perfectly for the night's festivities. It even had ample private spots outside in the event Jack had the courage to admit his feelings to Kate.

Because Christian had helped overseen the planning of the party, Jack was privy to the night's basic schedule. There would be a cocktail hour to begin the night, followed by a buffet style dinner, and finally to end the night, there would be the hospital's annual award ceremony. The hospital gave awards for recognition in research advancements, improved treatments, and extraordinary cases including surgeries and diagnoses.

Jack was determined to find the time to tell Kate how he felt about her tonight; he just needed to find the right moment. He could take her outside, alone and peaceful, and let his feelings loose. He just hoped she would reciprocate them, or it would all have been for nothing.

After some thought, Jack figured his best plan of attack was to find some privacy with Kate during the cocktail hour. If he waited any longer, he feared she might have to much "fun" and not be thinking straight.

The pair of them walked inside, and in the dim light of the ballroom Jack couldn't help but think she looked even more stunning than she had at home. The dark green silk highlighted her eyes, and Jack had never seen anyone look as beautiful.

After taking a moment to long to take in Kate's appearance once again, Jack placed his hand on the small of Kate's back and led her over to the tables. They were headed towards a relatively empty table when Kate heard a voice from behind her.

"Kate!" Sandra yelled, waving her hand in the air. "Over here, I saved seats for you!".

Kate turned around smiling, and Jack whispered, "Looks like you two are getting along pretty well, huh?"

They walked over and took their seats next to Sandra and her boyfriend, and within five minute of incessant gossiping, Jack could tell finding 'the right moment' would be harder than he'd originally thought. It looks like his original plan had just been thrown out of the window.

Jack spent the majority of the night by Kate's side introducing her to various people he knew around the hospital, including the perennially cold Christian Shephard.

To Jack's surprise, Christian seemed generally interested in what Kate had to say, and if he didn't know better he'd venture a guess to say that he approved.

Jack left the pair of them together, alone, for a few minutes when he went to buy them some drinks, but to his relief, when he returned they were still chatting away, enjoying themselves.

After greeting what seemed like the entire hospital staff, Jack decided it was time to make his move.

"Hey, Kate. You want another?" Jack said, pointing towards Kate's drink.

Kate smiled back at him and nodded.

Jack returned seconds later with two drinks in hand and handed one to Kate.

"To friendship." Kate said out of the blue, holding her glass up.

Jack, feeling like his world was tumbling down, awkwardly held up his glass to hers. "Yea… cheers." He replied, downing the entire drink in one go, immediately craving another.

There followed an awkward silence while Kate glanced around the ballroom and Jack reflected on what she'd just said. He was extremely close to giving up.

"Jack, we should probably get back to the table, I think it's almost time for dinner." Kate suggested, and Jack nodded in agreement.

"Yea, good idea. I'm starving." He smiled weakly following Kate to their seats.

Their table was eventually called to the buffet and they filled their plates.

Kate took the vegetable lasagna and a small side salad, while Jack took the Filet Mignon.

They settled back into their seats and began a conversation throughout dinner. They had touched on various subjects about work and life, when Jack realized he had never found out why Mark wasn't here this evening.

"Kate, if you don't mind me asking, where's Mark tonight?"

"Oh. Well, the truth is we broke up a few days ago, if you could even call what we were doing dating." Kate said stifling a chuckle and she stared down at the table.

"Oh, I'm sorry to hear that. I really hoped you guys worked out." Jack lied.

I wish he knew how much that hurts, Kate thought. "Yea, me to." Kate agreed.

"Did he tell you…" Jack began.

"Kate, we're going to get some drinks." Sandra informed her friend, arm wrapped around her boyfriend, "we'll be back for the awards." She said and led him off towards the bar.

"Sorry, Jack. What were you saying?" Kate apologized.

"Oh, just asking if Mark told you why it wasn't working?" Jack asked sincerely. He couldn't see any reason why Kate wasn't good enough for Mark, he couldn't find a reason she wasn't good enough for anyone.

"Not really. Just kinda said it wasn't working." Kate lied, not ready to tell Jack the real reason behind their break-up.

Taking all of this information in, Jack mustered up all his courage.

"Kate, can I tell you something." Jack said.

"Sure, Jack. Anything." Kate replied.

"Alright. Since you got back…" Jack began emotionally, but the moment unfortunately ended abruptly.

"Shush, Jack! The awards are about to start! I think you're going to win something." Kate whispered, putting a finger to his lips.

"Later?" Jack asked quickly.

"Yea, we can talk about it later. Right after the awards." Kate assured him softly, turning her attention towards the stage.

Dr. Christian Shephard has made his way up onto the stage to begin presenting awards. It was a long, drawn out process, with each recipient giving a short speech. The whole ceremony had taken about an hour, and Christian was about ready to wrap it all up.

"Ladies and gents, I have one last award to give out today. It is the State of California's Emerging Surgeon Award." Christian began.

Upon hearing this, Jack shot Kate a look, and she smiled knowingly in return. Apparently her and Christian had gotten along very well when they'd met. Usually Christian enjoyed keeping secrets from everyone.

"It is my honor, to present this years award, to my son, Dr. Jack Shephard." Christian announced, and the ballroom erupted into applause.

Jack didn't know what to do; he'd never been publicly recognized before. He looked at Kate for assistance, and she said, "Go on. Get up there." gesturing towards the stage.

Jack obliged and strode slowly towards the stage, eventually embracing his father and grasping the award.

"Wow." Jack began, "This is really a surprise. I'm not really sure what to say, I mean…I like to be a man of few words, so I guess I'll keep it short. It means a lot to be recognized by other surgeons…jeez, this is harder than my first surgery. But that's a story for another day." Jack continued, laughing to himself. "I guess I'd like to thank everyone at the hospital, my dad, and especially Kate Austen, my best friend. Without you, I don't think I would've gotten through the last few months of my life."

At the words 'best friend', Kate's heart skipped a beat. She couldn't possibly have hoped for anything more, but that's exactly what she wanted. Kate knew she probably didn't deserve it, and for the first time in her life, that bothered her.

Jack walked down from the stage and returned to the table to find Kate waiting for him. They hugged briefly and then both sat down while Christian concluded the ceremony. After a few minutes, the ceremony was officially over and the guests began filing out after saying their many goodbyes.

"So, is it later yet?" Jack asked jokingly.

"Yea, what did you wanna tell me?" Kate replied, interested.

"Let's go outside. Little more private." Jack suggested, taking her hand to guide her outside.

They found a relatively secluded part of the facility, adorned with a small fountain. Kate and Jack both sat down on the rim of it, and gazed into each other's eyes.

"Kate, since you came to my house that one night a few weeks ago, my world got turned upside down. I lost you once on the island, and then…when Sawyer…came along, I lost you again." Jack began nervously.

Kate nodded, silently begging for him to continue.

"When I saw you, I thought, 'I'm not going to lose you again.'" Jack continued.

Kate smiled slightly, "What are you saying, Jack?"

Jack took a moment to compose himself, smiling to himself, then stated, "What I'm trying to say Kate, is…"

"Kate! There you are! Some of the girls are going out for drinks, sort of a ladies night. You wanna come?" Sandra yelled running over to her friend.

Kate didn't immediately respond, instead looking to Jack, almost asking for permission.

Jack nodded solemnly, switching his gaze from Kate's eyes to the stone floor underneath them before downing yet another drink. Apparently what he had to say would have to wait.

The right moment had eluded him once again.

A/N: That's it for now. I'm sure most of you wanted to see it happen this chapter, but I couldn't resist. Please review, tell what you liked/hated, I can take constructive criticism...it'll only improve my writing.

Coming Up: Jack reflects about the night's events and makes a decision, with a little help.

Oh, and EternalConfusion, I swear you read my mind :).