Mr. Frost sat in his large desk chair shuffling through the papers littering his work space. They exampled important charts and statistics, but couldn't hold his attention at the moment. He sighed, thinking that being at the office felt useless if he couldn't do any work.

His eyes roamed around the room, taking in the cherry wood furnishings his assistant had picked out for him. She had a good eye, he had to admit. The pieces may have been slightly more expensive than he had wanted, but she'd brightly exclaimed how well they set colors off in the room when the late light came in the window, and how the warm glow in the room would cheer him up in the last hour of his work day. She said all this with the biggest, prettiest smile, and he just couldn't say no. She looked nothing like his wife, but that bubbly assistant of his reminded him so dearly of Lily.

He sighed. It had been years, but thinking of Lily still sent a numbing sting through his chest, and turned his thoughts immediately to his children. He picked up a photo frame on his desk and walked to the window, staring out at the diminishing sun. He thought of the conversation he'd just had with his eldest child about his continuous streak of unemployment.

Once again, he sighed. He was doing a lot of that lately.

There must be something he could do to fix the situation. He truly didn't mind sending living expenses to Jack, especially with his younger daughter Emma living with him, but that boy needed to open his eyes. He needed to drop the pipe dream he had and work towards a living. And he needed to stop throwing his wife's words back in his face. Always follow your dreams, she'd say. Never be afraid to be happy. They were choice words, of course, but his son treated them less like advice and more like a prophecy. His wife's death had hit Jack the hardest.

He stroked his thumbs over the handmade frame in his hands. The picture showed a young man on the brink of adulthood laughing with a preteen girl on his shoulders, framed in Popsicle sticks and glitter. They both had the same stiff brown hair, his sticking up and hers falling over her shoulders. Mr. Frost laughed, remembering the time Jack had tried to cut her hair and she'd called him crying about her ugly bangs, demanding that Jack be "banished forever."

He wished he could be there with them, but when he was offered the position of CEO to Overland Inc. a year ago after the retirement of Lily's father, the previous chief executive, Jack had wanted to stay in New York. Mr. Frost had worked so hard to reach this goal, and after generations of the Frost and Overland family working side by side, there was no way he could pass up the opportunity. He knew he could trust Jack with Emma; she'd be better off with him anyway since the office would take up most of his time. But before leaving, he'd made Jack promise, promise, that if he didn't want to continue the family business, he'd have to find a steady job before turning twenty. He'd smiled genuinely at his dad and promised, saying it'd be no problem. Jack thought following his dreams would be so easy, he'd definitely reach them in as little as two years. Foolish boy. His nineteenth birthday was only weeks away, and no progression had been made concerning his career.

Problem solving had always come easy to Mr. Frost, but usually only when regarding himself. Other people's problems didn't appear so easily for him, especially when regarding his family. He missed the days when he and Lily were a team, when a quick suggestion from her would set him right back on track. She'd made him a better dad, a better man, right from the moment he'd met her.

He gasped, eyes wide to the reddening skyline. That's it! That's how to fix Jack's problem! Of course, how could he have not seen it sooner?

Jack needed a woman.

Not just any woman, though. He needed a responsible young lady with her head on straight. Someone who could make him pull his head out of his ass and light a fire under it. Someone who could show him the real world, but still keep him as the bright eyed son he loved. All he wanted for his son was to see the way the world works, to find a niche in it, and have his feet stay firmly on the ground.

Then Mr. Frost suddenly realized something: he had no idea how to play matchmaker, let alone do it from opposite sides of the country.

And there it is again, the infamous sigh.

Okay, he thought. If there's a possibility a good woman could fix Jack the way Lily always fixed me, maybe I can find his girl the same way I did. He's going to need an ally.

Mr. Frost and Lily would never had made it through the early throes of their relationship if it hadn't been for Lily's best friend. She'd all but hid around the corner of every date, making sure everything went well. It'd turned out that Lily was just as bad at keeping a good relationship as Mr. Frost had always been, and her friend vowed to help her find the "perfect man." Mr. Frost was in no way perfect, but he'd been perfect for her, and likewise.

All Jack needed was a little push in the right direction from someone on the inside. But where to find someone like that?

Mr. Frost's musings were interrupted by a small knock on the door. He turned, eyebrows raised expectantly, to see the small figure in the doorway. His assistant was an odd thing, always lathered in bright colors and layers of brand names, all while staying in the professional dress code of the company. Today she wore a pink poncho over turquoise pants that disappeared behind dark blue, almost black boots, and a green plated scarf wrapped around her delicate neck. He smiled at the bird pin that clipped up her hair, thinking how she reminded him of an exotic bird herself, always chirping and flitting around excitedly.

Today, though, she seemed anything but exited. She stood timidly on the office threshold, her head lowered and one hand braced on the door handle, as if she were a child waiting for a scolding. She looked up through her eyelashes, tinted with her signature pink mascara, trying her best to seem innocent.

"Yes, Ms. Hy Loo?" he greeted her. "What can I do for you?"

She suddenly let go of her already drooped posture and slumped into the room, sighing. Join the club, he thought.

"I'm so sorry to bother you with this, Mr. Frost, but I need to talk to you about something." She straightened up, deciding on a snap decision that she didn't want to ask him this while looking pitiful. "I'd like to ask you for a raise, sir. I'm having trouble paying for college, and while I have a partial scholarship, my college fund is much too small to pay for it. As you know, I'm entering the medical field to become a dentist, but I'm afraid I won't be able to work here anymore during the school year. I want to start by next fall season, but there certainly isn't enough time to earn as much money as I need. I hate having to ask you for extra help, but I truly need it, sir. You can say no, but I would like to get this out there because it is very important to me." She said this while staring intensely into his eyes, trying as hard as she could to get her point across.

Mr. Frost watched her, his expression becoming more and more puzzled as her speech progressed. She'd been working here for about two and a half years, since June of 2010, before he'd even become CEO. As far as he was concerned, her paychecks were quite high for an assistant as young as herself. Though that may have been partly because she was very good at what she does, and partly because he liked her very much. She was a great girl.

"I was under the impression that you titled for this job to save up for college. The last few years were still not enough?" he asked, surprised.

She looked at the floor sheepishly. "Well, I'm very embarrassed to admit this, but… I was quite irresponsible with a certain portion of the money," she said, trying to use pretty words to make it sound like she hadn't spent almost half of her income on clothes and dentistry books. "Which is why it's painful for me to be asking this of you."

He chuckled. "Painful. Ah, Ms. Hy Loo, you are quite refreshing. You don't know how many people have asked me for raises and haven't thought twice about it. Unabashedly, I'd say. Painful." He laughed again, shaking his head. "Where is it you're heading to college?"

Her wide lavender eyes brightened impossibly more and a smile hinted at her lips, like it wanted to break free and she held it back due to modesty. "Oh, I'm going to NYU. I'm so excited! My boyfriend Aster is staying here, but he's planning on moving up there once he finishes college. I told him there was no point in transferring when he only has – oh, I'm sorry. I didn't mean to jump right into my personal life. You don't want to hear that." She waved her hand to dismiss the topic.

Mr. Frost, unknown to her, was suddenly intrigued. "No, tell me more. You've been with your boyfriend long?"

"Yes, two years last August." She smiled.

"Hmmm. I see… When are you planning on moving to New York?" A light bulb was flickering in his head, and his young assistant seemed to be the unexpected power source.

"I'm hoping to get situated a bit before attending, but if I don't have enough expenses, I won't be able to attend as soon as I would like. I mean, I could – I know there's always the possibility of paying it off through the rest of my career – but I don't really do well with debt hanging over my head. It makes me… anxious." She looked off to the side warily. "But maybe I'll move there… Hmm, perhaps by April? Possibly May? I'd like to see what summer in New York is like." She smiled at him dreamily.

He answered with his own smile, though slightly less whimsical than hers. It was the smile of someone with a proposition on their mind.

"Would you possibly consider moving sooner?"

Her eyebrows lifted quizzically, just toughing the edges of her color streaked bangs. The tone of his voice sounded strange. "Maybe, why?"

"Ms. Hy Loo, I think I may just find that raise for you after all. And I have something to ask you. Please, sit."

This AU is the idea of teensophie-draws (also called arcanabreak) on tumblr. I saw her art/comics, and she so kindly gave me the green light to write it. She'll be writing her own story as well, in drabbles I believe, as well as making more comics and art of the idea. I'll be basing this story off whatever she posts there, but also adding in my own stuff. ;V

Go see her art! It's beautiful! Link on my profile. c: And there's also a link to the playlist on my youtube and her file download for it. Idk how to make it work for iTunes, but maybe you guys do. :/

Reviews are better than cherry wood furnishings.