Summary: Louise Grant, age 27, is a successful business woman living in Chicago. She's rich, beautiful and wild and she isn't about to change. Until one day, she meets a face from the past...

Disclaimer: I don't own anyone etc etc etc

A different kind of fairytale

There was a consistent buzz about the coffee shop, a murmur that never died down no matter how few or many people were in there. Louise sipped her scalding cappuccino, gently blowing on it before drinking, and surveyed her surroundings. Its light and airy feel along with its of – the – moment minimalist décor was perfect for those living in this wealthy neighbourhood. Business men drank a macchiato whilst busily clacking away at their laptops and impeccably dressed women gossiped with their friends over a latte, reluctantly eyeing the selection of cakes that they could never eat. This was Louise's hang – out, her fail safe spot that she visited dutifully every day after work. Outwardly she was still the same old glamorous Louise, blonde hair professionally cut and dyed, nails manicured, wardrobe full of expensive designer clothes. She often wondered how she ended up in Chicago, it didn't really seem like her type of city when she was offered a job there. She always thought she would end up in a place like L.A or New York, married to a fabulously rich entrepreneur where she could go to clubs and exclusive parties without having to worry too much about working for money. She never thought that she would be the one to end up having a career in business. She had never been particularly goal –orientated at Chilton or college, boys and parties tended to get in the way of actual studying but now, at the age of 27, she actually enjoyed being a career woman.

Letting her eyes wander about the room they quickly settled on a tall dark - haired man who had just entered and was ordering. She willed him to turn around in order to check out his cuteness on a scale of one to ten - some old habits never die –and found herself looking at a somewhat familiar face. It was a pleasant, good - looking face, and put together with the rest of him made his whole specimen the epitome of gorgeousness. There was something familiar about him, something she couldn't quite put her finger on.

"Thanks" he muttered to the barrister, taking his coffee.

Then it hit her. He was Rory Gilmore's boyfriend! What was Prince Charming's name? It was like Michael or Oliver or…Dean. It was Dean, of course it was Dean. He was just as handsome as before, though of course a lot older. To tell the truth Louise had always had a little thing for him while she was at Chilton. He was gorgeous, no doubt about that, but then again so were many of the guys. Something else drew him to her, it was the way he had treated Rory like a princess, he had been so loving and so faithful. Louise had never been one for long – term relationships, too many guys so little time was the motto she had stuck by. But, to be honest, she had always been slightly envious of what Rory had in Dean.

"Dean!" She called. He looked at her curiously. "Oh my God, Rory Gilmore's boyfriend, this is a surprise." He was still looking at her in confusion.

"You probably don't remember me. I'm Louise Grant, I went to Chilton with Rory Gilmore. We met a few times, we met at the dance remember?" She leaned back in her chair, eyeing him flirtatiously. "Please, sit down. What have you been doing these last ten years?"

Dean stared at the alluring woman opposite him. Louise…he vaguely remembered the name but why couldn't he put a face to it? Rory used to talk about her, she was one of Paris' friends. The dance – when did he meet her at the dance? He remembered some very specific things about the dance – Rory was wearing the blue dress that her mom had made for her, he had almost got into a fight with that arrogant jerk Tristan, he and Rory had fallen asleep reading together at Miss Patty's…Stop it, he berated himself, that was eleven years ago. Stop living in the past, we were just kids.

"Louise, hi, of course I remember you." He sat down across form her a little awkwardly. The memories came flooding back. Louise was the one who had flirted with him at the dance. And she was at that stupid Romeo and Juliet rehearsal he had gone to in Stars Hollow. Louise was nice, Rory had said, totally boy - obsessed but she was fun to be around. It wasn't Louise's fault, but her just sitting there was yet another painful reminder of Rory Gilmore and the past Dean was trying desperately to forget.

"Earth to Dean" She snapped her fingers in front of his face.

"What-? Oh, sorry, what were you just saying?"

She smiled at him in amusement. "I was just asking what you were doing in Chicago. I thought you lived in that little hick town of Rory's – what was it, Wood Hollow?"

"Stars Hollow" he automatically corrected. "Yeah I used to but I just needed to get away, you know? I used to live in Chicago, until I was sixteen. I got offered a job here, a really good one, and so I moved here last month."

"What do you do?"

"I'm an architect."

"I'm impressed. Rory Gilmore's bagboy boyfriend has made something of himself. Last time I heard you were married. Have a hard time persuading Mrs Prince Charming to move away from the trailer park?" She winced slightly, did she really just call him Prince Charming out loud?

He coughed and shuffled a bit in embarrassment. She smirked, it was sweet watching him get all self – conscious.

"Actually we got divorced." He said, with more than a trace of bitterness in his voice. "About a year after we got married."

"God, two 19 year – olds got divorced, that's a shocker." She sighed, sipping her coffee languidly. "Oh, no offence" she added hastily.

"Don't worry about it." He mumbled.

"So what happened? It just didn't work out?" she asked curiously.

Dean looked down into his mug. He really didn't want to discuss it right now, and especially not with Louise, an old friend of Rory's that he hardly knew. "I – um, I kinda don't want to talk about it."

"Oh my God, you cheated on her didn't you?"

His head snapped up and he gazed at her in part shock, part annoyance. "How did you know? Did Paris tell you, or – or Rory?" He could imagine them all laughing about it. Poor stupid Dean, they would say, it was a bit of fun while it lasted but you couldn't actually have anything serious.

"You cheated on her with Rory? Woa, didn't see that one coming. Don't worry, no one told me anything, I just guessed. And I won't talk to Rory about it if I ever see her."

He looked relieved. "Good."

"I do have to say you two were like, the perfect couple. It was sickening." She smiled sympathetically at him as he looked down again. "How come you didn't stay together after you broke up with your wife?"

"I don't know. I wanted it too, but Rory had changed. I didn't fit into her world anymore, her Yale college life. She had outgrown me."

They both fell silent for a moment. Dean, because he was trying not to think about Rory, and Louise, because she was trying to figure out what to say without seeming totally insensitive.

"Well, Rory may be brain smart but I think she's pretty dumb when it comes to figuring out guys. Any girl would be a fool to let someone as great as you go." Now it was Louise's turn to blush.

He smiled at her slightly, eyes looking deeply into hers. At that moment Louise felt like they were the only two people in the room. The sound of plates clattering to the floor broke their moment and Louise started to stand.

"I've gotta go. It was great bumping into you Dean. Perhaps we'll meet again sometime, I'm here most days." She smiled and sashayed out of the double glass doors, high heels clacking on the wooden floor.

He watched her go with interest. That was an experience, he thought in bemusement. Louise was not his type of girl, usually. She was far too classy, flirty and forward for his taste. He normally went for simple, cute girls. Girl – next – door types. But maybe he should start broadening his horizon - new city, new start. And that included dating. He shook his head as he drained the last of his coffee. They would never work, she was way too cosmopolitan and beautiful to go for a small – town guy like him. And he wasn't interested in her, of course he wasn't. It was only as he began gathering his stuff that he realised that she had told him nothing about herself.

Louise turned and watched him through the window for a moment as soon as she stepped outside. He seemed lost in thought, brow cutely wrinkling and dark eyes focused on his coffee. God, he was gorgeous.

I was watching season 4 and the episode where Rory and Paris go on Spring Break and meet Madeline and Louise. Lousie says something about Dean being gorgeous and I remembered she always used to flirt with Dean and started toying with a possible Louise/Dean relationship. Reviews love. So review review review!!!!!!!!!