Summary: AU. When Millie gets asked out on a date by Dean Winchester, she knows that this is pretty important to her and she can't even figure out why. She doesn't expect to be so upset when he can't make the date. What does it all mean? Please R&R!

Disclaimer: I don't own Supernatural or its characters. I only own the Reiner family.

A/N: I was inspired to write this when I was busy watching When Harry Met Sally which is now one of my new favourite movies! It's funny, cute, romantic and more enjoyable than I thought!

Hope you enjoy this fic and please review!

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When Millie Dated Dean

-One-

He could see her standing on the other side of the yard with her friends, Jo, Anna and Becky.

He'd always seen her as the spitting image of Meg Ryan at the start of When Harry Met Sally, although he'd never admit that he'd seen that film. Millie Reiner was the prettiest girl he'd seen in a while and she was new here.

It would be nice to take her out...Get to know her. She seemed to be one of those good girls who wouldn't easily let a guy into her pants, like Jo Harvelle and unlike Meg Masters.

He started to approach the girl with the big blonde curls and the gorgeous misty green eyes, the full, luscious lips and the figure to die for. Her skin was pale and looked so soft that Dean just wanted to run his hands over it. She was wearing a light purple long-sleeved, grey jacket and dark blue jeans with her small purple pumps. She looked nice in purple.

"Millie?"

Jo, Anna and Becky shared looks as Millie turned, smiling sweetly at Dean. Dean Winchester was a boy with a one-tracked mind and they knew what he was going to see Millie for.

"Hi, Dean." She said softly, Dean grinning at her.

"Hi, Millie." Dean replied, "You okay?"

"Yeah, thanks, are you?" She countered, brushing her hair over her shoulder with her beautiful slender fingers.

"Yeah. Just wondered if you wanted to go out tomorrow afternoon, maybe to the park and then for some dinner and a movie tomorrow night?" Dean said with that ever present, handsome Winchester smile and charm, "Drive-in or cinema. Your choice."

"Oh, um..."

Millie wasn't used to being asked out on dates by many people. This could be a trick for all she knew. It wouldn't be the first time someone had tricked her into thinking she was going on a date.

"I'll let you choose the movie too." Dean said with a soft smile, "I'll even sit through a romantic comedy for you."

Millie smiled, the look in Dean's eyes just telling her that his intentions were truthful. She nodded, Dean grinning and nodding in return.

"Pick you up at one-thirty?" He asked, Millie smiling in response.

"Alright." She said quietly, trying to hide her blush, "Thank you."

Dean winked at her and walked away, Millie finding her sweet self being swarmed by the girls who giggled and chatted to her excitedly. She found herself being commanded to join her friends on a shopping expedition after school that day.

"You need something pretty. It suits you better." Anna said.

"But nothing too Mary-Sue." Becky said, the others shaking their heads at the fanfiction reference.

She was obsessed.

"But, Millie is a Mary-Sue!" Jo laughed, Millie gasping.

"I am not!" She protested, "I don't have a dark past!"

"No, but you're a goody-two-shoes." Anna chuckled, Millie blushing in response, "I think he liked the way you looked in purple. We'll get you a purple top."

The eighteen year olds wandered through the mall, picking out make up and outfits, one after the other pushing Millie into dressing room after dressing room.

She couldn't believe that the girls were making so much fuss over her, it was just a date. But as they reminded her, it was a date with Dean Winchester, the school's sexiest and most popular boy. You didn't screw around with Dean Winchester and not every girl got asked on a date with him. You had to be rather special to get a date with Dean Winchester.

God, how much more nervous that made her. Dean Winchester was such a Casanova, and his reputation made him out to be a real lady's man. Millie was nervous, excited and also wary. Dean wasn't one to wait before making his move on a girl, and as attractive as Millie found him, she knew she couldn't let him just ravish her. She had to play hard to get.

"Mom?"

Millie's mother, Isabelle rushed from the kitchen with a huge smile on her face. Millie and Isabelle were very similar in looks and attitudes and Isabelle therefore could read her daughter like a book.

"What's his name?" She asked, Millie biting her lip, "C'mon, I know you have a date! What's his name?"

"Dean Winchester."

Isabelle gasped and gazed at her child with sparkling eyes and a beautiful smile.

"Dean Winchester?" She asked, "Wow. You got something nice to wear?"

Millie rushed to her shopping bags and pulled out the three tops she'd bought, one purple, one pink and one blue. Isabelle gasped and laid each one against Millie's chest, the two of them giggling excitedly.

A date with Dean Winchester!

Millie couldn't wait.

-TBC-

Hope you enjoyed!

Thanks for reading so far!

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