A/N: Hi everyone! So, here's the thing – I'm a big Addison/Alex fan and, up until this point, all of my fics have been about them. But, when I was writing one of the chapters for my latest Addison/Alex story, I thought that the chapter title (Lady in Red) might make a good Addison/Derek fic. So, I figured I'd try my hand at an Addison/Derek story. I took some liberties with the timeline but, for the most part, I tried to stay as true to the show's timeline as possible. I hope you like the story, and please let me know what you think! Thanks for reading! :)

Lady in Red

Red Hair

It was the first thing he noticed about her. Mark had always been an ass guy. Sam claimed that the first thing he noticed about a woman was her smile, but Derek and Mark both knew that he appreciated a good rack. Derek had always considered himself a legs guy, but when Addison Montgomery walked into his gross anatomy class, the first thing he noticed about her was her red hair. Of course, it didn't hurt that she had nice legs too; but it was her hair that first caught his attention.

It took him two weeks to get up the nerve to talk to her. Mark told him that he was being ridiculous…that he should just ask her out already…that he was a catch, and that there was no way that Addison would say no to him. But, still, Derek couldn't muster up the courage to talk to her. Finally, one day, as luck or fate would have it, he and Addison were assigned to cut open a cadaver together in gross anatomy class. He was completely oblivious to the other three members of the group, as he watched, mesmerized, as Addison made the first incision. She looked up from the cadaver, and their eyes locked instantly. He knew, then and there, that he had to have her.

He caught up with her in the parking lot, after class. "Nice work in there," he complimented.

"Thanks," Addison smiled. "You were good too."

"Thanks," he said with a grin. "I'm Derek, by the way. Derek Shepherd."

"Addison Montgomery," she responded, a slight smile forming on her face.

"Well it's nice to meet you Addison," Derek grinned.

"Yeah, nice to meet you too," she returned. "I guess I'll see you around."

"Hey, Addison," Derek asked, as she turned to make her way to her car.

"Yes, Derek?"

"I was wondering…what are you doing tomorrow night?"

"Why?" she asked with feigned innocence.

"I was hoping you might want to go to dinner with me."

"I'd like that," Addison smiled. "Here's my address and phone number," she said, reaching into her purse, pulling out a pen, and writing down the information on a piece of loose-leaf paper.

"Thanks," Derek grinned, accepting the paper, folding it neatly, and sticking it in his pocket. "I'll pick you up at eight."

"Great; see you tomorrow, Derek," Addison smiled, as she got into her car and drove off. He knew he was being sappy and kind of pathetic, but he couldn't help himself from watching her car as she drove away.

"Well, don't you look like the happiest man in all of New York," Mark teased, as he walked up alongside his friend, ripping Derek out of his daze. "I take it things with Red went well."

Derek smiled. "They did. We have a date tomorrow night."

"I'm impressed, Shep," Mark complimented, as they began walking to Derek's car. "She's hot; nice ass. Of course, it did take you two weeks to get up the nerve to ask her out."

But Derek wasn't listening to his friend. He had a date with Addison Montgomery. As Mark continued to ramble, Derek grinned widely and sang softly to himself:

Addison Montgomery,
He met her in the summer – she
Was cutting up a very dead body.

Red Lipstick

She wore red lipstick on their first date. Years later, she would tell him that the color was called 'Hypnotic Red' and that Dior made it; and he would think that the name 'Hypnotic Red' couldn't have been more appropriate. But, that night, all he could think about was how he had managed to convince Addison Montgomery to go on a date with him. He took her to a trendy Italian bistro. The conversation was good, the chemistry undeniable. But the best part…the goodnight kiss.

"Thanks for a nice evening," she smiled, as he parked his car in front of her apartment.

"I'd really like to see you again, Addison," he said, hoping he wasn't coming off as too eager.

She met his eyes. "I'd like that."

He unbuckled his seatbelt and leaned over to give her a chaste goodnight kiss. Only it didn't work out that way. Sparks flew the moment their lips touched and one kiss quickly turned into two and, before either one knew it, they were passionately making out in his car.

He was still walking on air when he came home from his date that night. And it was Mark's voice that finally pulled him back to reality.

"Good date?" Mark asked.

"Yeah," he smiled.

Mark chuckled. "I can tell."

He looked at his roommate suspiciously. "How?" he asked.

"Well, you've had this ridiculous, lovesick grin on your face ever since you came home. And, oh yeah," Mark added with a smirk, "you've got red lipstick on your collar."

Red Scrub Cap

She wore it for her first solo surgery – a c-section. The blue and white one would come later. He watched from the gallery, proudly, as his girlfriend confidently made an incision and successfully delivered the first baby of her medical career. They would go out for drinks that night, just the two of them, to celebrate. He would smile at her adoringly as she sipped her champagne and talked excitedly about their future.

"Can't you just see it?" she gushed. "You and me…we're gonna be the best in our fields. We'll be world class surgeons, and we'll be put on all the high profile cases."

"I can see it Addie," he laughed. "We're gonna be the best."

"Where do you want to work?" she asked. "I mean, if we're world class surgeons we'll have our pick."

"Where do you want to work?" he challenged.

"I don't know," she admitted. "New York might be nice. I really like it here. How about you?"

He pretended to look thoughtful. "Hmm," he grinned, "I want to work wherever you work."

Red Fingernails

People teased her about it all the time. "Surgeons don't wear nail polish," they'd say. But Addison didn't care; she wore nail polish anyway. "Surgeons don't do a lot of things that I do," she'd shoot back smugly. She was right. Most surgeons didn't wear high heels or designer skirts and dresses to work everyday either…but Addison did.

Her fingernails were painted bright red the day that he proposed. He'd recreated their first date – took her to the same Italian bistro; he even ordered the same meal that he had on their first date, past primavera. After dinner, he drove her back to her apartment, even though she no longer lived there. She'd been living with him and Mark for a while now.

"Derek, what are we doing here?" she asked when he parked his car in front of her old apartment.

He gave her a soft smile. "Addison," he began, "I knew from the moment I saw you that I wanted to spend the rest of my life with you. You're smart and you're kind and you're beautiful. There's a million different things about you that I love – I love waking up next to you every morning and going to bed next to you every night, I love how you watch my surgeries, I love how I feel when I'm with you. I look into your eyes and I see my life…my future, and the only person I want to spend it with is you. Addison Montgomery, will you marry me?"

"Yes," she smiled crashing her lips against his. "I love you, Derek," she breathed when they broke apart.

"I love you too," he smiled. "And, here," he said reaching into his pocket and pulling out a beautiful, princess-cut diamond ring, "I have this for you."

"It's gorgeous," she whispered, as he slipped the ring on her finger.

"It looks nice with your red nails," he agreed.

They sat for a moment in blissful silence, admiring the ring on her finger, thinking about their future together.

"Hey, Addie?" he said softly after a few minutes.

"Yes, Derek?"

"Thanks for saying yes."

Red Roses

She was a gorgeous bride. He knew she would be. But as she walked down the aisle in her Vera Wang wedding dress, holding a bouquet of red roses, she still somehow managed to surprise him with how stunning she looked.

The wedding went by in a blur. Vows were exchanged, champagne was drunk, cake was eaten. It was a big wedding. He had a big family, and since she came from an important family, it was customary to invite other important families. But he hardly noticed the guests at his wedding – Addison was the only person he was concerned with, the only person he saw. And he was okay with that.

"What are you thinking about?" she asked as they danced together that evening.

"Honestly?"

"Honestly," she smiled.

He chuckled slightly and met her eyes. "I was just thinking about how I'm going to remember the way you looked walking down the aisle in your wedding dress, with your bouquet of red roses, for the rest of my life."

Red Eyes

The night she broke his heart she had puffy red eyes. His red eyes would come later that night. He fought the wave of nausea that was threatening to overtake him as she apologized profusely for sleeping with his best friend. He tried to tune her out as she begged him to forgive her. Just looking at her made him feel sick. Hurt and disgusted, he grabbed an armful of her designer clothes and, ignoring her protests, threw them outside into the rain. Then he threw her out. He didn't want to let her back into the brownstone, but hearing her sobs and pleas through the door weakened his resolve. So he let back in, and pulled her into a hug, his arms wrapping loosely around her waist, her arms reaching around his neck. But he couldn't do it. She had broken his heart; the damage had been done. He pushed her away from him, and turned his back to her. He couldn't look at her. When he turned to face her again, she was looking at him expectantly…maybe even hopefully. Her eyes were red and teary and her make-up was running, but he could see the glint of hope in her eyes.

He looked at her sadly. "Okay," he breathed, "I'm going to go. You stay. I'll get my clothes in the morning."

"No. No, no, no," she protested. "We can survive this. Derek, we can survive this. We're, we're Addison and Derek.

"I can't look at you," he admitted. "I look at you and I feel nauseous. I just…we, we, we're not Derek and Addison anymore."

Addison took a shaky breath. "If you go now, if you go now we are not going to get through this," she warned. "If you go now we don't have a chance. We don't have a chance. If you go now, if you go.

He left; hopped in his car and, with a heavy heart, caught the first red eye to Seattle.

Red Dress

She was wearing a red dress the night that he broke her heart. She had told him the brand she was wearing, but he didn't care…about anything that she said. He asked her to the prom…not because he wanted to, but because he had taken her back, so it was what he was supposed to do – what he was expected to do. He knew she looked beautiful. He knew that Karev and O'Malley and even Burke were checking her out. He knew he should have felt like the luckiest guy at the prom, but he didn't. He was indifferent towards her. And then he slept with Meredith. He knew full well that Addison was only a couple hundred yards away, but he slept with Meredith anyway.

Before they had sex, Meredith yelled at him. She told him to stop looking at her; to stop pretending that he wasn't looking at her. And she was right; he had been looking at her. He should have been looking at his wife, but he was looking at Meredith. The funny thing is, though, looking back on that night, he still remembers Addison's red halter dress but, for the life of him, he can't remember what Meredith was wearing.

Red Wine

She was drinking red wine the night they got back together. Three weeks after they had signed the divorce papers, he realized that he had made the biggest mistake of his life. It wasn't like things with Meredith were going badly. It was just, she wasn't Addison. And he wanted Addison.

He nervously knocked on Addison's hotel room door, praying that she'd be there…alone. She opened the door, dressed in navy silk pajamas, a large glass of red wine in her hand.

"Derek," she said in surprise. "What are you doing here? It's Christmas Eve; don't you have plans with Meredith or with your family or something?"

He shrugged and gave her a soft smile. "Christmas makes you want to be with the people you love."

"Derek," she warned.

"I ended things with Meredith," he confessed. "The divorce was a mistake, Addie. I'm never gonna find someone like you again; we've got to give this another chance. We've got to give us another chance."

"Derek, we've had a million lives," she sighed. "It's just…we've hurt each other too badly."

He shook his head. "You know," he began smugly, "the way I see it, we could deal with us in one of three ways."

"Derek," she cut in.

"Option one," he continued, "We could apologize, we could forgive each other, we get remarried, and we could move on with our lives like adults. Or option two, we could apologize, we could forgive each other, we get remarried, but we could still bring up our indiscretions to use against each other whenever we argue."

She smiled. "What's the third option?"

"I don't know what the third option is," he murmured, kissing her softly on the lips, "I just know I still love you."

"Derek, are you sure about this?" she asked, hurt and uncertainty clear in her voice.

"I'm sure," he whispered, pulling her in and kissing her deeply. He could taste the red wine on her lips – the fancy French merlot that she liked so much. He had tasted it on her lips before and, if he got his way tonight, he liked to think that he would be tasting it on her lips for the rest of his life.

"Derek," she whispered when they broke apart.

"Yes, Addison?"

"I still love you too."

Red Pajamas

She was wearing red pajamas the day she went into labor. It was a matching top and bottom set. Once she went on maternity leave, pajamas were the only thing she would wear. She claimed they were the only thing that was comfortable. So she bought a lot of pajamas – she had sets in nearly every color you could imagine. But the day she went into labor, she was wearing her red pajamas.

After thirteen hours of labor, Addison and Derek welcomed Riley Elizabeth Shepherd into the world.

"She's perfect," Derek said, once the doctors had left them alone with their baby girl.

"She is," Addison agreed, smiling lovingly at her newborn daughter.

"You did great," he complimented, placing a soft kiss on her temple.

"We did great," she amended. "But, Derek, look at her…she really is beautiful."

"Of course she is," he smiled. "She looks just like you."

Red Dress

She's wearing a red dress tonight. It's their fifteenth anniversary and, to celebrate, he's taking her out for a fancy dinner and dancing. Riley's staying with Alex and Izzie. Alex is going into pediatrics and neonatology, so they know that Riley will be in good hands. Plus, Izzie and Alex are expecting a baby of their own in a few months, so they need the practice.

"You look beautiful," he compliments her, as they sip their champagne. "Is that a new dress?"

She smiles and tells him it is. She tells him the designer, but he's not listening. But, this time, it's not because he doesn't care. It's because he can't stop thinking about how beautiful she looks and how lucky he feels to be with her…to be able to say that he's been married to her for fifteen years.

"Dance with me, Addison?" he asks softly.

She happily acquiesces, and he leads her to the dance floor. He wraps his arms around her, as they sway to the music together.

The lady in red is dancing with me cheek to cheek
There's nobody here, it's just you and me, it's where I wanna be
But I hardly know this beauty by my side
I'll never forget the way you look tonight

"I love you, Addison," he whispers in her ear.

"I love you too," she whispers back.

I never will forget the way you look tonight
The lady in red, my lady in red
My lady in red, my lady in red
I love you

He leans in closer and kisses her softly on the lips, promising himself that he's going to remember every detail about the way she looks tonight. He smiles contently, as he continues to sway slowly with his wife, the mother of his child, his best friend, his soul mate…his lady in red.