AN: This story was originally supposed to be a oneshot, but I had another idea so now it's going to be a compilation of oneshots. They're all going to revolve around Addison and Derek and the Sound of Music. I have no idea where the thought came from, but I really enjoy the musical so I'm incorporating it here. :) Haha. These oneshots are going to be in no chronological order, and will range from really fluffy to really angsty. :)

- I own neither Grey's nor SOM.

Derek walked casually by the row of lockers for the 13th time in the past hour, stealing shy glances at the redheaded girl leaning against it, her head buried in a chemistry book bigger than her face. He had been trying to work up the courage to approach her upon Mark's coaxing. They'd been enrolled in med school for a week now, and the redhead and him had the same classes. She was always seated in front, her attention always fully focused on the lecture. That in itself turned him on; he secretly had a thing for smart girls.

Addison raised her head, her brow lifting at the man who seemed to be stalking her since the school year opened. He wasn't exactly inconspicuous. The hallway was completely deserted and he'd been pacing the front of her locker for the past hour.

"Can I help you?" she asked, her voice containing a hint of annoyance. She looked at him from head to toe, taking note of his over-all appearance.

Derek stopped in his tracks, blushing profusely and unable to form any coherent thought. He was unbelievably embarrassed for being caught fantasizing over the pretty redhead standing in front him, now with her hands on her hips and tapping her foot impatiently, waiting for answer. "Wha—wh… Errr… What?"

Her brow rose further as she closed her book and set it in her locker. "I said, can I help you?" Her hand set itself on her hips more sternly, expecting an answer. The fiery being in her was coming forth, but for the cute man's sake, she was trying to suppress it. "You don't think I notice but you've been following me around for a week. So unless you tell me straight forward what you want from me, I'm going to report you to Student Services."

Derek's face fell, his head telling him to say something smart. "Derek," he said stupidly, inwardly smacking himself for coming up with something so senseless. He shifted nervously in place, staring at Addison's green eyes, wanting nothing more than to get lost in them.

She crossed her arms on her chest, slightly amused by the man standing in front of her. She knew he was a freshman. She knew they had the same classes and that his name was Derek. She knew he was best friends with the manwhore who slept with her roommate just the other night. She also knew he was insanely cute and dreamy, but she wouldn't admit that just yet. "What?"

He cleared his throat, straightening his posture. "My name's Derek. Derek Shepherd. We have Neurology and Introduction to Surgery together." He extended his hand in courtesy.

Addison nodded, uncrossing her arms and extending her hand to shake his. "Addison. Forbes- Montgomery," she added as an after thought, mentally berating herself for even mentioning the Forbes part. Whenever she did, men who wanted to ask her out suddenly went running for the hills, daunted by the mere word.

His jaw fell slightly. "Forbes… Forbes Montgomery?" he asked meekly, his voice a pitch higher than usual.

She smiled, endeared by his reaction. "Yes. Problem?" He was the first man who didn't conveniently have an appointment forgotten, or an emergency to get to right after the Forbes-Montgomery part was mentioned.

Derek shook his head, telling himself not to be intimidated. He reminded himself of his determination. "So…." He buried his hands in his pocket, chuckling nervously

"You want to get to know me, don't you?" she asked knowingly, smirking. She knew she was pushing herself, but if there was one thing she couldn't stand, it was inability to express feelings. She was always good with expressing her emotions, especially her anger, and to see someone battling with emotions to the point of incoherent thought and freaky stalking unnerved her to no end.

He nodded, cursing himself for being too obvious. He really needed a talk with Mark. If he ever wanted to impress her, he needed help. "I do, actually." He flashed her his signature smile, one that was sure to make girls swoon over him.

She smiled. "Okay. Let's start at the very beginning—"

"A very good place to start," he finished, grinning at her.

Addison stopped, her eyes widening slightly. "You know that?" The shock was quite evident in her voice, her jaw falling slightly at the man before her.

"The Sound of Music? Who doesn't?" he asked, his tone quite obvious.

She laughed, thoroughly amused that he knew something that could be considered girly. "You're a man. I didn't expect you to know that. I mean, you could be familiar with it, but to know it?"

He grinned once again and shrugged. "I grew up with four sisters. Count me in for nail polish, hair braiding, and musicals."

Furrowing her brow, she thought it odd for him to be so familiar with things women liked. She honestly had to ask. "You're not… gay, are you? I mean, it's okay that you are and—"

"I'm not!" he protested defensively, slightly embarrassed by the question. It wasn't the first time he was asked that question, but it humiliated him that the girl he liked a lot thought about asking it so straightforwardly. "I'm not, I swear. I mean… come on. I grew up with five women. How could I not—"

"Okay! I get it," she laughed, finally closing the door to her locker and walking toward him. "You're not gay."

He smiled in relief. "I'm not gay. But you're just… getting the do-re-mi of things, right?"

"Right," she confirmed, still amused and bearing that knowing smirk of hers.

"How about we get the do-re-mi's of each other over coffee? Tonight?" he asked, praising himself subtly for the smooth move. "Please?" he added, his voice squeaking slightly.

She found him endearing, his awkward nervousness drawing her to him. Thinking about what she had to do tonight, she nodded. "Sure. Pick me up at 5?" she asked, her tone implying that he couldn't say no. She really only planned to stay in and study anyway.

"Of course. And you stay at…?"

"The apartment just off campus."

"The Booker House?"

She shook her head. "The Ivy Hill."

Derek had to do a double take. "You live at the Ivy Hill? You actually live there?" he questioned, his voice squeaking with disbelief, shock evident in his tone. He didn't know what he got himself into, falling for a girl way out of his league. But she was so kind about it, slightly shy about her social status. It was her modesty that he admired. But nevertheless, he was asking out a Forbes-Montgomery who lived at Ivy Hill and probably owned more Jimmy Choos than anything.

"Is there a problem?" she questioned, sensing his apprehension.

"No… No. I just… I could only dream of affording to lodge at that place. It's so… upscale."

Addison shrugged. "My mom insisted. She hates that I went to school far from home, so living in that place is a compromise."

"And where exactly is home?"

She laughed, touching him lightly on the shoulder. "We'll talk about that over coffee," she said, a twinkle in her eye. "It was nice meeting you, Derek." And with that, she gave him one last smile and walked away, leaving him grinning goofily to himself.

-

He felt slightly out of place at the grand lobby of such a posh venue. His worn-out sneakers and dress-down shirt with his scruffy jeans made him look like a callboy. He would've dressed into something more appropriate, but that totally slipped his mind as he scoured every flower shop in the city, hoping to find the prettiest bouquet. Needless to say, he wasn't able to prepare for the way she looked as she came out of the elevator, dressed in a light summer dress and a cardigan. Her hair was tied to a ponytail, and she had a hint of make-up on her face, making her look like a model right out of a magazine.

Her eyes searched the extensive lobby until they rested on his soft blue ones. She smiled and waved before walking over to him. "Hey."

"Hey," he said, handing her the bouquet of red roses. "These are for you."

Addison smiled and took it from his hands, her eyes darkening for a split second before going back to normal. "Thank you. They're beautiful."

"So are you," he said earnestly, meeting her shy gaze.

She blushed and cast her eyes downward, smiling slightly. "Thank you."

There was an awkward pause between them, neither of them knowing what to say.

"Well, shall we go?" Addison asked finally, mentally berating herself for talking like her mother. Growing up in the lifestyle that she did, old money and certain traditions rubbed off on her that it reflected much in the way she conversed with people.

Derek nodded, offering his arm to her. "There's a coffee place I want to take you to. It's quite near so I hope you don't mind walking."

She shook her head, matching his pace as they exited the building. "Not at all. It's a beautiful night anyway."

They walked to the quaint coffee shop in comfortable silence, both of them lost in thought. It was indeed a beautiful night, the chill just right for New York, and for once, the stars were glittering and showing proudly despite the buildings towering above them. Derek escorted Addison to the plush corner couch and ordered her hot chocolate, reasoning that she wouldn't want to stay awake all night.

"So tell me about yourself Derek," Addison asked, settling herself on the comfortable couch and crossing her legs.

"Well," Derek started, taking a sip of his hot chocolate before turning to look at Addison. "You know that I have four sisters. I'm actually the youngest of the family, and an only boy. I sort of ruined the whole Little Women thing going on."

Addison chuckled lightly, somehow not comprehending how Derek could be straight whilst growing up in a sea of estrogen. "And your parents?"

He frowned a bit before smiling. "My dad died when I was 12. It was sudden, something none of us could have expected. But my mom raised us well."

"I'm sorry," she said sincerely, regretting the question.

"Thank you," he whispered, clearing his throat. "What about you? Any siblings?"

"I have an older brother, actually. His name's Archer and he's two years older than me. He's in med school, too, but he's attendig Harvard Med."

Derek nodded. "Not only are you guys rich, but you're smart too." And with the best genes, he wanted to add, but stopped himself before he could voice it out.

She grinned, leaning back against the chair and eyeing Derek amusedly. "I wouldn't say that… but I'll take it."

He reached for his cup and brought it to his lips once more, sipping the hot liquid cautiously. "What about your parents?"

Addison shrugged. "Here and there. My dad travels a lot. He's a lawyer. My mom is… the epitome of a socialite. She grew up in a traditional upscale household so she says the word darling a lot and adores using the word oh."

"Did that rub off on you?"

"I certainly hope not. But I did get the fiery redhead thing going on from her. She went to a lot of parties while I was growing up, but she's a good mother."

"Ah," Derek smiled, thoroughly amused by the woman standing in front of him. "Can I ask you a really random question?"

She raised a brow at him. "Weren't we just doing that?"

He chuckled. "Well, may I have permission to keep on asking random things then?"

"Of course," she nodded, smiling at him graciously. "As long as I can do so as well."

"Deal."

"Okay, shoot. What's the really random question you were going to ask?" She reached for her drink and sipped it, her eyes transfixed on Derek's powder blue eyes, both endearing and heartwarming.

Derek smiled at her. "Why do you wanna be a doctor?" he asked, looking at her expectantly. She didn't really come off as the type to enjoy gory things, but she looked determined and focused.

She pursed her lips in thought, taking a sip of her hot coco before answering. "I don't know, I guess. It came with the whole advanced placement thing I've been assigned to since I was young. It sort of came naturally, or was expected of me because I graduated high school so early and started college really young. Do you get me?" she questioned, her brow furrowed in slight confusion.

"I'm not sure I do," Derek answered honestly.

Addison chuckled at his truthfulness. "I graduated high school at sixteen, two years before everybody else my age. That's because I attended honors classes and advanced lessons. Everyone made it clear to me that because I was… smart," she said unsurely, "I had the potential to be a doctor. And that sort of just rubbed on me, I suppose. Their dreams for me became my dreams for myself, so here I am."

"But you really want to be a doctor?" he questioned. "I mean, all of the smart things aside, do you really want it?"

She thought about for a moment before nodding certainly. "I do. It's the most rewarding profession there is, and it makes me happy to be able to help people." She uncrossed her legs and leaned forward slightly, eyeing Derek. "What about you, Shepherd? Why a doctor?"

Derek shrugged. "All my sisters are learning to be MD's. And… I suppose I like to be in control."

"With a god-like complex?"

"Maybe. I'm highly competitive."

The night whiled away with them shooting each other random questions, getting better acquainted with each other. Addison had not felt this comfortable with a man before, and Derek never enjoyed the company of a woman as much as he did with Addison.

They were on their third round of hot chocolate, and it was past 8 in the evening when Addison decided she wanted real food to eat. Derek paid for the bill and took her to a hole-in-the-wall Chinese restaurant, the only place he could afford as of the moment.

"I hope you like Chinese," he said earnestly.

Addison grinned. "I love Chinese."

He grinned. "And I hope you eat things other than fine cuisine. This… isn't exactly The Plaza Hotel food type, but it's very good."

"Don't worry about it, Derek. I'm not as high-maintenance as you think."

Derek exhaled in relief, escorting her to a seat and ordering. Once they had placed their orders, Derek straightened his back and stared at Addison who sitting adjacent to him in the small booth. "So… got any talents?" he asked, shooting another random question.

Addison shrugged. "I studied ballet when I was young. And I've appeared in a couple of musicals in high school."

He nodded. "So you sing?"

"Not really. But I used to give music lessons to special kids all throughout my teens. I taught them to play the piano."

"And do-re-mi's?" he questioned, grinning, referring to their earlier conversation on the Sound of Music.

She laughed. "Yes, actually. And you?"

"I play football, if it matters any. All throughout college and high school, I was on the team with my best friend since preschool."

"Mark Sloan?"

"You know him?"

"He slept with my roommate," she said dryly. "He's pretty good in bed, I hear. Or heard. They were… very loud, to say the least. He literally rocked the bed. It kept on banging on the wall."

Derek had to laugh at her expression, one of pure disgust. "Aww, he's a good man, don't worry. I'll introduce you to him sometime."

Her face twisted into a look of skepticism. "That won't be necessary. The next time I see him anyway, all I'm going to remember's how he kept on yelling 'Jesus' or 'God' from across the hall."

"He does that, doesn't he? He's… sexual sometimes."

"He's a manwhore, so you're lying. He's not only sexualy sometimes."

"I suppose you're right," he laughed, excited to tell Mark of a Forbes-Montgomery's opinion of him. "But he's a good person, I swear."

"I'll take your word for it," she said reluctantly. "Anyway…"

"Biggest fear?" he blurted out suddenly, wasting no time to kill the dead air that might come between them.

She was startled for a moment before she thought about the question. She looked at him square in the eye and said, "Failure."

"You don't like to fail?"

Addison shook her head. "I stop at nothing to get what I want. I'm a pretty sore loser."

He nodded, knowing it was his turn to answer the same question. "Mine is… mine's… ending up alone. Sometimes I think my head's too high up my ass to notice things, so people leave me." His voice was sincere, trusting, as if having Addison know his secret could potentially kill him.

She stared at him intensely, trying to read into his words. He didn't seem like the type to commit. In fact, he looked a lot like his best friend, coming off as in love with the thought of life as a bachelor. The revelation was pretty unbelievable. "Really?"

He nodded in affirmation. "I tend to shut myself out when something happens and I… can't really explain it," he said honestly, looking into her eyes for understanding. He knew he probably shouldn't have revealed that piece of information if he wanted to pursue a relationship with the woman in front of him. But for his sake, he was being honest so she could see right through him and accept him for who he was. The reason most of his relationships didn't last long was because he would run for the hills at the first sign of trouble, or obsess over not being good enough to the extent of hurting everyone around him.

Addison smiled at him softly. "I can't say I understand, but, if it makes you feel any better, I don't like to lose," she stated, implying that if he ever shut himself out, she was too much of a force to be reckoned with that she would set him in place.

Derek returned the smile with one of his own, appreciating the words and the implications Addison had spoken. "Well, then I'm glad you're a sore loser. You'll keep me in line."

"I will," she agreed, blushing slightly at his intense gaze. "And for the record, whenever you feel like closing yourself up, you can call me… maybe ask me out on another date." She felt her palms sweat as she awaited his reaction. She honestly wanted to see him again, as more than a friend, and was nervous about him accepting her invitation to pursue her.

He grinned widely, accepting the invitation she was offering with much sincerity. "I'll be sure to remember that, Addison."

That was completely random, I know. And it's pointless fluff. I think all of this is going to be pointless fluff. :)) Tell me what you think, though!:)