Disclaimer: I don't own Dirty Sexy Money or Grey's Anatomy or Private Practice.

Author's note: Ok, so I thought...why not crossover two of my favourite programmes, especially if the connection is through my favourite characters in both of the shows. And the result was...a Dirty Sexy Money crossover with Grey's Anatomy/Private Practice (because, I mean, come on. Those last two inevitably crossover to some extent, thanks to Addison). Anyway, I thought it was plausible because Karen Darling is a trust-fund baby, and so is Addison Forbes Montgomery, and they both were Manhattanites. And they seem to be in a similar age bracket (as far as I can tell, anyway). So why not make them friends? And the result is this... I hope you guys enjoy reading it. Excessive knowledge of neither show is required really. Please let me know if it's utter shit.

Quick points in case people are really clueless – Karen Darling (Dirty Sexy Money) is friends with Addison Montgomery (Private Practice/Previously on Grey's Anatomy). Addison was married to Derek Shepherd (Grey's Anatomy) for 11 years, until he caught her in bed with his best friend, Mark Sloan (Grey's Anatomy). He left her in Manhattan to come to Seattle, where he met and 'fell in love with' (I interpret this as rebound) Meredith Grey (Grey's Anatomy). Addison followed him there a couple of months later, and though they attempted to make things work, he still loved Meredith. Addison stayed there for a bit longer, until she left for LA to work with her (and Derek's) friends, Sam and Naomi (Private Practice).

So essentially, Derek (and Meredith and Mark) is in Seattle working in Seattle Grace (hospital) and Addison is now in LA, working in a private practice type thing with Sam and Naomi, and a few others. Karen drops by, asks to see Derek and this is the start.

Darling Addison

Chapter I

Derek was standing in the lift, trying to work out what a Darling could want with him. He had finished a (relatively) straightforward craniotomy this morning to meet with the news that one Karen Darling was looking for him. This Karen Darling was not just any woman – she was a very famous and very rich woman. The eldest daughter of business tycoon (and creepy-looking old man) Tripp Darling, she had four divorces to her name, stylish clothes costing more than he could imagine, and money dripping from any words she spoke, he was sure. So what in the world did she want with him?

He shuffled a little awkwardly in the lift, his curiosity rising by the seconds and the lack of answers frustrating him by those same seconds. Finally, the third floor was reached and he brushed past those who needed to stay in the lift. He turned sharply, focussed on the nurses' station because he knew Meredith was busy in the pits and there was no chance she could distract him on this floor...except whenever he thought about her, of course.

Whilst Derek was almost wholly uninterested in rich socialites and their sordid lives, and whilst he could not recall any photos he had seen of Karen (though they were so prevalent that he must have seen them sometime somewhere), he had no difficulty in recognising her as he approached the nurses' station. She wore preposterous heels that reminded him of the heels Addison wore, and her dress, without being scandalous or gaudy, gave off the aura of having cost a small fortune. But it was neither of these things that attracted Derek's attention directly towards Karen. It was her own aura. There was something indefinable that she radiated that turned eyes, even when she was trying to deflect attention.

And as soon as he noticed her, Derek began to feel nervous...just a little. He was wholly at sea as to why she was here, what she wanted with him, and he had no idea how to talk to girls like her; what the hell was he supposed to do?! As he reached closer to her, he realised she was flirting. Twirling her hair coyly around one finger, she was leaning over the station at a male nurse who, it seemed, was close to either fainting or angina.

"Ms..." Shit, what was he supposed to call her? Ms Darling? Ms Karen? Ms Karen Darling? Or was she still married to her latest husband? Shit; shit; shit; shit; shit; shit... He cleared his throat and continued. "Ms Darling?"

She twirled around and he caught the full glare of her charming smile. He found himself smiling back at her as she spoke. "Yes? Can I...help you?"

He felt totally wrong-footed now. Had that been a prank? Hadn't she asked for him? "I'm Dr Shepherd." Well, this had to be better than staying silent. Or so he hoped.

"Dr Shepherd? Dr Derek Shepherd?" Her smile had faded a little, and there was a slightly puzzled look on her face. It still looked charming.

"Yes, that's me."

"Really?"

She seemed to really doubt whether he was Derek Shepherd, and this slightly offended him, he thought. "Yes, that's really me."

"Are you sure?" Her head was tilted to the side now, a little, and Derek found his irritation slipping away to be replaced by amusement. It was almost like talking to a child.

"Yes, I'm sure." His voice held amusement. "I really am Dr Derek Shepherd, you know. I heard that you wanted me?" Oops. That sounded wrong, but she didn't seem to notice.

"Oh. Wow." The wow should have pleased him but it didn't sound like a 'wow' wow. It sounded more like a bad-wow, if such a thing existed, which it clearly did, because she had just said a very unimpressed bad-wow.

"So...did you want me for something?" Again, it sounded dodgy to him. What was it about Karen Darling that made everything associate with sex?

"I don't know." She was still twirling that lock of hair around her finger and looking at him as if she was assessing some specimen under a microscope. Or evaluating an outfit, more likely.

"So...you asked for me...for no reason?" The amusement was fading again, with the irritation sneaking in. How many lives could he have saved in this time? Ok, not even one. It wasn't like his operation took a couple of minutes to perform. But this was still a major waste of time.

"Oh no. I had a reason." She smiled brightly at him, and Derek was annoyed to find his lips responding.

"And that reason was...?"

She leaned forward towards him, and for an insane moment, Derek wanted to close the distance and kiss her – until he thought of Meredith. Before he could move away, she was speaking in a low voice that sounded throaty and sultry to him. "That reason is a reason that I know and a reason that you don't know." She smiles a charming smile that seems wrongly innocent and leans back, and all he can do is smile back, because she is charming.

"Won't you tell me? Even if I ask very nicely?" It's nothing more than a little harmless flirting, and, honestly, he misses the flirting. Not the flirting with random girls he's not interested in, but more the verbal fencing that sends adrenalin pumping to the brain, trying to come up with something witty, and when it was with Addison, something dark and morbidly sarcastic usually.

Karen tilts her head to the other side, and observes him, eyes narrowed a little, and at the end of the observation, all she says is, "I don't get it."

"What don't you get?" Derek would be lying if he said that his interest wasn't piqued. It was piqued. It was very much piqued.

"I just don't get it," Said with a small furrow in her forehead. "I don't get what she sees in you. I don't get what she saw in you to begin with."

"Who?" He was about to add 'Meredith?' but he doesn't, because he wonders the very same thing each time he sees her. What does Meredith see in him? What did she ever see in him? Why is she with him? These questions often give him little panic attacks.

Before she has time to answer, the aforementioned Meredith walks up and he feels everything...just stills. Meredith has that effect on him – the soothing away of all turbulence. She's the calm in the wildest of storms, and without meaning to, she gives him reassurance.

"Dr Shepherd," With the cute smile she keeps just for him.

"Dr Grey," He replies, practically beaming. "This is Ms. Darling." As expected, Meredith gets a little flustered. She gets a LOT flustered, especially under the scrutiny that Karen Darling is putting her through, one very expensively maintained eyebrow raised and the smile on her lips a little disdainful.

"Hi," Karen's voice holds little of the warmth and charm that it held previously, and Derek feels himself becoming protective. "You're Dr Grey, huh?" Her tone feels like an insult, and it does little to reduce Meredith's flustering.

"Dr Grey, is it something urgent or can I meet you in five minutes in my office, to discuss whatever it is that needs discussing?" Nodding a dismissal to Meredith, who mutters a disjointed 'sure' and leaves away, probably with a lot of relief. "What was that about?" There's no cordiality in his voice now. As charming as Karen may be, it was clearly skin-deep.

"So that's the 12 year old?" She was still looking in the direction Meredith had left, but her smile had fully disappeared now. The words ran a bell in Derek's mind.

"12 year old? Wait, you know Addison?"

Her eyes snapped back to his face. "Well, duh. Why else would I want to see you?" Images of various people Karen might know who needed neurosurgery ran through Derek's mind, but he didn't voice it. "Man, you have bad taste. Except Addison has worse taste than you. This just sucks."

In spite of himself, Derek's lips twitched. Karen Darling was nothing if not amusing. "Wh-"

"I mean, sure you're a little tall, but not tall enough for her really, right? And you're hair is pretty nice, but it would look better if it was a lighter shade. And the facial hair is so badly maintained that it makes you look homeless, you know? And you so couldn't pull of Italian. You couldn't really pull off French either. Addison loves Italian and why would she go for you? I just don't get it. Especially considering all the men that were after her..." Her ramble ended with a confused glance directed to Derek, as if really expecting him to give her some sort of an answer.

"You think I'm not good enough for Addison?" That was the bit that got his attention the most. And the bit that pissed him off the most, too.

"No, I know you're not good enough for. Or were. Ever." This pisses him off even more. What the hell? She called him here just to tell him that he's not good enough for Addison? Stupid brain-dead socialite girls are so damn stupid! He decides to voice his thoughts.

"You stupid brain-dead socialite girls are so stupid." He wishes his voice held more venom, but maybe it had greater impact the way it was spoken?

Her charming smile was back in a second. "Oh, but I'm not just a society girl, Derek." When did he give her permission to call him by his first name? "I also know a lot about business. Kind of have to know this stuff, because that's my future. Do you know anything about business, Derek?" He shook his head, her words tugging a smile from his lips. "Are you brain-dead and stupid?" He shook his head again, admitting defeat.

"So you called me here just to tell me I'm not good enough for Addison?"

"Not exactly." He waited for her to continue. "I just...kinda...wanted to see you. I mean, after all the proposals she turned down, she said yes to you. AND, even though you were a prick and a total bastard, even though she cheated on you, despite being insanely monogamous, she tried to make things work with you. I don't know, I guess I just thought you must be something special."

"But I'm not?" Derek was incredulous. He really was incredulous. Without being arrogant, he knew he was good looking, and nice, and romantic, and kind, and considerate. Hell, he was a bundle of love and joy.

"Nope; I'm glad you left her." Yet another statement from the Karen Darling that left him feeling wrong-footed. "It's like the nicest thing you've done for her." She paused to think. "It's probably the only nice thing you've done for her." And after this annihilating statement, she flashed him a glowing smile, and he had nothing to say. What the hell was he supposed to reply to that?

Her phone rang, and irrational as it was, Derek thought the ringtone sounded like a ringtone that cost millions of dollars. He knew it was irrational but Karen Darling radiated money the way an x-ray machine radiated x-rays. "Speak of the devil. Hi, Addison!"

Even without the phone on loudspeaker, Derek could hear Addison voice. "Hiiiiiiiiii, Kareeeeeeen!"She was drunk. If the slight slurring and overexcited voice didn't give it away, the volume of her voice did. Addison was a loud drunk; she always lost the ability to assess the decibels and ended up screaming when she thought she was whispering. She was also an embarrassingly honest drunk. This conversation could be very fun to listen to. Derek's smile grew and curled into something that felt diabolical, even if it didn't look it. This was a conversation he didn't want to miss.

Author's note: I hope you guys liked it. What did you think? Could anyone come up with a more creative name? This was the best I could come up with, alas. So...as far as plot goes...I kind of don't have any. I'm creating it as I go along, but it's going to be a more conversation-character-based story, as opposed to plots. I just love the random things Addison and Karen come out with. And together...well, it'll be like a normal person on some kind of drug, possibly a hallucinogenic one. Which equals humour, pretty much. Anyway, if anyone bothers reading, please, please, PLEASE review it. It's the only way I know I'm doing something right or wrong. This is the end of my late-night-I-should-be-working-on-my-dissertation-ramble.

Also, I'm going to alternate the crossover categories with each chapter, so this chapter is Dirty Sexy Money/Grey's Anatomy. Next one will be Dirty Sexy Money/Private Practice.