A/N (03/11/15): Hello friends! As hard as it is to believe, it's been about two and a half years since I last updated one of my stories. My sincere apologies to all of my loyal readers for essentially dropping off the face of the earth, and thank you to everyone who kept reading, reviewing, and messaging me while I was lost in "real life", whatever that is!

I am working my way through this story, tweaking it slightly to take it in a direction that will better bring it to the conclusion I always intended it to reach. I'll be posting the updated versions of the existing chapters in batches until it's all caught up and we get back into new material. Most of the changes are minor in the first 15 or so chapters, but there are a few bigger changes in the later chapters of this new version. So even if you've read the story before, I encourage you to start at the beginning and work your way forward - I'll date all the updated chapters as they go up, so that it is clear what has been updated. Thank you all for your patience!

For those who are new to this story - welcome! This is a mostly AU story which begins about 23 years after Season 1; canon events will crop up frequently, but with some twists to fit this storyline.

Addison Montgomery frowned as she stepped into the crowded bar a few steps from the main entrance of Mount Sinai Medical Center, feeling oddly out of place in the space that had once been as much her home as the brownstone where she'd slept each night. Pushing her way through the usual throng of doctors, nurses, and random neighborhood locals, she made her way up to the bar.

"Megan!"

She worried at first that her voice wouldn't be loud enough to be heard over the din of the other customers, but she soon drew the attention of the petite platinum blonde with faded blue streaks in her hair. Shoving a beer at a man on the other end of the bar, the woman smiled and waved at Addison. Tossing a bar towel over her shoulder, she quickly sashayed her way toward Addison's end of the bar.

"Well, would you look at what the what cat dragged in? Where the hell you been hiding yourself all these years, Addie?"

"Sorry Megs, but you know this place isn't really my scene anymore."

Megan shrugged. "Yeah, I suppose we are a little young for someone like you."

"Hey!" Addison protested. "That is not what I meant, and you know it. Besides, I'm younger than you are."

"Age is so much more than a number, darling." Megan waved her hand dramatically, as if to somehow illustrate her point. "Say what you will, Addie, you can go as domestic and mommy-dearest on me as you want, but I know my crazy sister-in-law is still in there somewhere, just waiting for you to let her out."

"Megan Lorene…"

"I know, I know." Megan tossed her hands up in a symbol of defeat. "You're divorced, I know. I got the memo…or the email, as the case may be. Still, I don't care if it's been eighteen years, I don't take to change well."

"Apparently not," Addison said with an amused laugh.

"So, what'll it be? I still remember your old usual." Megan started to reach for a glass under the bar until Addison held up a hand to stop her.

"Sorry, Megs, not tonight. This isn't a social call."

Megan sighed but nodded in understand, motioning to the far corner of the bar. "Back corner booth. But don't say I didn't warn you, I refilled him a few minutes ago and he's in a real doozy of a mood tonight - worse than usual, I'd say, which is saying a lot for him these days. What happened, did someone die on his table today?"

"Nah." Addison shook her head as she stood up, turning her head back toward Megan briefly. "He got promoted."

Megan frowned and started after Addison as she made her way toward the back of the room. She momentarily considered following her, until a drink order shouted from the other end of the bar drew her attention back to her present responsibilities. With a quick shrug, she figured that Addison was better equipped to deal with the brooding man in the back booth anyway.

For her part, Addison felt an overwhelming sense of pity as she slipped quietly into the corner booth, crossing her arms over her chest and staring hard at the man sitting across from her, a half-empty Scotch clutched in his hands.

"You know, for a guy who just got what is most likely the biggest promotion of his career, you look an awful lot like someone just ran over your puppy."

Derek Shepherd didn't even have to look up from his drink to know who was across from hem - only two women would take the time to track him down here, and he knew he sister was tucked safely behind the bar on the other side of the room.

"I don't have a puppy, Addison," he said wearily.

"Oh for the love of God, Derek, it's a metaphor," Addison said. "As of tomorrow morning, you will officially be the Chief of Staff of Mount Sinai Medical Center, Derek. What the hell are you doing here drowning yourself in Scotch like someone died?"

"And just exactly where else would you have me be, Addison? At home? Would you prefer that I was drinking alone in my apartment?"

"Derek…"

"It just feels empty," Derek admitted, pushing the Scotch away as he rested his elbows on the table and buried his head in his hands.

"It's not."

Derek jerked his arm back as Addison attempted to reach out to him. With a quick shake of his head, he looked up at her with shattered eyes.

"I leave the hospital every night and go back to an empty penthouse apartment. It's not my home, it never has been. There's no one waiting there for me. If I never went back there again, no one would notice. And what's the point of that?"

"So what do you want, a roommate?"

Derek rolled his eyes. "You know what I'm talking about, Addie," he said. "I always imagined that when this day came, I'd have a wife to go home and celebrate it with, a couple of kids who'd be there waiting at the door - you know, that life I'd always planned on having, but somehow never got around to building."

Addison nodded solemnly and carefully considered her response, having been through this same conversation with her ex-husband at least a dozen times in the last decade. Their divorce hadn't been easy on either of them - no one would have expected that it would be after more than sixteen years of marriage. She felt grateful that, in the intervening years, she'd at least been able to move on in a way that seemed to have somehow eluded Derek. For years, she'd told his sisters to be patient with him, that eventually it would pass for him too, but in the eighteen years since their divorce had been finalized, Derek had seemed to only retreat further and further within himself.

"You can't live in the past, Derek," Addison said. "We tried, we really did, you and I both know that. Five whole years we tried after…after Mark…and Seattle…we tried a lot longer than we should have, probably. We just…"

"We weren't meant to be," Derek interrupted knowingly. "I'm not trying to go back to that, Addie. You and I, we were finished a long time ago. It's just…I don't know what it is, really. Sometimes I wonder if after the divorce, I buried myself too deeply in my work, if I somehow forgot to live my life. I've come this far in my career, I've got everything I always said I wanted professionally, but what do I have to show for it? What else do I have in my life except for the job?"

"You've got your mom and your sisters."

"Right," Derek scoffed disbelievingly. "Look, I get that they love me because they have to, but let's not kid ourselves here, Addison. My sisters aren't exactly my biggest fans these days. I see Meg because she owns this place, but beyond that, I think I've seen the others maybe twice since the holidays last year - if that."

"And whose fault would that be?"

"Don't even start," Derek sighed, knowing exactly where she was going when her eyebrow arched up accusingly. "I know it's my fault, I'm not as dumb as you seem to think I am. That doesn't change the fact that my sisters are not in my life, not anymore, and even my own mother's getting pretty fed up with me."

"You could change that," Addison suggested gently. "They all still adore you, Derek, even if you've neglected them terribly. The holidays aren't that far off. Why not go home and spend them with the girls this year?"

"So that I can spend a week getting nagged about how I need to settle down, how I'm wasting my life away alone in the hospital? Trust me, Addison, I get enough of that from inside my own head. I don't need to hear it from my sisters too. The only reason I put up with it from Meggie is the discount on the booze."

"You'd better not let her hear that, not if you value your life," Addison said. "Even if you don't count your sisters, you've still got me and Julia - and Ryan too, even if neither of you will admit that you're actually friends."

Derek shook his head and picked his drink up once again.

"Ryan and I are not friends," he said after taking another sip. "You don't become friends with your ex-wife's new husband. That's not the way things work in real life."

"You also don't have someone you're not friends with be your daughter's godfather, so how do you explain that?"

Derek shrugged. "You've got that man wrapped around your finger, Addison. He did it because you asked him to, not because we're friends."

Addison leaned back in the booth and stared hard at the man across the table from her. If she hadn't witnessed the changes happening with her own eyes, she never would have believed that this was the same man she'd married more than thirty years earlier.

"Come on, this pity party has got to stop, and it's got to stop right now. You've got a lot of good things in your life, Derek Christopher Shepherd, and it's about time you opened your eyes and saw them."

"None of it's the same, Addison," Derek said dejectedly. "It all feels like something's missing - like I was supposed to have something else or be somewhere else or…something. I can't explain it, but it drives me crazy. I lay awake at night staring at the ceiling, running through all the choices I've made, over and over and over again. I can't stop wondering, if I'd done even one thing differently…"

"Like what?"

"I don't know," Derek admitted. "But one thing, somewhere along the line – if I'd turned left instead of right, stayed behind of leaving, would my life be different now?"

As she watched him ramble on, it suddenly hit Addison exactly what – or more specifically, who – Derek was lying awake at night wondering about. When they had first begun trying to be friends again after their divorce, it had been somewhat painful for her to hear him go on and on about the young woman who seemed to have so completely captured his heart during those few short weeks he'd spent alone in Seattle. Now, though, it just saddened her to see him hanging on that memory like a life preserver, unwilling - or maybe even unable - to let go and move on.

"You're thinking about that intern again, aren't you?"

"You think I'm crazy, I know. We only had a few dates, and they weren't even real dates. But there was just something about her, Addison. I knew it the moment I laid eyes on her in that bar. I don't know how to forget her. I can't shake the feeling – what if she was the one, and I let her slip through my fingers?"

"Derek, it's been more than twenty years since you left Seattle. When are you going to stop daydreaming about this woman, get off your butt and fly back there? Go see your intern, find out what she's doing. You're only making yourself crazy wondering."

"She's moved on. I missed my chance, Addison, our moment passed."

"Then let it be in the past, Derek. You can't have it both ways, though – if there's a possibility of anything with this woman, you have to take that chance. If there's not, if it's a moment that passed, let it be that and start living your life again. Take a vacation. Spend some time with your family. Go on a few dates, even."

"Just drop it, would you?" Derek snapped. "Shouldn't you be getting home to your family anyway?"

Addison shrugged, leaning across the table to place a chaste kiss on Derek's cheek as she stood up.

"Be that way if you want. I just wanted to congratulate you on the big promotion. Try to celebrate a little, would you? At least talk to Megan, because so help me God, if you walk out of here tonight without telling her about your promotion…well, you know it won't be pretty."

Derek stumbled slightly as he stepped into his apartment in the early hours of the morning, his sister following closely behind him.

"Go home, Meg."

Derek collapsed onto the couch, not even bothering to turn his head to look at her as he spoke. Turning around, Megan quietly closed the front door and fastened the deadbolt, ignoring Derek's mumbled protest as she walked past the couch and into his kitchen.

"I'm sixty years old, Megan, I can take care of myself."

Returning to the living room a few minutes later, Megan silently set a cup of instant coffee, a glass of water, and a bottle of aspirin on the coffee table in front of her brother. Taking a seat in the easy chair across from the couch, she leaned back and stared at him with no small amount of pity in her eyes.

"I don't need a babysitter."

"Then what about a baby sister?" Megan finally broke her silence, causing him to snap his head up to look at her.

"You're not much of a baby anymore, Megan."

"I'm still a hell of a lot younger than you are, old man."

Derek shook her head. "Not tonight, Meg."

Megan sighed as Derek shook off her attempts to draw him into their usual playful banter. She knew he hadn't been happy in a long time - heck, their whole family knew it. Still, he usually managed a better show of it that he was putting on tonight, and the fact that he wasn't even trying had her worried.

"Addison says you've been talking about your intern again."

"She was never mine."

"Well, could she have been?"

Megan had always been curious about the mysterious woman her brother had been so fixated on since his return to New York twenty years earlier. She knew Derek thought that he'd fallen in low in Seattle, but although Megan was certainly the most optimistic and romantic of the Shepherd sisters, even she was sure he was living in a fantasy.

"I don't want to talk about this, Megan."

"You never want to talk about her, Derek," Megan pointed out. "You won't even tell us her name, but you'll still get drunk and go on and on about she could have been the love of your life. Quite frankly, it's getting old. So either start talking or I'm done."

"Don't let the door hit you on the way out." Derek motioned with a flourish toward his front door.

"I'm serious, Derek. If I walk out that door, it's over. I'm done. You're my brother, I love you, but I won't stand around and watch you self-destruct like this. I'm not asking for much, Derek, I just want you to talk about it."

"And I told you, I don't want to."

Megan stood up, grabbing her purse off the floor and tossing it over her shoulder. Standing just above where Derek was sitting, she looked down at him, holding back the tears that were building in her eyes.

"Last chance, Derek. Let me in. Let me help you. Please…please, Derek, let me help you."

"Get out, Megan."

Megan took a deep breath and nodded slowly, biting her lower lip to keep her tears at bay.

"If that's the way you want it, fine," she said angrily. "You always were a terrible drunk, Derek. Just don't forget what I said - this is it, it's over. Don't bother coming by the bar tomorrow night, either. You're free ride's over."

With that, Megan took one final look at her brother before hurrying out of his apartment. As the door slammed behind her, Derek slumped forward and let his head sink down into his hands, knowing that he probably just thrown away the last good connection he had left to his family.