Chapter 30: Derek's Second Rebound Date

Derek woke up early the next day and glanced out the window at Meredith's house. He watched for a few minutes and saw her come out and start jogging towards the park. He was going to get her schedule down. She was back in exactly twenty-four minutes. He estimated two minutes to jog to the park, a twenty-minute run and another two minutes to jog home.

He smiled to himself as he got in the shower.

Later that morning Derek was standing in front of the OR board with Richard. As Mark walked up, the chief's pager went off and he left with a scowl.

Mark asked, "What's wrong with the chief?

"He's micromanaging the board. He's a junkie."

"Him? You're the one who looks all strung out. Late night with the lesbian?"

Derek laughed, "No, just a little tired. Leslie is fun. She has got some great real estate deals out there. Don't mention to anyone that she's gay."

Confused Mark asked, "Why not?"

"Meredith wants me to date before I start anything with her. Something about not being the rebound girl."

Mark laughed heartily, "Rebound shit! I've heard that before. Women are a little crazy. I guess that's why we love them. Glad to know you figured out how to get back on that horse. Aren't you cheating if you go out on a date with a lesbian?"

Derek chuckled and said, "Meredith doesn't need to know that and thanks dad for your advice."

Mark muttered, "Shit! Perky Sydney at 12 o'clock. See you man. I have your back with Meri."

Derek said, "Coward!" Derek watched as Mark jogged swiftly down the hall.

Sydney came up and said, "Dr. Shepherd."

"Dr. Herron."

"Here's a question for you. Were there actual shepherds in your lineage?"

"I'm sorry. What?"

"You know. Shepherds. The ones who watch over sheep. I mean in genealogy. My name for example. It's not really after the bird."

"Well, I…"

"Oh. That's okay. Maybe we can talk later. I know I've asked you before, but I'd love to buy you a drink and talk surgeries."

He smiled a little and said, "I could meet you at Joe's tonight after work for a drink."

"Really!" She was very surprised. She'd only asked him ten or twelve times already. Maybe he was ready to move on.

Derek said, "You know. I'm sorry, but I have a surgery I must get to now. See you later."

Sydney said, "Of course. I'll meet you at Joe's later."

Derek walked to the coffee cart to get an espresso before his surgery. He saw Meredith in the short line and walked up behind her and breathed her in.

She said without turning around, "Dr. Shepherd."

He laughed and asked, "How did you know it was me?"

She turned around said, "I have a very heightened sense of smell. And you're the only one who's bold enough to get in my personal space." If she had backed up an inch her ass would be in his groin. She glanced around. The only people in line were visitors, not any hospital staff.

"Is it a good smell? Something you could get used to? Something you could be around forever?"

She giggled and said, "You know for someone who was on a date last night you are being very forward. So, how was your date with…"

"Leslie. It was good. Lots of chatting."

Meredith scrunched up her nose. "You're chatty?"

He raised an eyebrow and asked, "You're not?"

She placed her order and laughed, "Not exactly." Derek got out money and paid for hers and ordered his.

"Thanks. You didn't need to do that."

"My pleasure Dr. Grey. You'll be happy to know I have another date tonight. With a different woman." He paid for his as they walked towards the elevator.

She grumbled and said, "Not wasting any time, are you?"

"Just following direction. Your direction. Are you always so bossy? Cause I am to please. And to pleasure you." He gave her a devilish wink.

She whipped around to say something to him just as a group of people walked up.

They waited for the elevator along with some other staff and Meredith couldn't give him a retort. She bristled as she hated not getting the last word in. They all got on and went about their day.

Callie and Addie were drinking at Joe's and watched as Sydney came in and grabbed a table for two. Soon afterward, they watched as Derek came in and sat down at her table.

Called asked shocked, "Derek and Sydney? This isn't bothering you?"

Addison said smugly, "No. She's been after him forever to have a drink. I'm guessing he is doing it to get her off his back." They watched as Derek went to the bar for drinks.

Callie asked concerned, "What about that girl last night? I mean he is really getting back out there Addison."

Addison replied nastily, "Must not have too well if he's here with Sydney tonight! I guessing that was the Mary Derek and Mark were talking about. But today I heard them talking about Mare. Sounds like a horse!" They watched as Derek went back to the table with drinks.

"So, Derek. Why the brain? Why biology's crown jewel? I'm a big fan of your work."

"You mean why did I go into neurosurgery?"

"Something must have stirred you as a youngster. Come on. Share. Share with Sydney."

Derek laughed and said, "It was the headset with the magnifying glasses that tipped the scale for me." He watched as Mark came into the bar and raise his eyebrow and snicker.

Sydney threw her head back and laughed. She said, "Says the man with a sense of humor! I like that. Yes, I do."

Callie watched Addison carefully watch their exchange. "Looks like the date is going pretty well. Are you sure you don't have a problem with this?"

Addison said firmly, "No, my problem is I'm in love with a man that's dating. And I don't care if he dates Sydney. It's the one he dates after Sydney that's a problem. If I had any sense…"

The bell dinged, and they looked up to see Grey and Yang enter the bar. Addison got a chill and the hairs on the back of her neck stood up. Derek catches Meredith's eye and winks.

Cristina snarled, "You snag a table and I'll get the drinks. God Izzie is getting on my last nerve. I'm glad she is stuck with that little kid in peds. I hope she's counting marbles out of his ass all night!"

Meredith laughed. Izzie and Cristina could not be more different. She liked them both even though they had nothing in common. Cristina was Meredith's dark side and Izzie was the bright and bubbly she wanted to be. Meredith grabbed a table in sight of Derek.

Sydney's pager went off and she said, "Oh. It's work. As if you didn't know. I'll just be a second okay."

Cristina sat down with the drinks and stared at Derek and watched Sydney walk away. "Shepherd is here with the queen of perkiness? She smiles more than Izzie." They watched as Mark made his way over to Derek's table.

Meredith said, "I think they are on a date. That's definitely a date, right?"

Cristina snarked out, "Maybe she's dying!" She clinked glasses with Meredith.

Mark sat down and asked trying to control himself, "Is she dying? Is that why?"

"Grow up. You were the one who said I should start seeing people. She's nice. She asked me out."

Mark said sincerely, "You want me to do a fake heart attack? I can do a great fake heart attack."

Derek shook his head. "Here she comes."

"Carry on." Mark got up and Sydney said, "Dr's. S & S together! Dr. Sloan. How are you this evening?"

Mark said, "Great." He headed back to the bar to watch. From that vantage point he could see Addison and Meredith watching discretely. He laughed loudly. He caught Derek's eye and patted his chest and mouthed heart attack.

Cristina watched Meredith closely and said, "You're being a little obvious Mer. I'm hurt that you aren't hanging on my every word."

"Um… What?"

Cristina hissed, "Is this why you dragged me here? So, you could watch McDreamy go on a date? That's just sad and pathetic. And if he's interested in her, I question his judgment. Maybe he has a brain tumor!"

Meredith said, "It's Sydney. In the movies when the handsome and sensitive football player kisses the awkward and freaky girl in front of the whole school…That girl was her."

Cristina said sincerely, "You are very awkward and freaky." Meredith rolled her eyes. Freaky watching the man you craved on a date.

Addison's phone rang, and she answered it. After a brief one-sided conversation, she hung up. "I have to go Callie. My brother Archer is having a mini crisis with my parents. I must make some calls and run interference."

"I understand. Do you want me to stay here and…"

"You don't need to. Trust me. Nothing is going on with Derek and Sydney. Zero chemistry. I think he's just trying to show me he's moving on."

Callie sipped her drink and said softy, "Maybe he is Addie."

Addison laughed and said confidently over her shoulder, "Not with her he isn't." She left the bar and Callie quickly followed.

Derek was trying to pay attention to what Sydney was saying. He really was. She was nice, but he kept glancing over at Meredith who he caught watching him a few times.

After a while Sydney turned around to see what was continuing to occupy Derek's eye and mind. It had to be the new intern Grey. Sydney had a healthy dose of self-confidence. Derek had never been interested in her before. Derek was charming and trying, but obviously he wasn't ready to move on with her. But maybe he was ready to move on with Grey. She thought, can't have enough friends and they could always talk surgeries. He was very talented.

Sydney reached across the table and squeezed Derek's hand.

She smiled and said "Derek."

A little alarmed Derek said hesitantly, "Sydney?"

Mark watched intently, ready to do the fake heart attack if things progressed much further.

"I want you to know that I'm really enjoying our date. But I don't think we should do this again."

"You don't?" He heaved a sigh of relief.

I'm a lot of woman. Ok? I bring home the bacon."

Derek smiled a little. "Ugh…" What does someone say to that?

"Fry it up in a pan, serve it with eggs or a sandwich or crumbled up on a Cobb salad."

Derek said lamely, "You do a lot with bacon."

"Not just bacon. But Derek, I bring a lot of things to the table. And I'm looking for a man who can do the same. A man who can meet my needs. All of my needs. I just don't think you're ready to move on with me. But I think you might be ready to move on with a certain someone." She glanced over her shoulder and then raised her eyebrow at Derek.

"Hmm. Well, you might be right. Thanks Sydney. I really did enjoy this and getting to know you better. If things were different or my feelings weren't already…. My treat tonight?"

Sydney stood up and said, "Good luck with her. She's a lucky girl. I won't let this affect our work if you won't." She put out her hand to shake his.

Derek smiled and shook her hand. "I won't. And thank you again Sydney."

Cristina said, "Okay. Dates over. Can I go home now?"

Meredith said, "Yes go. I'll get this."

Cristina stood up and "My treat next time."

"Okay. Thanks Cris. I do appreciate this."

Cris left and Meredith went up to the bar to pay their bill. Derek was right behind her.

"Apparently I'm not good at meeting needs and I don't bring that much to the table."

"I'm awkward and freaky."

Derek said, "Listen. That was two dates. Per your request. Do you want to…"

Meredith's phone rang and she glanced at it. "Crap! I gotta take this." She stepped away as Derek paid his bill.

Meredith came back and said, "I'm sorry Derek. I have to go and handle something immediately. See you tomorrow?"

"But…"

She said sincerely, "I'm sorry." He watched dejectedly as she bolted from the bar.

Mark walked up and put a hand on his shoulder. "Sucks to be the girl, doesn't it? Let me buy you a drink before we head home."

Derek said angrily, "This is not how I envisioned this night ending! With you!"