Story Title: This Time Around

Summary: You never forget your first love. They stay with you long after you have moved on. What if you were given a chance to do things right? Set a few months after the finale.

Pairing: Rory/Dean

Disclaimer: I do not own Gilmore Girls. It belongs to Daniel and Amy Sherman Paladino. What I do own is the concept for this story, so please don't use it without my permission.

AN: Just a quick note: I am basing Dean's look on the way he looks now because my dad and I are semi-obsessed with the show Supernatural. I've watched it from the beginning and Jared Padalecki's hair gets longer and more Fabio-like with every season. lol And do you want to know something else that's funny? I'm a Dean girl when it comes to that show too. Ay yi yi

After a long summer and fall spent following who was now the President of the United States Rory had made her way back home. Not necessarily to her mom's but to Stars Hollow. She had missed it more than she had thought was possible. It hadn't taken her long to find a house for rent. She'd mentioned to Miss Patty that she was looking for a place and by the end of the day Miss Patty had found her five places to look at. The woman really did have her finger on the pulse of the town, nothing got by her.

She lived close enough to her mom that Lorelai would pass her house every morning on her way to work. She lived across the street from Lane and Zack which made things even better. She was starting to adjust to things when one fateful trip to Doosey's changed her life for the better.

She was grabbing a few things that she'd forgotten when she came in earlier in the day. The only reason she was making Thanksgiving dinner was so that Luke didn't have to. She was trying to decide between mini or jumbo marshmallows when someone's arm reached past her from behind. The person apologized and her breath caught in her throat. Her head swiveled slowly to look over her right shoulder.

His hair was so long that it covered his ears and fell in his eyes but she would know those dark eyes anywhere. She had thought that she would never see him again. The last she'd heard he had moved back to Chicago.

"Hi," he said shakily.

"Hey," she said, the air being sucked out of her again.

"I should probably move, maybe then you won't look like a frightened baby deer," he said with a sigh.

"I'm sorry," she said quickly.

"It's okay. Stars Hollow is pretty small; we were bound to run into each other eventually," he said, shoving his hair out of his face.

"Dean?" A young girl called from the end of the aisle.

Clara had to be at least nineteen now. She had grown up to be really beautiful with her shoulder length blond hair and long legs. She wasn't as tall as Dean but she almost was. Dean started to walk away but Rory put a hand on his arm. He looked down at her hand before meeting her eyes.

"We're both adults. There's no rule that says that we can't be friends," she said reaching into her purse for a pen and a piece of paper.

She found a post-it pad embossed with Hello Kitty and a red glitter gel pen. Her mom had purse bombed her again. She sighed mutedly as she scribbled her number onto a post-it then tore it off the stack. Dean shook his head with a laugh. He took the pad and pen from her and quickly jotted his number down.

"I'll only give this to you if you promise to call me," he said.

"I promise," she said with a nod.

"See you around Rory," he said with an easy smile.

That smile had threatened to melt her heart as a teenager. Her heart skipped a beat as she watched him walk away. She grabbed a bag of mini and a a bag of jumbo marshmallows without looking. She would be on the safe side and she'd have something to snack on; it was a win/win.

XXXX

Rory had shown up at the Inn half an hour early so that she would avoid her mom. She had promised her mom that she would help decorate the bedrooms for the holidays since three of the maids were on maternity leave. She was draping holly over a gas fire place mantel when someone knocked on the door. A few seconds later Lorelai stepped in.

"Hey," Rory said over her shoulder.

"Hey. I thought that we could get something to eat before you started."

"I didn't realize that you wanted to," she said apologetically.

"It's my fault. I should have mentioned it. Sookie's talking about trashing a ginger bread house because the gumdrops are clashing with the frosting design. How about we save it?" Lorelai asked hopefully.

"Sure," Rory said, going back to what she was doing.

"Come and see me before you leave?"

"Okay."

Lorelai left the room, closing the door quietly behind her. Something was off, she could sense it. Alarms went off in her head when Rory not only wouldn't meet her eyes but she didn't stop what she was doing. A busy Rory was a Rory who had something to hide.

Rory made her way downstairs an hour and a half later. She went into the kitchen to find Sookie in the middle of yet another crisis. Sookie had cut her arm just above her elbow. One of the servers got her to sit down before wrapping a towel around Sookie's arm. She was definitely going to need stitches.

"Hey Peaches, I packed up your half of the house, it's on the counter," Sookie called over the noise.

"Thanks. Can you tell my mom that I'm taking off. I've got plans with Lane tonight."

"Sure thing, have fun."

Rory grabbed the container and booked it down the hall, past the check in desk and out the door in less than a minute and a half. If her mom had seen her than she hadn't tried to stop her. She slumped against her seat trying to slow down her racing heart. She didn't like keeping things from her mom but she kew her mom would have something against her talking to Dean. She was an adult and she didn't have to tell her mom everything.

XXXX

Lorelai put her feelings about Rory aside after she left work. She had an appointment with a flower vender that Sookie had recommended. She had hoped that Rory would come with her but she understood that Rory had a life of her own. Rory had gone with her to every dress fitting. She had decided to use the dress that she had found when she and Luke were first engaged. The dress couldn't be more perfect even if she would be wearing a white wool coat over it. Nothing would stop her from getting married in the gazebo.

She wanted simple flowers, maybe Christmas hostas or white orchids with red poinsettias along the aisle since they would be getting married on New Years Eve. Luke had taken her by surprise by giving her her engagement ring back and announcing that he still wanted to get married.

Her life hadn't been the same when they weren't together. She had been lying to herself when she thought that Christopher would ever take to living in a small town. Her whole life was there and she couldn't uproot it.

She had put her hurt feelings about being lied to about April aside. After thinking about it, she realized where Luke was coming from. Learning that you had a daughter who was kept from you for twelve years is a big shock. Lorelai liked April, she was a good kid who was luckily nothing like her dad. She'd had a partner in crime when she decided to gang up on Luke when Rory wasn't there. Honestly, April reminded her of a more chatty version of Rory.

Luke had moved in with her and turned the room over the diner into an office. He was still getting used to the change and Lorelai was patient with him. It was hard breaking certain habits that you'd had for most of your adult life. Things were getting better every day.

Lorelai wasn't used to Rory keeping secrets. If Rory was keeping something from her it was more than likely something that she wouldn't approve of or it was about a guy. She just prayed that it wasn't both because with Rory that was usually the case.

XXXX

Rory was going over an article that she would be sending to the New Yorker when her phone rang. She picked her phone up to see Dean's name staring back at her. She pressed the answer button and saved her work at the same time. It wasn't due for a couple of days anyway.

"Hello?"

"Hey."

"Hey yourself," she said with a smile.

"You're up late."

"So are you," she countered.

"I was going over some blue prints."

"Are you working with Tom again?"

"Sometimes. I design houses," he admitted.

"Wow, that's great," she said in surprise.

"Yeah, my parents are really proud. The four years of architectural school they helped pay for are paying off," he said with a light laugh.

"You decided that college was for you after all?"

"Yeah. I realized that I had an eye for architecture not long after we stopped seeing each other last. My parents talked me into moving back to Chicago for school and I moved back a couple of months ago," he explained.

"I'm really proud of you."

"Thanks. I'd ask what you've been up to but everybody here seems to know. Babette told me you were on the campaign trail with Obama."

"Yeah. It was surreal. I found myself doubting if it was really happening half the time."

"I thought you wanted to be the next Diane Sawyer."

"Even Diane Sawyer had to start somewhere."

They talked for a few minutes longer before he had to get off the phone. She was glad that he'd called. She had been thinking about him a lot since she had run into him the day before. The feelings that she had for him were slowly coming back without her realizing it. She was reluctant to start a relationship with him since they had both played a role in the demise of their relationship. They were going to have to set some boundaries and guidelines if they were to start dating again.

XXXX

It had been three days since Rory had seen her mom. Avoiding her had been easy since her mom was a creature of habit and rarely varied from her morning routine. Rory had taken to working late and sleeping in, giving her mom plenty of time to leave Luke's and be at work before heading out. She couldn't keep this up forever, her mom was bound to grow tired of being ignored eventually.

Her luck finally ran out that weekend. Her mom had shown up at her house with breakfast and Rory knew that it was time to tell her the truth. They ate in the kitchen since the couch and coffee table were overflowing with her work.

"You've met someone, haven't you?" Lorealie asked.

"I ran into someone, Dean," Rory admitted with a nod.

"I've seen him around town but I thought that he wasn't staying," Lorelai admitted.

"He's back to stay. He went away for college and now he's starting his own business. He's really matured since you saw him last."

"He's also in dire need of a haircut, he's starting to look like the Shaggy Dog."

"I was thinking Jesus, but you always have to take it one step farther," Rory said with a shy smile.

"So, what does he do?"

"He's an architect, he designs houses."

"Are you two..."

"We're just talking right now. Thanks for the post-its and pen by the way."

Lorelai grinned evilly before taking a sip of coffee. She had trouble trusting Rory's judgment when it came to guys since Jess. Even Dean had failed her when he had cheated on his now ex-wife with Rory. She had been worried about her after everything that had happened with Logan. She hoped that Rory would be smarter this time around.

AN2: Sorry this is so short but this is a new couple for me to write even though Dean was my favorite of all of Rory's boyfriends. I hope I got at least one person's attention. Let me know what you guys think.