It had been a long day in the office. After the president's recent eulogy in Chicago, there was much to write about and much editing to be done. Rory was exhausted.

10:00 hit. Five hours after she was supposed to go home. She decided to call it a night and get back to work early the next morning. She packed up her things, locked up, and headed out.

There was a new bakery that recently opened up across the street. She decided to stop in for a coffee cake.

"Here you are," the woman said, handing her the pastry bag. "I hate to kick you out, but we're closing in a couple minutes."

"Oh, no worries. Thanks!"

She stepped out and gazed up at the sky and out to the city for a moment. That side of town looked gorgeous at night with how it was lit up. It was a summer night and the weather was perfect.

As she started walking down the sidewalk, she caught sight of a familiar face coming her way.

"…Dean?"

He snapped out of his trance and looked up at her, for the first time in five years.

"Rory…?" he managed a smile. "What are you doing here?"

"I was just checking out this new bakery. I heard they're supposed to have phenomenal coffee cakes, so I'll be testing that theory out when I get home."

"I mean, what are you doing here in Chicago? Do you live here now?"

"Oh no, just stationed here for a few weeks. I'm a reporter for President Obama and came here to report on his eulogy from the other day."

"You're a reporter for the president?! Rory, that's so cool!"

"Oh, I'm nothing more than a blogger," she smiled and looked down for a moment, trying to be modest. "What about you? What are you doing here?"

"Well, this is my hometown," he gave a friendly laugh.

"Ah, right."

"I'm just here for a week to visit some relatives," he continued. "It's been a while since I've been able to get away from Stars Hollow."

"Right, how are things going with you back in Stars Hollow?"

"Well, Taylor made me the assistant manager of Doose's Market last year. So I'm doing that while going to community college online. Still living with my folks, but the free rent is helping me save up to actually go to a university."

"Dean that's so great! I'm so happy you're finally going to college. You have so much potential and I'm excited to see where this takes you."

"Heh, thanks," he shyly shook his hair and looked down for a second. "You look good, Rory. I mean, you look happy. I'm glad that you're doing what you've always wanted."

"Me too. I am happy…" she paused. "And it was good to see you."

"Good to see you too. Well, I won't keep you. I'm sure you're itching to try that famous coffee cake, and I should get back before my grandmother starts to panic. No matter how old I get, she hates it when I'm out too late. I'll see you later, Rory."

"Okay, yeah. Wouldn't wanna keep Grandma waiting. See ya…"

They both turned and slowly started walking away. In the spur of the moment, Rory spun back around and called out to him.

"Dean!"

He stopped and turned. "Yeah?"

"Why did you leave?"

"Leave? What are you talking about?"

"Five years ago, outside my grandparents' house. The last time I saw you. Why did you leave?"

He was silent for a moment, before slowly walking back up to her.

"I left because I didn't belong in your life anymore. Remember?"

"Yes, but why? We were still the same people and were doing fine right before that moment. What changed?"

"We weren't the same people, Rory. I had just gotten out of a marriage and my whole life had fallen apart. I needed to focus on getting myself together. And college changed you. Not saying that's a bad thing, I mean, it would be expected that you'd change after a drastic shift in lifestyle. But I didn't belong there anymore, in your new life. You were in college, ready to do big things like what you're doing now, and I was miles away working at a grocery store, trying to put my life back together. And then seeing you come out of your grandparents' house with all those rich college kids… it was just the last straw for me. I couldn't deny it anymore. You were going off on your own path and I wasn't gonna hold you back."

"Dean… I'm sorry…" she was stuck in place. "I didn't realize…"

He walked up and put a hand on her shoulder. "Hey. It's okay. It was my decision. I was angry and bitter about it for a long time, but I let go of it a long time ago. And seeing you here, now, as a reporter for the president… I know I made the right choice."

"But what about you? Are you happy?"

He sighed and looked away. "I'm happy about where my life is leading. I'm excited about what's in store for me. But…" there was a pause. "There's never a day that I don't miss you."

She was silent and kept staring at him.

"But it's all right. I've gotta get over it eventually, right?" he looked back at her. "I'm sure you have. I wouldn't doubt that you've seen other people."

"I uh…" her eyes met the ground again. "I was almost engaged to someone a couple years ago. But I decided to choose my career over marriage. Haven't seen him since then."

He looked deeply into her eyes. "You made that decision because you wanted the freedom to go your own way and have the career you wanted. And you got it. You didn't let someone else hold you back. That's why I left. You deserved better."

He had the most loving, yet sorrowful look in his eyes. She held his gaze for a few moments and without thinking, moved in for a quick kiss.

"Oh my gosh," she pulled away and took a few steps back. "I'm so sorry! I didn't mean for…" she kept moving back, turning red in the face.

"Rory…"

"Why do I always do this? Every time I see you, I just get so weird and can't think…"

"Rory calm down. It's okay."

"It's not okay! It's not fair to you. I guess I… I guess I've never completely gotten over you either. I never realize that until I see you again. Then I get all… well, you know…"

Dean remained calm. "You have a lot of work to do for your job. I have school and a whole new life ahead of me. We should focus on those things and see where we both are by then. And then later on… maybe we can take it from there."

"You want to give me another chance? After so many times of screwing it up?"

"I'm just saying we can see what happens. If we both feel the same way by then and are in a place where it's possible… we can give it a try."

She looked him lovingly in the eyes. "Do you promise to wait for me?"

He leaned down and kissed her cheek. "Only if you promise to wait for me."

They held each other's eyes for a few more moments without speaking.

"I'll let you get to that coffee cake," Dean finally said. "Bye, Rory."

A/N: My first Gilmore Girls fic ever. Definitely not my best work, but it was pretty effortless tbh. Gilmore Girls is just too brilliant and my skills aren't up to that level lol. I can't compete with it. But I just love Dean so much :L well, pre-Lindsey Dean lol. Anyways. Feedback welcome.