Disclaimer: I own nothing.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~Seven Years Later~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Logan had told her to meet him in the lobby at six thirty. At six twenty-five, Rory was sitting in the lobby. It was weird, she was actually nervous. It had been over seven years since they had been on a real date. What if he had changed? What if she had changed? She couldn't remember the last time she was this nervous before a date. She was starting to come up with an exit plan to chicken out on the date when she saw Logan walking across the lobby.

"Hey, have you been waiting long?" He asked as he kissed her on the cheek.

"No, not long." She replied.

"You look great." He said as he handed her a single rose. "We should get going." He said as he placed his hand on the small of her back and led her out of the hotel.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~Seven Years Later~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Once they got to the restaurant, Rory had started to relax. They had decided to keep the conversation lite. They weren't delving into their major issues yet. They had decided to talk about some of the things that had gone on in their lives since they had been apart.

"Let's play twenty questions." Rory said as she sipped her wine.

"Twenty is too many." Logan replied.

"Ok, how about 10?"

"Ok."

"How are you not married yet? I figured as soon as we broke up, your mom would have been sending every perfect society girl your way." Rory asked

"Don't think she didn't try." He replied with a smile.

"And…?"

"And…"

"Any of them come close to being the future Mrs. Huntzberger?"

"There was one."

"What was her name?"

"Charlie."

"How long ago?"

"About two years ago."

"Who broke up with whom?"

"I broke up with her."

"How long were you together?"

"A year."

"A year? That sounds pretty serious."

"Yeah."

"Why did you break-up?"

"We were together for a year. Everyone was looking for us to take the next step including her. I just didn't see myself taking that step with her."

"Why not?"

"Sorry, you are out of questions."

"What? That was 10."

"Nope, that was 11." Logan said with a smirk. "Do you want me to recap?"

"Yes."

"Ok. How about 10? Why aren't…"

"Wait a minute, how about 10 doesn't count."

"I think it does. The game started with 'let's play twenty questions."

"Damn you and your technicalities."

"Ok, my turn."

"Fine."

"Last serious relationship?"

"Three years ago.

"Name?"

"Michael."

"Journalist?"

"No."

"Did he work at the White House?"

"On the hill."

"Profession?"

"Lobbyist."

"How long did it last?"

"Six months"

"Who broke up with whom?"

"I broke up with him."

"Why?"

"Aren't we at ten?"

"Nope."

"Like you, we were getting to a point in our relationship where we should be getting serious and I wasn't ready to take that step."

"What do you mean by getting serious?"

"He wanted to move in together."

"And you didn't want to move in with him?"

"If I moved in with him, people would expect us to take our relationship to the next level and honestly, I never saw the next level with him."

"I get it." Logan replied.

They sat in an uncomfortable silence for a few moments. They were both holding something back, and they both knew it. They had left the restaurant and were walking down the beach back to the hotel.

"Did you know that Mitchum would make a point to see me every year at the correspondence dinner?" Rory said breaking the silence.

"No." Logan said surprised.

"It's funny. The first time we saw each other, we literally ran into each other at the bar. We had some uncomfortable small talk and he left. The next year, he made a point to come to my table and say hi. The following year we were sat at the same table. He stopped coming in 2012, I assume because of his health issues."

Logan was caught up in his thoughts. 2012; that was his first year attending the correspondence dinner. His father had told him that Huntzberger needed to be represented and he wasn't healthy enough to travel. He had seen Rory at the dinner, from across the room. He remembered that it looked like she was searching the room for someone that was missing. At the time he assumed that it was her date. The next thing he knew, she was with a group of people, giving that fake society smile with a glint of disappointment in her eye. Even though they hadn't spoken, he knew deep down he wasn't over her. No matter how hard he tried to move on, she still had a large piece of his heart.

"Hello. Did I lose you?" Rory asked, breaking him from his thoughts.

"I'm sorry, what did you say?" Logan replied.

"I was asking if it was weird that I missed him. I mean with my own rocky relationship with him, I thought it would be weird, but it wasn't."

"It's not weird. As rocky as our relationship was, I actually miss him. Believe it or not, he and I started to get along toward the end. One of the last conversations him and I had was about you. He had told me that I should look you up at the correspondence dinner and if I was lucky you would talk to me."

"Really?" Rory asked.

"Yeah, he said that you were good for me."

"You know, he told me that before. At your birthday dinner before you quit." Rory said with a laugh.

"I'm sorry I gave you that ultimatum. I was getting my life in order, was branching out on my own, no longer under my father's thumb. You were graduating college. We were both starting new chapters in our life and I just wanted to do it together."

"I get that Logan, and I would have loved to start the next chapter of my life with you, but I wasn't ready to start it as Mrs. Huntzberger. I needed to find out who the real Rory Gilmore was before I could be Mrs. Logan Huntzberger."

And with those words, it finally made sense to Logan. While he had finally found himself, breaking away from his father, making his own decisions, Rory was just starting. She was going from being Richard and Emily's granddaughter, Lorelei's daughter, Yale student, small town sweetheart to a complete unknown. She wanted to make it on her own, not has Mrs. Logan Huntzberger, wife to the heir of a major media empire. He had to respect her for that.

"That makes sense. I'm sorry that I was too busy thinking about what I wanted to realize that." He said as they approached her room.

"Well, this is me. I'll see you tomorrow?" Rory asked as they walked up to her room.

"Definitely." Logan said as gave her a quick kiss and left.