Author's Note: Here's my headcanon for the future of the Gilmore clan. Dedicated to my friend Rachel in hopes that it will make her feel better.
The Next Adventure
"I want to do it right this time."
Lorelai listened to Logan's voice over the phone and smiled. "I gotta say, I was not crazy about the way you did it last time. Actually, I really wasn't crazy about how you handled the after-part."
"I know. I overreacted. I regretted it as soon as it happened. But she was right. We all know she was. She had her whole life ahead of her. Nothing holding her back from what she was about to do, whatever it was. She deserved to be free from any ties, and that included me. I was set. California was amazing, and I don't regret going, and I don't really regret that Rory didn't come with me. But it's been six years since then. Everything is different now. The only thing that hasn't changed is the fact that I know that she's the woman I want to spend the rest of my life with. Lorelai, I love your daughter with all my heart, and I'd like to ask again for your blessing to ask her to marry me."
It took Lorelai a moment to think everything through. She felt a tug on her shirt. "Will, Mommy's on the phone, sweetie," she whispered to her three year old son. "Logan, if she says yes, I'll be really happy for you guys. But if she says no, don't you dare break her heart again. You weren't there when she had to pack up the love rocket."
"I know. But in going through all that, look what Rory did! She's a senior White House reporter for the Washington Post. And I got to go to California, build a tech company, sell it in three years for a fifty million dollar profit, and start my new life as a tech lobbyist. It brought us back together, better than ever. And I hope she says yes. But if she doesn't, I'm not going to leave. I won't ever leave unless she tells me to go," Logan assured her. He was wandering around Dupont Circle, and his fingers were starting to become a bit numb in the early spring air of D.C.
"You've got my blessing, Logan. And Luke's. He's not here right now, but anyone who can convince our son to wear a tie without an hour's worth of fighting is welcome in the family."
Logan grinned at the memory of taking Luke and Lorelai's son into the foyer of the Gilmore mansion in Hartford and explaining how a boy in a tie is a superhero. From then on, Will Danes loved wearing a tie. He would always tell his mother, "Long ties are for superheroes like Logan and bowties are for kings like Grandpa." Will's tie choice depended on whether he wanted to be superhero or a king that day. Though the tie was usually paired with a backwards baseball cap. Like father, like son.
Lorelai and Logan said their goodbyes and hung up the phone. Lorelai gave her son the attention he was looking for, and Logan made his way back to the apartment that he and Rory had shared for the past year.
Three hours later, the phone rang at the Gilmore home. The maid answered it. "Gilmore residence."
Rory was out of breath and far too excited to form proper sentences. "I need to talk to Grandma and Grandpa!"
"Pardon me?" the confused maid asked.
"Emily and Richard are my grandparents. Can you get one of them please?"
"Mr. and Mrs. Gilmore are dancing at the moment. If you'll hold for a moment, I'll get them."
Logan saw Rory's excited expression turn to a frown. "Everything okay?"
"The maid said they were dancing."
"Well they do dance, right? We've all seen them dance."
"Yeah, but at events and stuff. Can you really picture my grandparents just dancing at home?" she asked, her eyebrows raised dubiously.
Logan shrugged. "I dunno, maybe. Richard does some strange things sometimes. And depending on her mood, Emily might go along with it. Ask when you talk to them."
"I will," Rory replied with a nod.
"Hello, Rory?" Emily's voice came through the phone. She sounded a little out of breath herself.
"Grandma, were you guys dancing?" she asked.
Emily rolled her eyes. Sometimes Rory was far too much like her mother. Distracted from her purpose by whatever strange thing crossed her path. "Yes, we were. At his last checkup, the doctor told your grandfather that he needed more cardio exercise. And golf is not a cardio sport. So we've started spending a half hour dancing before dinner a few times a week, and another half hour after dinner when we can. And I must say, it's quite fun. We were nearly finished when the phone rang. Did you call for a reason, or are you just checking up on our evening activities?"
Rory was reminded of her purpose. She looked down at the pear-shaped diamond on her left hand. "I was wondering if you'd be able to host an engagement party later this month."
"An engagement party?" Emily asked, trying not to read too much into the request, but becoming increasingly excited.
"Logan proposed, and I said yes, and we're getting married!"
"Oh, Rory, this is the most wonderful news!" Emily gushed. "Let me get your grandfather. You should tell him yourself." She placed the phone down on the table and shouted for her husband. "Richard! Richard, come speak to Rory!"
It took Richard a minute to join his wife in the dining room. He had been pouring them each a brandy to share before bed, as they often did after their dances. He picked up the phone, eager to speak to his granddaughter. "Hello, Rory! It's lovely to hear from you. How are you?"
"I'm great, Grandpa! Logan and I are engaged!" she announced. The more she said it, the more excited she got. She had Skyped her mother as soon as it happened. Lorelai had been waiting for her call. And they had mostly just screamed and laughed in excitement. Her second call had been to Lane, though that had been cut short because Steve had apparently put gum in Kwan's hair and Zach was trying to cut it out. The third call was to Paris, who had immediately asked when the engagement party was and where they were registered. That had prompted the need to call Richard and Emily. Normally, Rory wouldn't have called them so late in the evening; it was rude to call for a non-emergent purpose after eight. But now that she'd done it, Rory was excited to share the news with as many people as possible.
Richard took in what Rory told him and grinned widely. "Oh Rory, I'm so happy for you. I have no doubt that you and Logan will be very happy together for many years to come. The perfect D.C. power couple."
"Yeah, I guess we are," Rory replied with a laugh.
"Oh, Rory, it looks like your grandmother needs to speak with you. She's got her planner out. I'll give the phone back to her. Congratulations, Rory, and please pass my sentiments along to your fiancé."
Emily snatched the phone out of his hand. "Alright, I've got a few weekends open for you to choose from."
Rory grabbed a pen and her notepad and started scribbling as her grandmother gave her instructions and options and enough information to make an unexperienced person's head spin. Rory was not so naïve. She knew what to expect, and she had already thought of a lot of it on her own.
As his fiancée wrote notes and discussed various plans with her grandmother, Logan sat back on their sofa and watched with a smile on his face. He was honestly a little surprised she had said yes. But he was overjoyed. When he was twenty-three and had proposed the first time, he never thought he could love anyone more than he loved Rory. She was the end-all and be-all for him. But in their years apart, he had grown wiser. He had been young and impetuous with her the first time. His heart ruled his head, something he thought Rory loved about him. Now, his age and experience had tamed him. He saw Rory's ambition and drive and focus not as something endearing and cute, but as a valuable set of traits. Her absence had taught him as much as her presence had. Since he had come to D.C. three years earlier, they had grown together. Their newfound friendship reopened the love they once shared. It was different now; better and stronger and deeper. This would last. This would be the beginning of their life together as a team and as a family. And he couldn't wait to start this new chapter with Rory Gilmore.
Logan stood up and took the small whiteboard off the wall. They used it to write notes to each other, thanks to the irregular hours that a reporter and a lobbyist tended to keep. He erased his note reminding her of their dinner plans, and drew a picture on it. When he finished, he held it up.
Rory noticed his movement from the corner of her eye. She looked up and saw Logan holding up the whiteboard with a heart drawn on it. She smiled. Rory knew she had made the right choice. She had made the right choice in taking a chance on Logan when they were at Yale. She had made the right choice when she had turned down his proposal at her graduation. And she had certainly made the right choice in agreeing to marry him now. Six years before, she was headed out on an adventure that she had to face alone. Now, they would face all their future adventures together, and she couldn't wait.