Disclaimer: I own a couple of minor characters you'll see, but that's it. Jess, Rory, and the rest of the regulars are definitely not mine.

A/N: BLAME ADELE. This new story is completely because her new album is incredible and inspired a short story from me. The timeline will go from 2008-Present. Just hang with me ;)

THANK YOU FOR THE REVIEWS! :)

Chapter Rating: R

I would never lie to you unless you tell me to
Every part of me, all my words to hold
And hold against me, why won't you let it be?

September 3, 2015 at 8:30 p.m.

His hands fumbled with the doorknob behind Rory's back and he grinned against her lips at her reluctance to help him get it unlocked. He pulled back from her eager mouth and breathlessly chuckled as he gently moved her aside.

"The quicker I get this unlocked, the quicker we can get out of our clothes," he whispered against her ear, earning a visible shiver from her, before skillfully unlocking the door and pushing it open.

She bit her lip with a playful grin and stepped inside the dark house with him, jumping up slightly and wrapping her legs around his waist. He caught her gracefully and laughed, pressing her against the counter to get a good grip on her body. Once he hoisted her bottom onto the cold countertop, she hurriedly unbuttoned the shirt underneath his suit jacket and shoved the coat onto the ground, her mouth glued to his.

"Jess," Rory gasped, raking her nails against his scalp as his lips traveled down her neck, his tongue pressing against her pulse.

"Come on," he mumbled, lifting her to take her to the bedroom. She shook her head and moved her hands to his shoulders, clutching tightly.

"No," she said, shaking her head as she did. "Stay here. It's exciting," she said with a laugh as he sat her bottom back on the table and reached around to unzip her dress with a boyish smirk. He leaned back and let his eyes roam her body as he pushed the dress down her shoulders.

She squirmed under his gaze, blushing furiously as his eyes finally met hers. "Well, like what you see?" She teased, trying her damnedest to be as confident as he was in these situations. It just wasn't her. She barely liked to be naked with the lights on.

Jess chuckled as he raised an eyebrow at her statement. He leaned closer, placing his hands on her cheeks, a smirk playing on his lips. "Oh I do," he said, quietly, "You're the most beautiful woman I have ever seen."

"Stop, you're embarrassing me," Rory laughed, leaning in to kiss him again though her face was fully flushed from his compliment. She wrapped her arms around his neck and pulled him close, her teeth lightly scraping against his bottom lip. Without a second thought, she pushed his pants down with her feet and wrapped her legs around his waist.

Jess pushed up the fabric at her thighs and pressed into her as his fingers dug into her thighs. "Shit," he breathed out, feeling her warmth as his mouth moved from her mouth, to her neck, to the swell of her breasts. His tongue ran down her breasts and earned a satisfied moan from her mouth.

September 4, 2015 at 12:10 a.m.

After a deep breath, Rory turned on her side and looked over at Jess. She held her head up with her palm and looked down at him. "Now that we've successfully avoided the conversation—"

"Three times," Jess said with a smile as he opened his eyes and looked up at her. "Once on the counter," he said, lifting up and kissing her gently, "once in the shower." His lips pressed against her chin and down to her neck. "And once again when we hit the bed. Want to make it four?"

She laughed and tucked the sheet closer to her body, closing her eyes as she tilted her head to the side. "No," she said, though her body said otherwise. "We have to talk about this."

With a sigh, Jess conceded and pressed his head back against the pillow behind him. "What do you want me to do, Ror?"

"I don't know," Rory said, honestly, looking back at him. She placed her hand on his cheek and looked down at him. "I was caught off guard. I am so proud of you, and I support any business decision that enhances your career. I just thought we'd be closer to figuring out how to be closer."

"Rory, this is just the start in expanding Truncheon," Jess began, sitting up and leaning back against the headboard of the bed. "The next one we open is going to be wherever you are. That was always my plan." He paused and ran a hand through her hair, "I probably should have included you in that discussion. But, you've got to give me a break, I've been alone for a long time and I have never had to discuss my future with anyone else."

A weak smile graced her features as she leaned into his hand with a deep sigh. "I'm sorry I overreacted. This is still new to both of us and I just thought that maybe—"

"I was going to propose," he interjected with a grin as he looked up at her. "I didn't know you were ready for that."

"Are you?" Rory asked with a nervous laugh pushing her hair behind her ear. "I mean, I can understand if you aren't. It hasn't even been a year yet, and we live far apart—we barely see each other."

"I've been ready since I danced with you at Luke's wedding," Jess responded seriously, staring back into her oceanic eyes. "You've always been it for me."

Her heartbeat increased and she stared back at him for a moment before leaning in and kissing him again, pressing her hand against his jaw. She leaned back after a moment and gave him a small smile, pressing her forehead against his.

"I'm ready, too," she said, quietly.

September 4, 2015 at 12:31 p.m.

"So you're… engaged?" Lorelai asked with an unsure smile, taking a sip of her coffee as she leaned against the front desk of the inn, holding the phone between her shoulder and her ear.

"I don't know!" Rory exclaimed, looking down at her coffee as she waited on her toast in the toaster. "We really didn't talk the rest of the night and then I didn't want to bring it up this morning before he left."

"You both said you were ready to be engaged, and that was the end of it?" Lorelai asked her, tilting her head to the side with a confused chuckle.

"I guess so," the younger Gilmore said with a shrug as she took a long sip from the large ceramic mug in her hand. "Maybe I just shouldn't mention it until he does. Maybe he said it in the heat of the moment."

"Yeah," Lorelai said slowly, laughing a little as she set her mug down. "I think that's probably not the best way to handle it. Just ask him. Is he coming back tonight or are you going there?"

"I'm driving there for the weekend," Rory said, leaning back against the kitchen counter in the break room of her office. "I guess we will talk about it then."

"Hon, are you sure you want to get married?" Lorelai asked with a smile.

"Do you not want me to?"

"Oh no, no," Lorelai said, shaking her head as she set down her decorative mug. "Of course I want whatever you want. I just want to make sure you are really sure about this."

On her way back to her office, she stayed silent. As soon as she was sitting behind her desk, the picture beside her laptop caught her eye. She smiled as she took in the image. A candid shot in front of her mom's Christmas tree, her arms around Jess' neck from behind as he opened the gift she carefully picked out for him. His smile was so childlike, full of excitement. And she could just remember how happy she was to put that smile on his face.

"Oh, I'm sure," she breathed into the phone with a small laugh. "I'm so sure."

She could hear her daughter's smile from the other end of the line and she nodded, taking a deep breath. "Then you definitely need to talk to him, kid," she said with a grin.

December 23, 2015 at 10:57 p.m.

"I'm scared he won't like his gift," Rory stated, her eyes on the ceiling above them. "And then he won't like me."

"You've been around Jake over a year, Rory," Jess mumbled, his head stuffed in his pillow as he tried to sleep. "He already likes you."

"No," Rory said, lifting up in bed to look over at him. "No, this is my first Christmas living here and I want him to like me living here as his mother. If this gift isn't up to par then I'm not good enough."

"Well," Jess said with an agitated sigh as he sat up in bed as well. "Seeing as last Christmas he got half of my steak from dinner and a tennis ball, you're already winning."

"You're an awful parent," Rory said, gaping at him. "Look, this is important. It took Paul Anka quite a bit of time before he liked me. I just need Jake to warm up a little faster."

"Okay," Jess said with a smile as leaned forward and pressed his lips to her forehead. "For starters, you should know, you are sleeping in his spot every night now. He was forgiving when it was every other weekend, but every night? I don't know how well he's handling it."

"Oh my gosh! I've booted him out of his bed!" Rory screeched, getting out of bed and running to the door. "Jake!" She called after she opened the door. "Come here, boy!"

Jess laughed out loud and fell back into the bed with a groan. "Rory, come on... it's going to be an early morning for us." He heard the tapping of nails against the hardwood floor as the jingling collar came closer. Without another second passing, he felt the bed sink down as his large Goldendoodle bounded on the bed and pawed his face.

"He's sleeping with us," Rory said with a smile as she walked over to him and jumped in the bed next to them. "Now he'll definitely love me."

"Not more than I do," Jess said with a grin as he scratched behind Jake's ears and looked over to Rory. He pulled her closer and let his hand slide up to hers, taking it gently as he glanced at the diamond on her hand. "This looks great on you."

With a content sigh, Rory leaned back into him and gazed down at the diamond. She felt Jake settle at their feet and Jess' arms wrap around her torso. "I think so, too."

"Now it's time to go to bed," Jess said with a smirk as he slowly closed his eyes.