2019

He was sitting on Rory's couch in her appartment in Queens. The last almost two years it became a familiar place to him. He looked around. Emma was making some shaky steps at the coffee table and from time to time she looked at him and made her cute laughing face, where she squealed and her eyes became like slots. He smiled at her. "Good job!"
This morning he went to the supermarket with her, buying some groceries and diapers, because Rory had an interview with a local radio station. Due to her book release six months ago, she got some contacts and was now partnering the "Help Your Mommas Out" foundation, where they supported single mothers, to provide a safe and secure place for them and their children, to encourage and inspire them to be better women, mothers and community leaders. Rory loved every minute of it.
When he was standing in line at the checkout, Emma was sitting in the shopping cart and desperately wanted to keep the coffee creamer in her chubby hands, bursting out in tears when Jess tried to take it away from her to place it on the cash register. "S'okay sweetie, keep it. I know the code by heart", the blonde cashier winked at her.
"Thanks, you made my day", Jess sighed and put the other stuff out of his cart.
"No problem. Your daughter looks like an angel!" She smiled. "$28,75."

He didn't correct people anymore, he got tired of it. And he couldn't blame them, they looked like a family. When it was the three of them, he still felt a bit uncomfortable when someone assumed him to be the father in front of Rory, not sure if she's okay with it. But she also decided to just smile slightly and keep it like that.
Truth is, he was ready to be a family. They met almost every weekend alone or with some friends, had some business and coffee dates during the week, driving together to Stars Hollow last month to celebrate Christmas, where he overheard a curious Lorelai, who was interrogating Rory if there's something between them or not. He almost could hear Rory blushing, although she was out of his sight, stuttering that they're just friends and he's doing a lot for her and Emma. Jess heard the nervousness and the trembling of her voice and that alone gave him hope: it's not over.
He wasn't pining or he wasn't doing all of this just to get something. He really did because he cared for her and the kid. And he made a pact to himself that this time, it wasn't him who made the first step. He gave her so many opportunities in the past, now it's her turn. Both of them couldn't deny that there was still a connection between them, some electrical voltage. They were friendly, there was sometimes a playful banter, and some nights, when he was laying in bed, he heard her sweet voice from the wedding echoing in his head, telling him she never met someone else who understood her as well as he did. There was this drunken night, on Rory's birthday last October, some months ago, when they've all stayed in Bushwick, Jess, Rory, Matt, Eva and Todd. Lorelai was taking care of Emma, giving Rory a free night out. Tipsy and happy, she wanted to take an uber back home, but Jess refused to let her go.
"This time you'll stay with me here. S'too late already."
"Oh, is that your pick up line?", she asked and giggled, but gave in and followed him.
"No, no, no. My pick up lines are more tricky. More contentious." He grinned.
"Give me one! Pretend I'm one of these edgy hipster girls you like, with their ripped jeans and gym bags and dyed hair."
He let out a husky laugh. "You're a crazy woman."
"Jess, please!" She grabbed his arm and tried to punch him.
"But you have to promise to keep your hands off of me. Just a warning. I'm a pro." She stuck out her tongue in response.
"Well, firstly I would lean over to her...", he pushed Rory gently to the housewall, "then I'd give her an intense look in the eyes..", he licked his lips and came closer, "and then I'd ask her... is your daddy a baker? Because you've got some nice buns!"
Rory stared at him, with soft knees, but when his last words reached her brain and she saw his sassy grin, she slapped him with her purse and started laughing. "You're awful!"
"I just did what you desired. But hey, the pushing and staring part was quite okay, huh?"
Even in the dark surrounding, he saw her blushing and couldn't hold back a grin. Yup, still working.
Back in his appartment, he brushed his teeth and placed himself on the couch, watching Rory who was dressed in one of his shirts, due to the fact she didn't plan to sleep over. He sighed. He gotta stop having inappropriate thoughts or he'd need an extra cold shower.
Rory smiled shyly. "G'Night. Thanks for your... bed." She swallowed and her face got red.
He smiled in return. "Anytime. Night, Ror."
One day she will be ready.

Jess shook his head as if he wanted to get rid of these memories. He heard keys and soon after he saw Rory entering her living room. She smiled at them. "Hey, you two. How are you doing?"
"Ma-ma!", Emma squealed and hugged her leg, "Hey baby, I've missed you." She placed a kiss on her head.
"We're fine. Did some grocery shopping, she slept for an hour and a half, I was able to make two important phone calls and there's a casserolle in your oven."
She stared at him. "How are you doing this? Being superman?" Rory went to the kitchen and was about to make coffee.
"I'd prefer batman, but yeah..", he smiled and watched Emma, who was doing some acrobatics at the coffee table. The little girl turned around, smiled brightly, pointed out to him and simply stated: "Da-da."
He froze. Again, she grinned and walked towards him. "Da-da!"
"Uh, um, well, it's Jess, Em, we have to practice this again." He pinched her in the cheek.
"Jess." He looked up and saw Rory staring at him. "Yeah?" Suddenly the air felt thick and hot.
She came some steps closer. Slowly he got up, not disconnecting her eyes. Her lips shivered and she cupped his head in both of her hands. "I want us. You. me. As in in a couple. As in... a family."
His heart was beating so fast, he heard it pumping, running, screaming. He opened his mouth, but no words could escape from it. Instead he leaned a bit over, finding himself lost in a blue ocean, waiting for a response, not forcing anything. A second later he could feel her sweet lips again, fervently kissing him, new and yet familiar. Jess pushed her closer to him, groaning into her open mouth, sucking her bottom lip. With a last hard kiss on the lips he remembered there's still a toddler with them and he stepped away. Rory's eyes were brighter than ever, she smiled and he loved to see her rosy cheeks.
"Finally." He smirked.
"Yeah, finally. You know I... I love you."
He tried hard not to gasp, his ears ringing. Those words out of her mouth, not just in his imagination, made him dizzy and happy, all at once. He took her hand, squeezing it. "Never stopped loving you."

He felt a tiny hand pulling on his shirt. "Da-da!" Emma lifted her arms in order to be picked up by him.
"C'mon pumpkin. Maybe you're ready for a second nap. Dada really needs some quality time with Mommy now."

A./N.: Thanks again for your sweet reviews and suggestions. Hope you like the descriptions of this event in 2019 ;)
The chapter of 2029 gives you already a glimpse of it. Enjoy reading!