2023 - Winter

"Crap." A voice came out of her kitchen followed by a clanging sound. Emily opened carefully the door and saw Jess standing at the sink, a baby bottle at the floor and some liquids all over the work plate.
"Need help?" she offered. He turned around with a startled expression but relaxed after seeing her. "No, thanks. Sorry for the noise. I was just about to clean Rick's bottle and then, yeah..." he explained and continued to clean up his mess. "Well, if you like, join me for a drink in the living room. You might want something different than milk" she smirked and left the room. Jess bit his lip. Never in his wildest dreams he thought that Emily Gilmore would invite him for a drink. He dried the table and went after her.

"Cheers!" she stated and clinked glasses with him. He nodded and took a sip. It was quiet in the house, everyone else was sleeping. Some candles were still burning and added to a cozy atmosphere. "How different to the majestic house they've owned in Hartford", he pondered.
"So Jess, quite some things changed for you, right? How is it, being a father of two?" she asked. He looked at her, suprised that she considered him as a father of two. He knew she accepted him but still he got that feeling she was still rooting for Emmas biological father, although she knew the whole story. "Well, it's exhausting, stressful, sometimes soul-destroying, but hey, loving every minute of it."
Emily smiled slightly. "I've read your last book."
"Huh."
"I liked it. Richard always had a thing for books, you know. I wanna keep up with that."
Jess smirked. "Don't know if I had the approval of Mr. Gilmore, but nevertheless, thanks for the kudos."
"I think he would soften up knowing your son is named after him." They both shared a glance.
"But no sentimentality", she continued, "how's Hartford doing?"
"Good. It was a bit of a compromise. Commuting between Queens and Stars Hollow to see Lorelai and Luke was like wasting time and gas. And Hartford offered better schools for Emma. So yeah, it's okay. In fact, I've never been a Queens guy. Not even to begin with Stars Hollow. A weekend? Fine. More days? Soul Asylum. Not the band. "

The door squeaked behind them and Rory appeared, dressed in one of her ugly Christmas pajamas. Jess glanced at her and thought she never looked more beautiful. Their eyes met.
"Hey, there you are. Oh, and grandma. Hi. Am I interrupting something?" she asked, still a bit confused.
"No honey, just a chat. Come, sit with us." Emily responded. Rory sat down, next to Jess, sitting cross-legged to warm up her feet. He put his arm around her. "Rick's sleeping?" She nodded.
Emily watched them. "You know, just the three of us sitting together is quite some time ago. In fact, 20 years? Or more?"
Jess rolled his eyes. "Please, don't. That wasn't a decisive moment in history." Rory laughed. "Oh, I didn't thought about this for years. Grandma, I really have to admit, you've played it cool."
"I didn't have any other options. I was afraid that I'm next one with a black eye", Emily countered.
"Please." Jess groaned. He went through his hair with his fingers.
"But Grandma, I never cleared it up. It wasn't a fight or something like this. It was a football. So, no hoodlum activity" Rory clarified. Jess cleared his throat and gave them a fake smile.
Emily laughed. "Enough of that! We look forward to even better times. No black eyes. At least not yet. Ricky hasn't started walking. So, let's call this a day, I'm going to bed. Good Night, you two." She smiled at them and patted Rory on her shoulder before she left the room.

"So, just the two of us. Candles. Romantic." She beamed at him. "Yup. Grandma's living room. Is that your kink?" he answered with his crooked smile. She slapped him. "Oh Jess, you're awful."
He leaned over and bit her earlobe. "In fact I already know some of your kinky secrets... and you know what my biggest kink was when I was a black eyed teenager?" "Hmm?", she asked, not opening her eyes, feeling him trailing kisses down her neck. "Blue-eyed, innocent girls who got liquid as wax under my hands... eliciting their sweet moans on shabby couches and storage rooms." She blushed. "Oh how well do I remember. In fact especially when you got that black eye. It was a bit of a turn on for me." He smirked. "Oh yeah?"
Rory sat up and straightened her shirt. "In fact, I remember that I've talked to Mum around this time that I'm considering having sex with you."
"Rory Gilmore's biggest kink are bad boys. I like that."
She threw a pillow at him and sighed. "I'm sorry that everything turned out different."
"We've talked about it, Ror. No hard feelings." Jess kissed her. "I mean I would have totally ruined you for anyone else coming after me, so, no biggie, be happy." A grin was plastered on his face. Rory shook her head. "I love you for being so humble. C'mon, let's go to bed and ruin the night." She got up and took his hand. He sighed. "Yeah, if you mean let's go and ruin the night by a wailing baby, then we totally get lucky."