2016

"So Gilmore, will I ever be honored to read your chapters?" an amused voice came from behind.
Rory smiled and noticed him sitting next to her. "You're just curious if you're more the James Dean type or the Stars Hollow Pennywise clown" she teased. He laughed. Still, she liked to make him laugh. Although he's more mature, more willing to communicate, she remembers the time when she was almost the only one who could make him crack up, who opened his personality, his witty humor. He lifted his glass. "Cheers" he stated and winked. "I'm happy for them. Finally. And I saw it from the beginning." "You?" she grinned. "Since when are you Hitch the Date Doctor?" He rolled his eyes. "First evening at your house, 15 years ago. I've asked her if she's shagging my uncle."
Rory gasped, but only to burst into laughter. "You didn't!" He just smiled.
She swallowed. She wanted to ask him something, actually already yesterday when she told him about the three chapters. But when she rushed after him, there was also Luke and she suddenly was afraid. So she just squealed like a little girl, grabbed Jess by his jacket and left again. Truth is, she felt intimidated by his presence. He became such a good guy, successful, content with his life, doing what he likes to do. She wanted the same for herself.

After the "Philadelphia incident" they've met two or three times, when his sister Doula was born (awkward, too early, pretending that nothing had happened), to Luke's 45th birthday (she's sure he just showed up to annoy Luke, it's their way to show affection) and oh yeah, some four years ago. She was in Philly for some days for a business meeting and knew from her mum and Luke that he's doing some authoring at a local book store with his sequel (obviously she's not the only kid to be super-proud of) and she couldn't help it, she went. Hearing his voice, reading out of his own writings, seeing him there, this made her happy. When he saw her afterwards, he smiled mildly at her. They chatted for a while, nothing serious. Some girl approached them, his eyes lightened up and she asked "Shall we, hun?" with a playfully smile, just to disappear in the crowd, making her way to the door. Jess said goodbye to Rory, left her standing in this small store, full with people, but she felt alone.
She knew it's not fair. They've always had a certain connection, straight from the start. Although they didn't date as long as she dated Dean or Logan, it was different. There was never a real closure and she knew that for Jess a long time it wasn't over. Call her selfish, but she liked it. And now, seeing him moving on, leading his life, made her happy and jealous at the same time.
Four years later and there she was. Broke, unemployed, single, pregnant. And he's sitting there, radiating his independent vibe, looking good and these upper arms, damn, he's buff. She blushed. No wonder why she felt like seventeen again, when he visited her some weeks ago at the Gazette, made her jabbering about missing underwear and surrogates, only to be left speechless after his advice to write a book. To feel passion for something again.

"Jess?" she asked quietly. He looked up, he always had this intense gaze. "I know you're a successful author, you have other work to do... and you're definitely not in my debt...", she continued, "but as long as you're like my life's voice in taking me back on track when I feel shitty and empty, there is something I have to ask you. I'm not offended if you say no, don't worry, but..." "Geez, shoot." She breathed in. "Would you like to be my editor?" She squeezed her eyes, afraid of hearing the answer. "Sure." She opened her eyes. "Sure?! That's it? That was easy." He laughed and took another sip. "No biggie. I'm happy to help. Maybe this way I can twist the story of me being Pennywise. Oh, and add to it, I feel a bit dizzy. This booze is way too good."
Rory chuckled. "Thank you, Jess. Really. For everything." He took the bottle from the table. "Let's talk about it when the surrounding is not that blurry. Helps with the reading as well. You want some?" he asked. "No thanks, I've already made my experiences with Miss Patty's leftover punch. I'm fine with that cranberry stuff. It's so European." "Classy. You know 'Never Have I Ever'?" He took two glasses and filled them with booze and juice.
"Never have I ever aced a test without studying?" He smirked. They both took a sip.
"Never have I ever ended up in prison?" His eyes widened as he saw her raising her glass. "You have to fill me in." "I've stolen a yacht" she admitted. He grinned. "Lorelai must be so proud of you."
She sighed. "Next one. Never have I ever gotten a tattoo?" Jess didn't look her in the eyes while swallowing the liquid. She laughed. "Oh boy, now YOU have to fill me in." He shook his head. "You have no idea."
She suddenly felt more confident. "Never have I ever had a one-night-stand." Their eyes met. Simultaneously they grabbed their glasses. He licked his lips. "Rory Gilmore, you surprise me." "It was a Wookiee." "What?"
"Never have I ever broken someone's heart" she continued. He looked up. "Rory..."
"Well, I think we're both good at this" she whispered. Her eyes filled with tears. "Oh, a last one. A good one. Never have I ever got knocked up by an engaged man..." she stuttered.

And there it was. Silence. She didn't dare to look up. Instantly she felt nauseous. Why did she say this?
Jess coughed nervously and broke the silence. "That explains the not drinking part although you seemed to enjoy having scotch for lunch some weeks ago." He loosened his tie. "So, the baby's going to be hairy? Middle name Chewbacca?"
She lifted up her head in shock. "What?" He cleared his throat. "Sorry, I guess it's too early to make jokes. Look, I'm good with giving advice when it comes to your abilities, because you know, I believe in you. Always have, always will. But I'm not the best source of parenting stuff."
She sighed and wiped her eyes. "I know, look, I know, Jess. I'm sorry to bother you with that. I just don't know on which crossroad I took the wrong direction. I'm 32 years old. I'm an adult. But I feel lost. And talking to you is the only thing that makes me feel real again. Although it's not fair, you're my ex-boyfriend, there was always the wrong timing, you deserve so many good things and not my selfish whining about my personal failures."
Jess shook his head. "Your baby is no failure, okay? And everything else can be fixed."
She bite her lip. He was right, the baby was no failure. Her decisions maybe, but not this little creature.
"Thank you." Her voice was quiet. "It's just... scary. I know that the baby's father won't be involved that much. Maybe financially, but..." "Hey", he stopped her, "it's okay. Look at us. Our fathers were also not singing us lullabies and reading us bedtime stories. And I think we turned out pretty well. Family isn't always blood. It's the people who really want you in their lives."
She smiled. "Who are you? And from where did you get all your wisdom?
"I may not be a Wookiee, but call me Yoda. Hey, never have I ever danced with a Lorelai Gilmore. Although I'd have two options." He stood up and offered his hand. Rory felt giddy and took it.

His scent, his strong torso, his healing words. All together gave her hope and a familiar feeling. Her head was resting smoothly at his shoulder, the awkward feeling was blown away after some songs. "Never have I ever met someone that understands me as well as you do", she whispered in his ear. As an answer, he smiled silently and drew closer to her.