This came to be after several rewatchings of the revival and the realization that I don't very much like who Rory is in the revival. It also came from watching Colette Butler's YouTube video titled "Letting a Dream Die" - while it's not imperative you watch it to understand this video, it is wonderful and played into this fic greatly. I'm planning on this being about five chapters, at most ten.

Disclaimer: Are these still necessary? Probably. I don't own anything, I merely worship at the feet of the Palladinos.

She was wired in spite of not having had a single sip of coffee and having been up the entire night being a witness to her mother finally marrying the man of her dreams. She sat with her knees drawn up to her chest and breathing deeply through her nose in effort to keep down the bowl of fruit her stepfather had brought her upon the news that he was going to be a grandfather – her kid was definitely a Gilmore because the fruit was slowly coming back up her throat and all she wanted was a big stack of chocolate pancakes. Her mother and Luke had gone home to grab a few hours of sleep (at least that was what Rory was choosing to believe) before their actual wedding ceremony. Lorelai had kissed her daughter's forehead before she left, smoothed her hair back from her forehead and cupped her chin in hand, with a promise that she wouldn't let Luke throw out the coffee or slip her decaf. She had smiled and stood to throw her arms around her mother; feeling so much like a little girl again while simultaneously feeling every bit of her thirty-three years and then some. Luke had given her a quick hug and made her swear to grab a quick nap before the ceremony. She had watched them walk down the street completely wrapped up in each other until they disappeared around the corner toward home.

If she was being honest, Rory Gilmore was not very fond of herself these days and she hadn't been for quite awhile. She had landed so far away from the dreams and aspirations and ideals she'd built up for herself and in some ill attempt at coming to terms with that she had become someone she absolutely couldn't stand. Someone that the Rory of years prior would have hated.

And now there was a life depending on her, needing her to get her act together.

Tears slipped from blue eyes and she tried to wipe away the evidence of before anyone could notice. Suddenly, she understood what Naomi Shropshire meant by standing a metaphorical ledge. Rory was on a ledge, her feet barely still on solid ground. Exhaling slowly, it was time to take a step backward. She unlocked her cellphone and dialed a number that should have been far more familiar than it was before raising the device to her ear.

"Hello," he answered.

"Paul," she greeted him with a cracking voice. "I, uh... I got your text. And you're right. We should breakup... I'm not contesting that. I just, I want... I need to apologize to you. I treated you like crap for nearly three years that I was barely present for. You deserved so much more than what I was giving you. You were kind and sweet and generous while I forgot about you, lied to you, and evaded you. And I'm just... I am so sorry."

"Thank you." Paul's voice was soft and full of disbelief. "I... Are you going to be okay?"

"I'm working on it," Rory promised. "Please go find someone to be happy with."

"You too," he requested. "You should get to be happy too."

"Thanks." She scrunched her face in an effort to hold the tears at bay. "Bye."

"Goodbye Rory."

Unable to hide the tears any longer, she let them fall and prayed that the nosiest of Stars Hollow citizens were still sleeping as she unfurled her legs and walked with her head down to the diner. Given the early hour, it was thankfully mostly empty except for Jess behind the counter, Caesar at the grill, and a few elderly old men discussing the good old days over cups of coffee.

Jess caught her eye and frowned. "Why are you crying? You've scored the best stepdad ever. Comparatively. I mean, I have to spend holidays with TJ."

She released something between a laugh and a sniffle as she smiled at him. "I'm telling Luke you said that."

He poured a mug of coffee and slid it over to her. "If it'll make the waterworks cease and desist then go for it."

"Whatever, you softie." She took a sip and then frowned and spit the liquid back into the mug before pushing it away with a whine as she dropped her head to the counter. "Dammit."

Jess was quiet for a long moment as he removed the mug of coffee and replaced it with a glass of water. She refused to lift her head to look him in the eyes and he was stubborn enough to wait her out. He leaned in close to her and softly breathed against her ear. "So how far along are you?"

Her head shot up from the formica counter with a gaze caught somewhere between a glare and a bewilderment. "How?"

"Rory Gilmore can't stand the taste of coffee after being up all night? C'mon. Give me a little credit here. Plus not being able to stand the taste of coffee is like the biggest cliché ever."

She sighed. "Six weeks. Doctor confirmed it yesterday."

"Congratulations?" he offered hesitantly. "Or do you need a ride to the clinic in New York?"

"Congratulations is fine," she told him.

Jess quirked an eyebrow. "Then why do you look like you're ready to start crying again?"

"Can we talk upstairs? This town has too many busybodies."

He nodded and led the way behind the curtain up to the old apartment his uncle only kept as such for when Jess came through town or April wanted to exert her independence over her summer breaks. He tried not to think about the last time he had been alone with Rory in that apartment as he sat down at the table because the couch felt like a ticking bomb of memories.

"The baby is Logan's," she explained as she took the seat across from him. "Logan Huntzberger. I think you know him as 'The Blond Dick at Yale'?"

He huffed a laugh. "Actually I now know him as 'The Blond Dick Heading the Biggest Publishing House In All of Europe' but that's a little wordy. I guess I'll also have to add 'the guy who impregnated my ex-girlfriend-slash-step-cousin'."

"Ugh." She scrunched her nose and waved her hand. "I... Luke is my real dad as far as I'm concerned but, uh, I cannot be related, even by marriage, to someone I made-out with."

He laughed. "Fair enough. So you spawned with Logan and this is bad?"

"He, uh... He's engaged to some French heiress who fits perfectly into the Huntzberger plan," she explained. "And up until about an hour ago, I was dating someone that I treated like crap."

"The infamous 'P'?"

"Yeah." She worried at the her thumbnail. "I've become someone I hate. Someone who doesn't learn from her past mistakes and is terrible to people who care about her. Who can't let go of a past love. God, I've become my father."

"Never had the pleasure of meeting him but I'm assuming he's your mother's 'Blond Dick at Yale'? Just from what I've heard over the years."

"Yeah... That's fairly accurate." She crossed her arms over her chest. "I had all these dreams, you know? I've been dreaming of being a journalist for years; since Luke was watching me for an afternoon and the only thing he had for me to read was a copy of the Gazette. I was going to go to Harvard and I was going to be the next Christiane Amanpour. I was going to find the love of my life who kept me supplied with coffee and understood that I would spend months in the Middle East reporting from foxholes."

"Well, ya know, that war is supposedly over so I doubt you would have been doing much foxhole reporting."

She rolled her eyes. "I have a thirty thousand dollars a year degree in Journalism from Yale University that I'm wasting trying to save a dying small town newspaper. I've been the other woman twice now because the first time wasn't stupid enough for me apparently. I stole a yacht. I dropped out of Yale. I mean, I went back but still... I... I don't think I've liked myself for a long time now, Jess."

"You're gonna be okay," he promised and reached into his pocket to pull out his wallet. He removed a business card and slid it across the table to her. "Luke doesn't even know that I went to therapy once I moved back East... because I had become someone I didn't like very much."

"Jess..."

"If you don't want to see the same guy as me," he explained. "There are plenty of other great guys in that office. I've been going to him since I moved back to Connecticut to run the Truncheon annex. It helps, Rory."

"You've gone to therapy?"

He nodded. "You're going through a lot. Your childhood dreams need to change and you gotta become someone you like again. You're growing a life that needs you to. I think... I think you've been through more than you realize; your dad flitting in and out of your life, me being a kind of toxic boyfriend, all the shit you've gone through with Dean and Logan. It's a lot. And now you're adding pregnancy hormones to the list. It might be good to have a place you can go that's like a pressure release valve."

"Thank you." She picked up the card and rubbed it between her fingers. "For everything. You're not the angry kid you were when you broke my heart... I see that now."

"Yeah?"

"Yeah." She cleared her throat. "You have this way of seeing me without the rose colored glasses and you aren't afraid to give me a good hard yank to pull me back on course."

"You're never so far off course that you can't find your way back," he told her as he placed a hand over hers. "You'll get through this, Rory, and you aren't alone."

"I know. I have mom even though she nearly stroked out when I told her and Luke's already planning to baby proof the Crap Shack."

He smirked at that and then looked her in the eyes. "And you've got me. I know I wasn't someone you could depend on at seventeen but I'm older and steadier now. I'll be the best ex-boyfriend or step-cousin or insert-appropriate-title-here."

She gave him a small grin and felt herself start to relax, the world starting to come back into focus. "How about friend?"

"I can work with friend," he promised. "You need sleep before you fall over walking your mom down the aisle later."

"You're the best man," she told him. "You'll catch me. Right?"

"Of course I would," he promised. "But instead of creating more fodder for this nutty town you should go crash on the bed for a few hours. I'll go finish helping Caesar and wake you when it's time to go meet Lorelai at the inn for all the girly stuff."

"I could just go home."

Jess hook his head. "Nope. I am not sending you home in your delicate state to whatever the newlyweds are doing."

"God!" She wrinkled her nose. "I'm hoping they're asleep. They were up all night."

"Oh I'm sure they're at least in bed."

She laughed. "I'm gonna strangle you."

"No you're not." He stood and helped her from the chair then led her over to the bed that was April's. He pushed her gently down to the mattress and pulled the blanket from the foot up to her chin. "Go to sleep. You're growing a person and that's exhausting."

She gave him a sleepy smile. "Hey," she called after his retreating form. "You're a good friend."

He smiled back. "You're gonna be a great mom, Rory."

When the door was clicked shut behind him, she rolled onto her side and curled her arm under the pillow as her free hand settled low on her abdomen. "We're going to be okay, little one. He's technically a Mariano but we got a Danes looking after us and I know firsthand that they're the best there ever was. I love you. We'll be okay."

And then her eyes fluttered shut as she gave into the siren call of sleep.