"And how far along is it?" Rory Gilmore looks at the tiny screen in the doctor's office. She at an apple a week ago and when the test came up positive, she found herself making an emergency appointment

"False positives happen all the time." She thought to herself as she dialed the number in a panic. "How could this happen? I'm careful, I'm always careful. Plus, he's getting married. I can't be. It would ruin everything." It was the first time they weren't fully protected. It had been a few weeks since she called it off over the phone and with no hopes of intimacy any time soon, Rory had been a little less than zealous about her pills. But she had only missed a few days, and it was in the heat of the moment. Shouldn't she get a pass for that?

The Hartford gynecologist looked over from the sonogram screen. "You're about eight weeks pregnant." She looks down at her clipboard. "All looks well with the baby, I'm sure your husband will be thrilled."

"Yeah. Thrilled." It wasn't possible.

Rory Gilmore, 32 years old, unemployed, living at home. Pregnant.

On the bench outside the doctor's office Rory was flipping through her calendar, trying to figure out a way to explain her situation to her mother. "I could buy an apartment in Stars Hollow and tell her that I've been trying to have a baby through Paris's clinic." She wasn't sure that Lorelai would buy the sperm donor story at 8 weeks along. She flipped through the calendar on her phone trying to figure out when she would've been able to get away 8 weeks ago and be inseminated.

Something wasn't adding up.

8 weeks ago was a month before Logan surprised her in Stars Hollow.

Previously

Rory Gilmore was in the middle of prepping the layout for the fall edition of the Stars Hollow Gazette. She wanted to have the final lay out ready by the morning and it was already 11 at night. Her two geriatric employees retired at 6 so it was just Rory alone in the office.

The coffee pot broke earlier that week when Esther knocked it over trying to find her glasses. She was dying but determined.

Picking up her phone in distress she dialed the diner, knowing that it was probably closed. A familiar voice picked up. "I'm at the paper, I need coffee." She could here the voice breathe heavily in exasperation on the other end of the line.

"I'm trying to sleep here."

"Please."

The voice reluctantly agreed.

A few minutes later there was a rapping at the door, and a figure armed with two cups of coffee and a bag of donuts barged into the office.

"Why don't you just go home and pick up in the morning? Its not like Taylor is going to care whether the paper is 2 or 10 pages long, as long as you don't skip the poem." Jess plopped himself onto the chair across from Rory's desk and flung the donuts and coffee down. "That would be the end of the world."

"I know, but this is my chance to really revamp this paper. You know, do something different."

"You work really hard to not get paid."

Rory was exhausted. She gulped down the coffee and grabbed a donut. "I think I might need more."

"Did you actually think one of these cups was for me?"

She smiled and went back to her task. Jess stared at her for a long moment. "So how much more do you have to do?"

"Only the last page." She said bending over the large table where all the article clippings were laid out. She was having trouble getting Doyle's review of Suicide Squad (he called it a triumph and that it "got everything right that Nolan got wrong") and Miss Patty's gossip column to fit in with Al's half page ad for 50% off all Indonesian desserts.

Jess got up and walked around to the front of Rory's desk. He grabbed the bottle of scotch from the bottom right drawer. "I think its about time for a celebration then." He poured two glasses.

Rory slurped down the rest of her coffee, cutting out Doyle's review. 'I'll just throw it up on the website for him.'

"Come look at it, I think I'm done." Jess walked over and nodded, handing her a glass. "Scotch and donuts, my favorite combination."

"You're gonna die at 40." Jess walked back over to his chair. "Have you given any more thought to that novel?"

Rory pulled up a chair next to him. "I've outlined to the first five chapters."

"You move fast Gilmore." He gulped down the rest of his drink and poured another.

"Will you read it?"

"The outline?"

"Yeah, to make sure my continuity works and stuff."

"Depends. Am I in it?"

"Yes. I was going to ask you first but you did give me the idea."

"How could I pass up a chance to read about myself then?"

Rory got up to retrieve the outline while Jess poured her another drink. She brought it back over and dropped the outline in his lap. "Now I did change the names, and its not perfect but its where I have to start." Nervously, she slurped down her fresh scotch and poured another.

Two more scotches each and 10 minutes later Jess finished scoping through the outline. "Did your grandparents really try to force marriage on your mom?"

"It was how it was done in the old days."

"Geez." Jess poured another drink, took a shot, and poured some more.

"What did you think?"

"You have a really nice foundation here Gilmore."

Rory was feeling a little tipsy. "You know you were probably the best."

"The best what? Ghosting expert?"

"No matter what happened, how shitty you were, how stupid and naïve I was, you always encouraged me. If it wasn't for you I would've never gone back to school, I would've married Logan when he asked, and now I would be one of those DAR housewives."

"I am pretty wonderful. But seriously, you didn't need me. You would've figured it out."

"You got me there faster. I still wonder what would've happened if I had picked you that night when your book was released. Or if I ran away with you when you asked me to."

"We would've had a whirlwind romance and broken up as quickly as we got together."

"No…"

"We were young, I was stupid. And we didn't want the same thing." Jess poured another glass.

"Why didn't you have another serious relationship?"

"Like I said, nothing stuck."

Rory leaned her head back put her feet on the desk. "Do you think you'd ever want to get married?"

"You know, there's only ever been one person that has even made consider settling down. But she isn't ready to settle."

"Must be a hell of a woman."

Jess looked at Rory for a long moment with her head back and her eyes closed. She was still that 16-year-old he saw sitting at the diner with her mother a life time ago. "She really is."

"You think she'll come back?"

"I'm not one for sentimentality – "

"I'm shocked." She tilted her head up to look at him, those blue eyes piercing his soul in the dimly lit newsroom.

"Yeah yeah… I'm not one for sentimentality – and you know that – but," He stared intently at her, "I would be willing to wait for this girl forever."

Rory Gilmore was drunk on sugar and whiskey. And blame it on the alcohol, but in that moment she found herself, wrapped up in a life time of what ifs, leaning into her ex boyfriend. The moment their lips touched, she was 17 and they were in the alley behind Gypsy's. It felt right. It felt like youth, it felt like she could start her whole life over. A life where she never thought to drop out of Yale, where her grandfather was still alive, where Logan Huntzberger wasn't engaged to someone else. A life where maybe Jess never left to find himself, maybe she did run away with him, and they were on the road living the life foretold in beat poetry together. She would've never fallen in love with Logan and her heart would never be broken.

They fell together like no time had passed, it was a religious concoction of scotch and unrequited attraction finally exploding. It was the full devotion Rory had never felt with Logan or Paul and that Jess had never felt with the one-night college girls that had become his taste.

They didn't even seem to care when the condom broke. Well Jess didn't. Rory just didn't realize.

They lied there in the heat of their passion, Jess completely content. Maybe this was the start, his chance to redeem himself with Rory.

Rory sat up and started to put her clothes on. "If only Logan was like you." She put on her shoes. "I'm sorry for waking you up."

"…. Its no problem." He muttered as she began to clean up, he quickly got dressed and left without a word.

Rory shrugged.

The Gilmore House, day before the wedding

"You're completely over it?" Luke asked Jess.

"Oh yeah, for a long time." He wasn't over it.

It had about two months since that night with Rory and Jess still had dreams of it every night. But at the end of every dream Logan would show up and whisk Rory away as she laughed at him. She had brushed it off so casually, a drunken tryst.

They had talked about it, she apologized, he agreed it was wrong.

Luke walked back inside as Jess picked up his duffel bag. He knew that she was never going to love him again, because when she did he ruined it over and over again. She started to leave the house but his desire caught him off guard. "One last look." He thought too himself. He walked over to the window, there she was, giggling with Kirk and Lorelai. She would never love him again and he knew he now needed to accept that.

Now

It was a mistake. A stupid drunken mistake.

That's what Rory thought as she drove. She didn't even really know where she was driving.

"It's not like he even cares about me. I haven't seen him in four years, whatever we had has been over for a long time. Plu,s I can't ruin his life with this, its complicated enough without adding the 'hey so I have a kid with my high school ex girlfriend that I had a one night stand with 15 years after we broke up' to his resume."

The night of the act was still fuzzy to her. She remembered the main points, but most of the detail and all of the conversation was gone. "If only I could remember what happened." The morning after she had woken up in the newsroom on two chairs, Jess was gone. They both agreed it was a mistake.

While Rory was convincing herself that she could do this on her own, she found herself at her dad's office. She cried in her car for an hour before going in.

After the wedding

It was beautiful.

Lorelai and Rory sat drinking champagne on the steps of the gazebo. Well Lorelai drank, Rory poured it into the grass every time Lorelai looked away. Her mother was so happy, she was glowing.

Rory couldn't concentrate. As her mom talked she realized she couldn't take the secrecy any longer. She and her mom didn't keep secrets. Rory didn't know what she was going to tell her but she knew she had to say something.

"Mom."

"Yeah?"

"I'm pregnant." Lorelai looked over at her shocked. She sat there for what felt like forever, couldn't finding the words to say.

"You're pregnant?"

"Yeah."

"How?"

"The normal way, birds and bees. When a mommy and a daddy love each other very much – "

"I know how it happens, obviously. But what I mean is… oh my god… Rory," she began to look somehow terrified and disappointed at once, "Rory, is it Logan's?"

Rory looked at her shoes. Tears began to well in her eyes, she could barely talk so she whispered. "No."

Lorelai, now confused, stared into space. "Then who's it? Please don't tell me is Percy's."

Rory began to laugh through the tears "Its Paul, and no, its not his."

"Then what? Did you have a 3 night stand with the wookie? Are you in Paris's army of surrogates and its actually the baby of some guy from West Virginia and is 65 year old wife?"

"You wouldn't believe me if I told you."

"I had a baby at sixteen who grew up and went to Yale. I am a lifetime movie. You could tell me you're having a baby with Taylor and I would believe you."

"Its Jess."

"Nooooo…" she moaned incredulously.

"Could you please not tell anybody?"

"Rory… this is… I don't even know what this is."

Rory bit her lip and wiped away her tears. "I have to go." She got up to leave.

"And where are you going to go?"

"I have to… I have to do something really quick." Rory ran down the street. She ran until she couldn't anymore. When she finally stopped she found herself in front of the most terrifying house on the block.

Rory ran up the sunflower yellow steps and banged on the orange door. She banged for what felt like hours when TJ answered. "Rory, chill out. You're gonna wake up Doula."

"TJ, is Jess here?"

"Well yeah but he's been up all night with these bad dreams. So I wouldn't wake him if I were you." TJ's accent made even grammatically correct sentences sound unintelligible.

Rory walked inside and straightened her dress and hair before heading to the living room where Jess would be sleeping. She barely knew what she was doing, as she moved into the living room she felt drunk. She felt as if she was moving but not by choice, like autopilot.

She looked at him while he slept for a few moments. His hair was shaggy and he hadn't shaved in days. He looked old, older than when she met him at least, but still had that mystery. Finally she nudged him. Groggily, he opened one eye. "Rory?"

"We need to talk."

"Why?" He sat up, his tshirt twisted around his frame, hair hanging like curtains around his face.

"What happened? You know, that night. At the gazette."

"You know what happened. I brought you coffee, things escalated, you told me you wished Logan was like me, I left. It was a mistake." The word mistake hurt her.

"I talked about Logan?"

"It seemed like you wouldn't stop talking about him."

"Did anything else happen? Anything with protection. Like was it used?"

"What is this, shawshank?"

"Jess."

"The condom broke, but you knew that. I asked if you wanted to stop, and you giggled and through it across the room."

"Shit."

"Language! My little sister will be up any minute."

"Jess."

"Yes Bob Woodward?"

Rory tried to make the words come out, she just looked at him in all his early morning grumpiness, and started crying. She sat on the coffee table and sobbed in her hands. Completely awake by the sight of a crying girl in his parent's living room, Jess moved to comfort her. Rory just pushed him away. "Rory. What's going on? You can't just barge in here at – what – seven in the morning, wake me up, and start crying."

Rory couldn't speak, she just sobbed.

"You want some coffee? I'm gonna make some coffee."

"No." Rory squeaked. "I can't."

Jess was standing in the doorway to the kitchen now "What do you mean you can't? You can always do –" Jess looked over at Rory who was holding her stomach and sobbing.

Rory realized he had stopped talking and looked up at his stunned face. "Jess."

"Oh my god." He didn't know what to say, he turned and walked into the kitchen.

"Jess! Please!" Rory ran toward him. He turned to her.

"Logan must be a very happy man." He turned back and began to move away from her.

"Jess –"

"Why did you tell me this? Was it to rub it in my face? Look at me, I'm Rory, I had sex with you out of pity and now I'm having another man's baby but I'm going to build suspense when I tell you because he's getting married and the condom broke."

"Jess – "

"No, you know what Rory, I can't do this anymore. I waited for you for 15 years. As much as I tried to move on I couldn't because every girl I dated was nothing compared to the Great Rory Gilmore. And now this. Thank you because this made it a lot easier."

Rory stood there, unable to look up, shaking and defeated "I'm moving to Queens…"

"Good. Just stay out of Boston." Rory ran out of the house.

A few weeks later

With Christopher's words about the unstoppable force that was Lorelai and Rory's relationship, as well Jess's words, she began to pack up. She had found a steady job writing for a tabloid and an apartment in Queens that Christopher agreed to help her with until she fully got on her feet. Rory felt a renewed sense of purpose because it was no longer just her future at stake.

She hadn't bothered talking to Logan and had barely left the house in avoidance of Jess, Luke graciously offering to go to the diner when they wanted to meet.

Her mother's happiness didn't make her plight any easier but Rory tried to stay out of the newlywed's way to avoid bringing them down. She wasn't even sure if she could bring her mother down. In addition to the new marriage, Lorelai had thrown herself into going through boxes of Rory's old baby clothes and taking trips to buy new ones. One thing Rory wouldn't be short on was baby clothes whether it was a boy or girl, between what Lorelai had and what Sookie and Lane brought over.

"Are you sure you don't want to just stay here? Just for the first year so you have help." They would ask.

"I have to do this away from Stars Hollow." She would answer.

Rory Gilmore, Yale Graduate, Award Winning Journalist, Single Mother. She almost felt like she could pull it off.

Rory had all her boxes packed and was heading to Queen in the morning. She had a nice dinner with her mom and Luke and her Grandmother was coming up in the morning to help her move in. Emily was still alarmed that she was becoming a great grandmother.

After dinner, Luke excused himself so he could go check on the diner. Cesar was supposed to leave early that night. Only an hour after letting Cesar off, he closed up. But before he could lock the door his nephew, who was supposed to be in Boston, barged in. "Jess."

"Hi."

"Why are you here?" Luke vocalized, visibly angry.

"I have business in town. Can I crash upstairs?"

"She's leaving in the morning."

"Who?"

"You know who."

"Hmph… good riddance."

"You shouldn't be talking about her like that. What's gotten in to you?"

"What's gotten in to me? That girl strung me along and then metaphorically punched me in the gut when she told me she was pregnant. She was rubbing it in my face."

"How could she rub it in your face? She had no job, no place to live, and on top of that she's having a baby and you just pushed her away. She's struggling and yet she's still moving to New York because she keeps a sliver of hope that maybe things can be like they were a year ago."

"So Logan went back to his beautiful bride then?"

"What are you talking about. Logan has nothing to do with this."

"He's the father so I'm pretty sure he has a lot to do with it."

Luke's face softened to concern "You don't know."

Jess was still raring to go "Know what? I know all I need to."

"Jess – Logan isn't the father of Rory's baby." This took Jess by surprise.

He began to stiffen, realizing exactly what he was about to find out, what he was too stupid to see weeks ago when Rory tried to tell him.

He looked up at looked, he couldn't decide whether to be terrified or excited. "Then who is?"

"You are." Before he could finish his words, Jess was out the door. He had ruined his last shot with Rory, but maybe, just maybe, he could have a second chance with his child.