If you haven't read How Did I Get Here, you might want to. I did write it second, but it's a prequel to this story.

Disclaimer- Gilmore Girls and the characters associated with the show are not mine.

Chapter One: Pro-Con lists never lie.

Telling herself the pro-con lists never lie, she paid the driver and climbed out of the cab. Glancing once at the Truncheon sign above her, she fixed her eyes on the door and pushed it open. Anyone who knew her would have recognized her stubborn face. Pausing in the entry, she searched the aisles until she saw him.

"Jess? We have to fix it! She's doing it again, pulling away, closing down. If he doesn't ask her to marry him, she's going to take the job!" Rory ranted as she stalked his direction.

"Rory? What are you doing here?" Jess asked, his heart racing at the sight of her. He shouldn't be surprised. He'd finally quit looking for her, so of course she was here.

"I told you, I need your help. You have to talk to Luke," Rory crossed her arms in front of her chest, every nerve ending aware of his scent as she breathed in the sight and smell of him. "They're stuck; it's been four years since their reconciliation. I know they wanted to start slow, but this is ridiculous. She's not going to ask Luke this time, and she's beginning to believe it'll never happen. I hear the defeat in her voice every time she mentions his name, and when I visited she told me the Durahm Group had offered her another job. She's considering it, Jess. She's going to leave Stars Hollow," Rory had tears in her eyes as Jess took her by the arm and moved her up the steps to the Truncheon offices.

"Here, sit down," he said as he poured her a cup of coffee and set it on the desk. "I know he planned on asking her, we talked about it, but it was ages ago. Did something happen?"

"Not to my knowledge, she's never mentioned any fights. She's afraid he can't commit. That he hasn't forgiven her for Christopher." Rory replied in between sips of coffee, grateful for something to do with her hands. Seeing him was as intense as she imagined, she had already ranted, rambled, almost cried, and now she'd probably have to beg.

"Why do you think I can do anything?" Jess asked, trying to maintain his equilibrium while his world was being dismantled by her presence.

"Because you're the one who always talks sense, makes us see the truth, and I can't. I have to get on another bus. I said I'd never ride a bus again after the last time, and I signed up to re-do the whole thing!"

"I thought you were working for the Times? Why do you need to get back on a bus?" Rory looked at him over her cup, silent as she digested the idea of him keeping tabs on her. After the last time she was here, she figured he would've avoided any mention of her life. Something to ponder later, but not here. Not now.

"After Obama won, I managed to get the job at the Times, and have been there ever since, but I started to feel like I was in a rut. When my old boss asked if I wanted to do a 'four years later' retrospective, I jumped at the chance."

"You left a job at the New York Times to go back on a campaign bus for an on-line paper? I'm sorry, I can't wrap my head around the idea…" Jess replied.

"I know, I love reporting, but I liked being the editor at Yale better. I guess I needed more of a challenge, something different anyway, but what are we going to do about mom and Luke?" Rory replied, ignoring his familiar smirk despite the swarm of butterflies in her stomach. Jess was quiet for a moment before running his fingers through his hair and sighing. Rory knew she'd accomplished her mission.

"I have an idea. We're both writers. Here," he said, as he handed her a piece of paper and a pen. "Write to your mom. Make her hold off on taking the job. I'll add to it, and tell her I'm going to talk to Luke, because I know he wants to marry her."

"Okay. Let me think for a minute," Rory said as she nibbled on the pen cap. Jess watched her, the expressions crossing her face, the play of light across her hair as she bent toward the paper. Running his hand down his pocket, feeling for the pack that was no longer there, he turned away. It had been years, and what he felt wasn't buried deep enough. "Dig a hole, throw it in, bury it, and bury the shovel" Luke had said once. He tried. He had, but his heart was clawing its way up through the dirt again.

"Here, see what you think," she said, moving away from his desk. Turning at the sound of her voice, he sat down to read.

Mom, remember when Grandma said she tried on her wedding dress every night before marrying Grandpa? And you had us jumping in the car days before you were supposed to marry Max because you didn't want to try on your dress? I know you tried on your first Luke dress all the time. I'm going somewhere with this, I promise.

You never asked me why I said no to Logan. I know I told everyone that I wasn't ready, I had dreams and plans. There was more to it. There are great papers out West too, and with the right person, I would have sacrificed my dream of the New York Times. I'm surprised you didn't catch my lie. No, the truth was, when I closed my eyes and pictured walking down the aisle, I didn't see Logan. I know when you close your eyes and picture yourself walking toward someone you see Luke standing there, waiting for you. You probably even see your dress, and I bet your imagination drapes you in it every time.

I know Luke is ready. For whatever reason he waited (probably for some insane perfect moment) and now he's procrastinated too long. He feels awkward and doesn't know how to move forward. I'm asking you to trust me. Trust Jess. And trust Luke's love for you. Don't give up too soon. Please mom. Don't give up on your dreams of happiness with Luke.

Jess sat staring at the paper, wondering. Who did she see? Some blank amorphous figure? Him? Crushing the brief flare of hope, he knew now what to add, and what he would say to Lorelai when he handed her the letter before going to Luke's.

Lorelai, years ago when I was the hoodlum you believed me to be, I know you saw the self help books in my bag. What you didn't know is they were Luke's books first. One of them came with a tape which talked you through realizing who you loved…"Whose phone calls or visits are never unwanted or too long? Do you see her face? Who would you most like to have in your life to ward off moments of loneliness? Do you see her face? …Whose face appears to you, my friend? Whose face?" Cheesy and as mockable as hell, but Luke listened to this and saw you. I know because he shoved the books into my hands and went straight to your house. To ask you out for the first time. It took him long enough, most of us recognized your connection right away. It's there, it's true and real. Now, knowing my Uncle the way I do, I think you should give him at least two weeks to process after I talk to him. He was planning your future and I think Rory is right. I think he lost his way and is floundering. I know he still sees your face.

"There, finished," Jess said as he pushed the letter to Rory for her to read.

"This is good Jess, but you have to make sure she reads it, wait till she's done. Tell her I made you wait. And you'll go soon?" Jess couldn't look away from her eyes as she pleaded. They shined a bottomless blue, and he knew he couldn't refuse her.

"Yeah. I'll go tomorrow." Jess agreed.

"Thank you! I have to go. Thank you Jess, I appreciate you doing this. I really do," Rory said as she hurried down the steps to the door. Jess followed, wishing there was something he could say to keep her with him. To keep her from walking out of his life again. Stopping in shock as she turned back to him at the entrance, his mind tricked him into believing for an instance he had spoken out loud, and his wish had come true.

"You didn't ask," she said, voice quiet. He could barely hear her over the hum of the air-conditioning. "You didn't ask me who I saw waiting for me, Jess. When I picture myself walking down the aisle, I see you. I always see you."

Jess thought his heart had stopped. He knew he needed to breathe, to respond. It was all he could do to keep standing, to not fall to his knees. He watched her push for a sad, wistful smile. It wasn't till the door had shut behind her that he found his voice, running to catch her, and seeing her cab pull away. His shouted "Rory" echoed around him as he turned back into the store.

"Are you okay?" Matt asked as Jess closed his eyes, trying to regain his equilibrium. He gave a quick nod before heading upstairs. Flipping open his phone, he dialed the printers he was using for his new book.

"Have you started printing yet? I want to change my dedication."