Since you had to wait two days after signing up before being able to post a story, I managed to finish chapter 2 of this story while I was waiting.
"So this is it, my home for the weekend." Jess sweeps his arm out, as to show her the hotel room.
"It's nice." She smiles, looking a bit nervous.
He starts helping her off with her coat.
"Do you want something to drink?", he asks while he puts away her coat. "Something without alcohol maybe, to wear the buzz off?", he whispers in her ear as he is walking by her.
She doesn't answer, instead she grabs his arm decidedly and pulls herself closer to him.
"Sorry", he holds his hand up in front of him as to excuse himself. "I can get something with alcohol in it, if it's that's important to you."
"Ssch!", she just says and puts her lips to his. A bit surprised, but pleased with the development he kisses her back.
He can't help it, nor explain it, but a warm fuzzy feeling takes over his whole being. He can't remember it ever feeling this good kissing another person. He wraps his arms around her and pulls her closer to him and deepens the kiss. He can't stop, he can't get enough. He can finally understand what people mean when they say 'I wish this moment could last forever', he had always thought it to be a cheesy line. But this. This moment. Kissing her. Kissing Rory.
Suddenly she pulls away from him, and for a few seconds they stand quiet, inches away, just staring at one another.
"I'm sorry, Jess", she says quietly and puts her hand up to her mouth, as if that was the only way to stop her lips from wanting more.
"Sorry about what?", he says and takes a few steps back. He stands there looking at her, with his guard up, reminding her so much of the 17-year old boy she loved all those years ago.
"I'm kind of still with Logan."
Jess sighs, starting to look irritated.
"Kind of? So what is this then? You kissing me, what is this? I don't deserve this Rory. I thought you… I thought we, finally…" His voice dies out and he just stands there, looking crushed.
She hesitates for a second, and starts rambling with an irritated voice.
"He cheats on me…not only with one bridesmaid, but with two, and then I'm not even counting the bridesmaid he just fooled around with. And still, I can't even kiss you without feeling guilty. I mean it's you. Jess. Not some random bridesmaid that I don't even like, that I make up names about, like 'Blondie or Dizzy'. I like you, Jess, I always liked you, you know that. I mean, I broke up with Dean to be with you, and Dean never cheated on me, still I left him heartbroken to be with you instead. So why can't I even kiss you without feeling guilty, huh? Why?"
She sinks down on the bed and bursts in to tears. Jess gently sits down on the bed besides her, he looks confused but decides he better pin out the details at a later time. Anyways, her outburst just now gave him enough info for the time being, apparently she's still with that Logan guy, that jerk with the Porsche, and apparently he turned out to be exactly the kind of jerk Jess had thought him to be on their first encounter. He puts his arm around her and starts talking in what he hopes is a comforting voice.
"You broke up with Dean to be with me, you didn't cheat on him. It's not who you are, you don't cheat, you don't lie and most of the time you go out of your way trying not to hurt the people around you. You're a good girl Rory Gilmore. No, in fact, you're a great girl, and if that stuck up, rich little brat can't see that, it's his loss, right?"
"But you're right. You don't deserve this. It's so unfair of me to drag you in to this mess. I just… It felt so good seeing you there, at the pub."
Jess puts his arms on her shoulders and forces her to meet his eyes.
"Do you love him?"
She tries to avoid the eye contact, but his grip around her shoulders is steady and almost as desperate as the look in his eyes.
"Maybe. I don't know. I thought I did, before."
"You thought you did before this, before the bridesmaids?"
"Before the bridesmaids, before seeing you at the pub, I don't know. My heart literally skipped a beat when I saw you, your heart shouldn't skip for anyone else when you're in love. I mean, yes, we have history together you and I, but still, even for history, your heart shouldn't skip a beat. My heart doesn't skip a beat when I see Dean, and we have history together, not that I've seen him in a long time. Maybe now my heart would skip a beat for him as well, maybe I developed a condition: a skipping heart condition. Maybe I'll have to move and join a convent, so that my heart can have a normal rhythm; a non-skipping rhythm. And, in a convent you're not allowed to have boyfriends, so there's no risk of your boyfriend cheating on you with bridesmaids. Do they allow bridesmaids in a convent? I would like to continue my studies; do they let you study in a convent? Do you think there any convents near Yale?"
"Hey, hey! Calm down. Maybe the convent can wait until tomorrow? Don't think they would let you in a convent in this intoxicated state anyways, so why don't you sleep it off, and if you're still set on joining a convent tomorrow, I'll drive your there myself."
"I am actually pretty tired."
"There you go. Make yourself comfortable, I'll go get you a glass of water."
Rory crawls down under the cover, when she hears Jess coming back into the room she quickly wipes some tears away from her face and smiles at him.
"Thank you for taking care of me."
He puts the glass of water down besides her on the bedside table.
"Anytime."
"Jess… if I had gone away with you when you asked me, you would never have slept with a pack of bimbo bridesmaids, would you?
How could this guy do this to her? To Rory, the most caring and loving person he'd ever met, how could he treat her like this? Hurt her like this? He himself would probably not have won the boyfriend of the year award back when he was with Rory, but he never intentionally hurt her, he never cheated on her. Yes, he did leave her, and yes he broke her heart, but that was only because he didn't want to drag her into the big pile of mess that he was back then. He thought she'd be better off without him.
He tries to smile when he answers her.
"Well, bimbos never really been my thing you know, but I guess we will never know what would have happened, will we? Try to get some sleep now, and we'll talk more tomorrow, when there's actually a chance that you'll remember the conversation." He says while tucking her in and kissing her forehead.
"You wouldn't have, I know you wouldn't", she mumbles, half asleep already.
Jess gets up from the bed and sits down in an armchair at the other end of the hotel room. He is too agitated to sleep. He had thought about searching her up, in fact that was the reason he had insisted on going to New Haven on this book tour of theirs, although he told his co-workers it was because he thought their books would be better received here, in a college town, than in New York; competing with every other up and rising author.
But he had been afraid of what he might find, afraid that she had continued on the road she was heading down last time they met, afraid that she had turned into her grandmother: a society wife, giving cocktail parties and attending functions. But, other than the cheating boyfriend, she seemed to have gotten her life pretty much back in order since then.
Now she was the editor of the Yale Daily News. He was proud of her, she might have hit a bump or two in the road, but she was certainly back where she belonged. Truth to be told, the bumps in the road probably made him like her even more, if that was even possible, it showed that she was no more than human herself, capable of making mistakes. He figured that's why he gotten so angry at her during his last visit, all the time they where apart he had been putting her up on a pedestal, deemed her incapable of making mistakes.
He makes himself comfortable in the chair, pulls a blanket over himself and lets his mind wander off through all the "ifs" consistent throughout his history with Rory. At last he falls asleep, with a faint smile on his lips.