Disclaimer: Don't own Gilmore Girls, never have, never will…
Skylar and Jess started dating almost exactly one year after Rory and Dean started. The four of them became best friends. But Jess and Rory still had their own special connection. They hung out away from Dean and Skylar and they still even stayed over at each others houses, none the less in the same bed. It was something they had done from childhood and they couldn't break the habit.
The four of them did everything together. One night they all went to a party. When they arrived they were surrounded by familiar faces. Then the four of them went their separate ways to mingle with all the others they didn't spend so much time with. As the party went on they would meet up at times. Make sure everything was going okay, and then split up again.
While Skylar was waiting in line for the bathroom Rory spotted her and made her way over, "Hey, long line going on here."
"Yeah tell me about it, it hasn't moved in the last 15 minutes" Skylar started to whine.
"Well what do you expect?" Rory looked around at the others, "So are you having fun?"
"Hell yeah, we always have fun when it's the four of us".
"True, true" Rory looked over at Dean and Jess, "They seem to be enjoying themselves".
Skylar laughed, "Yep, them and their damn drinking games", she paused before she spoke up again, "you know sometimes I think they are playing for a reason, you know a male grudge thing… over you".
Rory gave her a shocked look, "What do you mean?"
"Well you know, Jess is your best friend, you guys have known each other WAY before Dean and I came along, he's very protective of you, and well, Dean being your boyfriend and all gets a little worried sometimes, that maybe Jess means more to you… he feels threatened sometimes, you know?"
Rory looked up at her, "They aren't fighting over me, Jess is like my brother and Dean has nothing to worry about, he knows that".
"Are you sure?" Skylar asked.
Rory stood there thinking to herself that there was no way that was true, "Well do you ever feel threatened by me? I mean you go through the same thing Dean does".
Skylar thought about it for a minute, "you know… sometimes I do, Jess drops anything in second if it has to do with you, and that doesn't always leave me feeling my best"
"I'm sorry" Rory didn't know what to say, "But you know you don't have to worry right? We're just friends" she assured her.
"Yeah I know" Skylar responded a little doubt in her voice.
"Jess really loves you, he doesn't let a day go by without telling me so, I've known him for a long time, and I've never seen him happier then when he's with you. He loves you so much, since the first time he laid eyes on you that night, he told me so even then"
"Yeah?" Skylar smiled, "I never knew that, I mean he's told me he loves me, but I never knew he said so the first night I saw him"
"Yep, it's true… you had him since the second you stepped foot in this town"
"Good to know" Skylar smiled.
The line finally started moving, "Find me when your done" Rory said as she began walking towards the boys.
"Boys, Boys what's going on over here?" she looked at them and they both froze, "Drinking games and you didn't even invite me to play? Shame" she smiled.
"Sit down and join us" Dean moved over so she could sit next to him.
"No its okay I'll just watch, its no fun when you join in the middle" She sat down and gave him a kiss, the truth was, she wasn't a huge drinker.
An hour later Dean was wasted and Jess was barely even phased. Skylar was with Dean on the couch, they both needed to sit for a minute.
"So Rory, you slept with Dean you little slut" Jess hit her softly on the arm.
"How do you know that?" she pushed him hard.
"Well let's just say Dean can't keep a secret when he's drunk" Jess laughed and pulled her into a hug.
Rory started to turn red; she couldn't believe he told. She looked up at Jess who had a smile on his face.
"You know I thought you would have told me" he looked her in the eyes and took a step back, "I thought we didn't keep secrets from one another"
She put her hands on his arms and rubbed them before taking his hands, "I know, and trust me I wanted to tell you but I didn't know how, it was a first, and besides you slept with Skylar and didn't tell me!" she retorted, and pushed him back once again.
"How did you know that?" he asked.
"Let's just say Skylar can't keep a secret when she's drunk" she laughed back at him.
"It's weird you know, I know we were never together, but I thought you would have been my first, you were my first everything, I thought it would be another thing to add to our list."
"Yeah I know, I always thought that too, but I guess times change and other people come along"
"A part of me wishes it would have been you."
Rory looked at him confused, "but it's best to be with someone you love."
"I know, but I wish it could have been something we shared together, don't get me wrong I love you, but only as a friend, nothing more, and besides I love Skylar and it was perfect. I couldn't have asked for it to be any better... Honestly I wouldn't change it for anything."
"Ditto" she smiled a small smile.
"We better get them home" Jess pointed to Dean and Skylar who were passed out on the couch, the conversation becoming weird for both of them.
"Good idea" Rory smiled as they made their way over to them, "you staying over tonight?" she looked at him.
"Do you even have to ask?" he smiled.
After they dropped the two drunks off at their homes they made their way back over to Rory's. They both lay in bed, neither saying a word, still unsure about the conversation they had earlier. But then Rory remembered what Skylar had said.
"Jess, you still awake?"
"Mmmhmmm" he said tiredly.
"When Dean and you have your drinking spats, are you really playing about something or is just fun and games?"
"What do you mean?" he asked rather curious now.
"I mean… I don't know… earlier at that party I was talking to Skylar and she said that she thinks Dean and you are fighting over me, that she feels threatened by me sometimes. Is it true? I mean the Dean and you grudge thing?"
Jess was silent; he wasn't sure how to respond. It was true, a part of him was jealous, and it was his way of getting over it, a simple drinking game never hurt anyone, but it was just protection like an older brother caring for his little sister, he had Skylar, he couldn't have them both, and he loved Skylar with all his heart.
"You don't have to worry about anything Ror. It's all just fun and games." He assured her even though it was a lie.
Rory turned over on her side so she was looking out her window. She was relieved that Skylar had been wrong. There was nothing to worry about, it was all just fun and games, but why did she wish it was more?
