Title: Chasing Jupiter

Summary: Extreme AU. He'd always been in love with Rory Gilmore. Little did he know that the woman he loved was also his best friend's fiancé. Rogan/Lit.

Background: Jess and Rory dated in high school until Jess left for California because he was failing. They did sleep together, around the time of Swan Song. Rory never slept with Dean. She is with Logan. Little does she know that Jess and Logan are best friends. The reason behind their being friends is explained in this chapter and in the next few. Rory and Logan began dating the same time during the show. However, as Jess is Logan's best friend, the Rory/Logan break-up played out differently than on the show. It will be explained throughout the first few chapters. Logan proposed, she accepted, and they are engaged. Lorelai and Luke are married. Christopher is the non-existent dad. Everything is pretty much the same. The story starts six months after Rory's graduation from Yale.

Rating: T – rating may rise. Be warned.

Disclaimer: I do not own Gilmore Girls.

--

She stared out the window, watching the summer sun make its way up and over the horizon line. She'd always loved this time of day – right when the sun was beginning to rise but hadn't quite yet. It was especially peaceful this morning, watching the sun rise above the California waves. No one but the birds and her to watch this.

Oh yeah… and Shira Huntzberger.

Rory sighed as she rested her forehead in her hand. Her soon-to-be mother-in-law was driving her absolutely crazy. No, no. Crazy wasn't the right word. Insane was a better description of how Rory was feeling at this moment. Shira Huntzberger had that effect on people.

"…I mean, doesn't that just sound perfect?" Pause. "Right, Rory?" Another pause. "Rory?"

Rory snapped to attention, realizing who was on the other end of the line. She tried to think of what Shira had been telling her, and found nothing. "Right." Shira squealed with excitement, and Rory suppressed a groan. What the hell had she just agreed to?

"Okay, well, I'm going to call Logan and tell him the plan," Shira told Rory excitedly, and Rory wracked her brain again, trying to remember what Shira had asked her. Nothing. Before she got a chance to ask Shira to clarify, precisely, what the plan was, though, Shira had hung up.

Rory rolled her eyes, flipping her phone shut and twisting the ring on her finger. It was a gorgeous ring, she had to admit. Logan had taste. A five-carat Cartier. She expected no less from Logan. He'd told her he'd had a problem deciding between a five-carat and a seven-carat. She'd fought the urge to roll her eyes in response to his dilemma. He knew she didn't want a big ring, or a big wedding, for that matter. But none of that mattered to his mother or her grandmother, who'd taken it upon themselves to make the Huntzberger-Gilmore wedding the biggest social event of the year.

Her mother had been the biggest surprise, aiding Shira and Emily in their efforts. Lorelai had called Rory several times to confirm and re-confirm the flowers, the dress, everything. And Rory had been left without an ally, a pal. She'd found herself a pit of wolves and the worst part was she'd thrown herself into the pit in the first place. Her only consolation (and a small consolation it was) was that Lorelai and Emily seemed to be getting along wonderfully.

She sighed when her phone rang again, half-expecting another round with Shira, or even her mother or grandmother. "Hello?" Despite her best efforts to sound cheery, she knew her voice sounded melancholy, and felt a twinge of sympathy for the person on the other end.

"Ace?" She smiled at the sound of Logan's voice. "Care to tell me why my mother just informed me that we're having three engagement parties in one week?" She frowned. That's what Shira had suggested. Damn.

"Oh, sorry," she told him. "She was just going on and on and I couldn't remember for the life of me what she was saying and before I knew what was going on she was asking me if that sounded perfect and I, of course, agreed and then she was talking about having to call you and tell you the plan and… sorry."

He chuckled on the other end. "No worries, Ace. Just try to not space out too much next time she calls, okay?"

"Okay," she responded, smiling slightly. "I promise to try. But beyond that, I can't promise anything else. You know how tired I'm getting of all these calls, though. Have you talked to your mom at all about this?"

"I did," he replied, but didn't elaborate.

Rory frowned. "And…?"

"And…" He sighed, and Rory's frown deepened. This was not good. "She told me that she wanted to be as involved as possible and I owed her."

"Because…?" she asked, curious and yet dreading what her mother-in-law-to-be told Logan.

"Because she wasn't invited to the initial bachelor/bachelorette parties and wasn't given a chance to stuff money in a man's underwear," Logan finished, chuckling.

Upon hearing his laugh, her frown quickly turned into a smile. "Please tell me you're not joking." Rory giggled. "And that you got that on tape."

"Unfortunately," he began. "I didn't. However, I have a feeling if we get a few shots in her at the second engagement party – which will be at the Ritz I believe – we may get a chance to hear it again."

"I'm in," she told him, and the two laughed at the thought of getting Shira Huntzberger drunk enough to say this again.

The two sat in silence on the phone. Each thinking about the other.

"I miss you," she admitted, blushing even though she knew he couldn't see her.

"I miss you, too, Ace," he said. "But I swear I'm bored here without you. My friend James isn't pleasant company."

"Ah, yes, James," she said. "Tell me why I haven't met him before?"

"Because every time I've had to come to Philadelphia you've had exams, or dress fittings, or newspaper articles due, and there was the one time when you were on the campaign trail that you…"

Rory sighed, smiling. "Okay, I get it. I'm a lousy girlfriend slash fiancé."

"Not lousy," he countered. "Just busy. Which is good. Can't have a lazy wife now, can I? Besides, you'll get to meet James this weekend."

"Which I'm very excited for," she told him proudly. "I can't believe I haven't met your best friend. He sounds like he's… well, no offense Logan, but your exact opposite. I'm quite curious as to how you two are friends."

"One of life's many mysteries," he said. "I think it's more because we relate more on an emotional level. He's had his fair share of heartbreaks and I have, as well."

"How cute," she cooed, giggling when she heard him groan. "Did you two eat ice cream and watch 'Terms of Endearment' together or something?"

He chuckled again. "Not really. He's just got a lot of girl problems. Apparently all stemming from some gal he met back in high school. She's been in and out of his life dragging him along. He just found out she's getting married, too."

"Oh wow," she commented. "That sucks. Poor kid. Did you buy him a pizza with everything and let him pick the movie?"

"Close," he said. "I took him out for beers and let him bash her for about an hour. He then took to his room. We haven't really talked about it since."

"So that's why you took the impromptu trip?" she asked. "Because of this girl that's got him all riled up?"

"Yeah," he replied. "He's been in love with the girl since he was seventeen. The last time he saw her, she kissed him and then decided she wanted to be with her dick of a boyfriend who apparently slept with a harem of other girls while they were still together."

She clicked her tongue. "That's rough."

"It's been a rough month for him," he said. "It was the least I could do for him. I figured we'd be up here anyway, so I surprised him by coming a few days early and spending some time with an old buddy."

Rory smiled. "You're such a good friend." A pause. "I can't wait to marry you."

"Ditto, Ace," Logan responded. "But listen, I really have to get going. James and I have to get out of here before my father realizes that I'm here, too."

"Okay," Rory said, laughing. "I love you."

"You, too, Ace," Logan said. "Bye."

She closed her phone and stared out into the morning. She couldn't believe how much she'd missed Logan since he'd left. And though she'd wanted to go with him, she knew she would have missed too much work. However, he had promised her that she would get to meet this elusive best friend of his that he always talked about. All she really knew about the guy was his name was James, and he and Logan had met when Logan was in California in high school. James was living with his father and working at a bookstore when Logan and his buddies had shown up – completely drunk – demanding to speak to Hemingway. James had apparently put Logan in his place, and the two had, somehow, been friends ever since.

Despite their differences, Logan and James were the best of friends. Rory recalled many nights when James had called Logan and the two had ended up meeting up the next morning for coffee or lunch. They never went out at night, as James now worked at a publishing house in Philly, and he didn't enjoy the idea of getting drunk. That was one thing she was thankful for, at least one of Logan's friends didn't enjoy the party scene.

She smiled, holding the phone in her hands. She needed to call Jess to let him know she would be visiting. Though they weren't together, she still enjoyed spending time with him and she really wanted him to finally get a chance to meet Logan. She dialed his number and put the phone to her ear.

"'Lo?"

"Jess?"

"Yeah?"

"Hey," she greeted, finally.

"Oh, hey, Ror," he greeted. "To what do I owe this pleasure?"

"Well, my fiancé and I are coming to Philadelphia," she explained. "And I really want you to meet him. Do you think you have time in that busy schedule of yours to pencil us in?"

"For you?" he asked. "Anything. How's Saturday morning for breakfast?"

"Sounds good," she replied. "I'll let him know."

"Okay," he said. "Listen, I'd love to talk, but I have to run. My friend's currently hiding from his father in the bathroom and we're trying to find a way out of this place without his dad realizing we're here."

"Have fun with that," she said. "Bye, Jess."

"Later."

She sighed and stood up to go and pack. Excited for the next few days. And meeting her fiancé's best friend.

--

"She's really great, James," Logan said. "I think you'll like her. She could give you a run for your money on books, too."

"Oh, a bookworm," James, or Jess, as he was referred to by everyone but his best friend Logan, commented. "And tell me why I've never met her before?"

"She's been busy," Logan replied. "She's either had exams, or we've been on a break, and there was the time she was on the Obama campaign trail. But you get to meet her in, oh, less than half an hour."

"Geez," Jess scoffed. "You're acting like a school girl. Calm down, Huntz."

"Can't," the fair-haired boy said. "I just… I can't believe how much I've missed her this week, you know? Love, my friend, is an amazing feeling."

"Unless, of course, you're feeling it for a girl who's already given her heart away," Jess replied.

"How is the ex?" Logan asked. "That was her you were talking to on the phone when I came out of the bathroom yesterday, I assume?"

The brunette nodded in response. "Yeah. She wants me to meet his dick of a fiancé of hers tomorrow morning. I swear, someone needs to get me checked for a psychological problem if I'm agreeing to shit like this."

"It won't be so bad," Logan said. "Hey, at least you're not in my boat."

"Worse?" Jess asked.

Logan shrugged. "Ace wants me to meet her ex. He's the one who got her to go back to school and wrote a book and—"

"Caused the great break up where you slept with the entire bridal party," Jess finished. "Nice job on that, by the way. But at least she came back to you. I drop out of school and this girl never gives me another chance. What does she do, though? Runs back into the arms of this prick even after he cheated on her while they were together."

"Life's rough," Logan told him.

"Agreed," Jess replied, resting his chin on his hand. The announcement came over the intercom that Logan's fiancé's plane was in, and the two made their way to the door to wait for her.

Logan scanned the crowd for Rory. He spotted her brunette head, looking around for him and smiled when their eyes connected. Jess followed Logan's pointing finger and nearly fell over where he was standing. Rory stood there, wide-eyed as the pair made their way over to her.

"Hey, Ace," Logan greeted, kissing her softly.

Rory forced smile, looking in confusion from Logan to Jess. "Hey, Logan. Uh… what…"

Jess raised his eyebrows. "I could say the same thing."

"Oh, how rude of me!" Logan exclaimed. "James, this is my fiancé, Rory Gilmore. Ace, meet my best friend James Mariano."