Beginning is set during "The Incredible Sinking Lorelais" (season 4)

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"This is not a big deal. This happens to a lot of students."

"Okay…glad to be fitting in."

Rory slipped out of her professor's office and automatically headed towards her dorm, her head down. Unbidden, her eyes filled with tears and she angrily wiped them away. So stupid to be crying over something like this. She was angry, though. Logically, she knew her anger was 99% directed at herself and maybe 1% towards the professor, but she was sick and tired of being self-critical, so she imagined the professor's head on fire.

Fully immersed in her completely evil, yet incredibly satisfying fantasy, Rory started to unlock her dorm door when she heard loud voices.

"If he thinks it's okay to raid our communal mini-fridge, what's to stop him from crawling into bed with me or, god forbid, taking a shower with my soap? He'd crush me! He'd crush me all the way through the floor and into the goddamned foundation! And my soap would end up with little hairs – oh, Jesus Christ, that's a disgusting image." Paris. Rory could almost hear Janet rolling her eyes and Klees (what kind of name was that, anyway?) hulking in the background. Before Janet could shout a retort at Paris, Rory hurried around the corner and pulled out her phone.

"Hello, you've reached Lorelai Gilmore. Please leave a – " If it were possible to slam a phone shut like you could slam a door shut, Rory slammed the phone shut. The one time her mom didn't answer the phone. She'd answer when Rory wanted to complain about the lack of Cocoa Puffs in the cafeteria or the guy who kicked her chair in her poetry seminar, but everything starts to fall apart and Lorelai was nowhere to be found.

Tears pricked at Rory's eyes again and this time, she let them come. All her life, she'd had her mom to lean on, and even when they were fighting, she at least had Lane, or hell, anyone else in Stars Hollow to talk to. But Lane was gone now and that made Rory feel…unsafe. Unsupported. In high school, she'd always thought she was pretty independent. She took the bus by herself. After a couple speed bumps, she did all those mountains of Chilton homework on her own, no tutors, no nothing. She had boyfriends, a social life. But that first day at Yale, it had become achingly apparent just how dependent Rory was on her mother. They were each other's rocks.

Rory bit back a sob and tried dialing Lorelai again. No answer. She didn't know who else she could call in a situation like this…scrolling through her contacts, Rory bypassed Grandma and Grandpa (she absolutely did not want Richard to find out she'd had to drop a course – ugh, the mere thought of her failure made the tears run fresh). She skipped over Sookie's name. She was more her mom's friend than her own friend, and anyway, Sookie was really best at fixing problems to which the solution was pie or cookies or quiche. Christopher wasn't an option. Then she scrolled past Jess Mariano. She bit her lip as she stared at the name. A rush of emotions swept through her midsection.

The lights of the Festival twinkled in the background. Rory's face felt hot, but it wasn't from the bonfire.

"What do you have to say to me?" she demanded, staring at the boy who broke her heart.

Jess took a breath. "I love you," he said simply.

For a moment, the two just stared at one another, neither of them sure of what to say next. This situation felt horribly familiar to Rory. Another beautiful boy was telling her he loved her, and she had no idea what to say to him. Her feelings for Jess were so convoluted and twisted up; she hated him one minute and loved him the next. She opened her mouth slightly to say something – what, she wasn't sure – but Jess was already turning away. She watched him drive off in that old junk pile of a car and a tear rolled down her cheek. He ran away…again.

Rory hesitated only a moment before pressing CALL. She raised the phone to her ear with a shaking hand, half of her desperately hoping he wouldn't pick up or his phone had been disconnected.

"Hello?"

"Jess?"

"Rory?" He sounded incredulous.

"I didn't know who else to call," she said lamely.

"What's wrong?" Now he sounded worried. Or upset that she had called him. It was hard to tell when she couldn't see his expression. Her face felt hot and then she was crumbling.

"Everything's falling apart," she sobbed, choking on her own words.

"What's wrong?" Jess asked, more insistently this time. Rory snuffled unattractively.

"I just – Yale is harder than I thought it would be. I got a D on a paper and the professor said I should…I should drop the course…" she said, shaking her head and covering her mouth to hold back more sobs. "I feel like a failure."

"Rory Gilmore got a D on a paper? I don't believe it." She could almost hear the smirk on his face, the smirk she loved and hated.

"I went in there expecting a pat on the back and a 'well-done, Miss Gilmore,'" she continued, sniffling a little, and hating herself for it. She sounded utterly pathetic. She should just hang up now and cut her losses. He didn't want to listen to his ex-girlfriend cry. But she went on. "I've never gotten a D on a paper, ever. Well…there was that one time in high school…but that was high school. This is Yale. It's not supposed to be like this. I thought I was…I thought I was smart, I guess." She was rambling.

"Rory, stop," Jess said softly. The tone of his voice got her attention. "You are smart. And you're not a failure. Don't let anyone tell you different. I've never met another girl who reads as voraciously as you do, or knows as much about politics. That's pretty distinctly Rory Gilmore. That professor's an idiot. Just because he works at Yale doesn't mean he's the ruler of the world or has any say in what your future's gonna be like." She couldn't help but smile.

"Thanks, Jess," she said.

"I really believe all that," he replied. "I'm not just bullshitting. I swear." Rory laughed.

"I trust you," she said, and bit her lip. She'd said it flippantly, but the words made her think more seriously. Could she trust him? The boy who broke her heart?