Disclaimer: I own nothing. Taken from the episode where Jess is told he's not graduating (don't remember which one that is).
Jess knocked on the principal's door. "Come in!" the principal called. Jess complied.
The principal's eyebrows raised in surprise at Jess. "Well, well. Jess Mariano. What a pleasure."
Jess could have sworn that the principal was hiding a triumphant smile. He'd thought Jess had finally come to him for help.
"Sit down." the principal said. He moved toward his seat.
Instead of sitting, Jess said, confused, "I was just trying to buy prom tickets and they told me to go see you."
"Sit down." the principal repeated.
Jess shrugged and sat down. He could at least humor the principal until he got to the bottom of the matter.
Once Jess was seated, the principal continued. "So the prom, huh?" he said, "I wouldn't have taken you for someone who would want to go to the prom."
"My girlfriend wants to." Jess clarified.
"That's too bad." the principal shook his head.
"What? Why?" Jess leaned forward in his seat. What did he mean, Jess couldn't go to the prom?
"Because you flunked out." the principal said flatly.
"I what?" Jess raised his eyebrows disbelievingly.
"You're not graduating, Jess." the principal said. "Prom tickets are for graduating seniors only." he said, putting emphasis on 'only.' "Guess your girlfriend's out of luck."
"Now, wait a minute--" Jess tried to cajole the principal. "I'm just a little behind. I can catch up--no sweat!"
"No you can't. You missed too much."
"It hasn't been that much!" Jess insisted.
"Thirty-one days you've been out--cutoff is twenty."
The confidence left Jess's voice and gave way to defensiveness. "So that's it--just like that!"
"That's it."
"Thanks for the warning." Jess said sarcastically.
"You mean the nine warnings we gave you weren't enough?" the principal challenged. "All the meetings I tried to set up between you and your guidance counselor--between you and me--that you blew off. That wasn't enough?"
"I can catch up--I'm smarter than anyone else here."
"And humble, too." the principal observed.
"I can catch up!" Jess repeated. "You'll see."
"There's nothing to see." the principal said. "You're out."
"Fine!" Jess said. Then a new idea popped into his brain. "I'll take summer school if that's what you want." he offered.
"Good," the principal conceeded, "but it's not enough. You have to take the whole year over."
"The whole year--no way!"
"Then no diploma."
Jess slumped in his chair. "At least let me go to the prom." he almost pleaded. "What's the big deal?"
"We're done here." was all the principal said.
"Come on!" Jess cajoled.
"You want to talk about coming back next year--my door is open."
Jess rose from his chair. What was he going to tell Rory? Would she even want to talk to him after he told her? He decided as he walked to the door that he wouldn't tell her.
"I'm not going to miss this place." he told the principal as he left.
"Vice versa." the principal said without looking up from the document he was reading.
As Jess went to the diner, he formed a plan. He would go to California, to see his dad. He collected his stuff, left a note for Luke explaining why he was leaving but not where he was going, hopped the first bus out of the small town of Stars Hollow, and never looked back.