After leaving the school they went back to Stars Hollow for her graduation party. After a few hours Rory told her mom that she was tired and was going to go home. She insisted that her mom stay and have fun and that she would be fine alone. So Rory headed home in the dark, but as she got closer she took a different turn and headed to the bridge. When she got there, she saw an all too familiar figure sitting there smoking a cigarette in an all too familiar way.
"Jess? What in the world are you doing back here?" she asked, approaching him.
"Nice to see you too," he answered.
"Where were you when you called this afternoon?" she continued, sitting across from him.
"Bus," he replied, putting out the cigarette.
"Why didn't you stay? You know I wouldn't have been mad at you. Okay, maybe a little, but I'd get over it. I just want to know why. What happened? You could have quit your job at Wal-Mart. You didn't really need a second job anyway," Rory rambled.
"You don't need me Rory, your going to Yale this fall. You'll meet a prestigious guy, fall in love and have little Ivy League babies and live happily ever after. I'll be the guy stocking the shelves at the stores you're to rich to go to. You deserve someone else Rory," he spat out.
"Ivy League babies?" Rory looked like she was trying not to laugh.
"Yeah," Jess realized how stupid it sounded too.
"Jess, you know that's not me. Since when have I ever cared about stuff like that? I like Wal-Mart, if you ask nice enough they'll give you a smiley face sticker too," she stated.
"You never answered my questions," she said after a pause.
"The ones about school and the second job?" he asked.
"Yeah," she said in Jess' monosyllabic tone.
"You know I've never liked school. Everyone's so stupid. It's all about the jocks and the popular kids. All it is is a freak show," he said.
"That still doesn't explain the second job. I mean, what could you have possibly needed that cost so much money you and Luke together couldn't afford it?" she asked.
He didn't say anything. He just pulled out a small box and handed it to her.
"What's this?" she stared down at the dark blue box.
"I had it all planned out Rory. I was going to make you proud of me. I was going to graduate and take you to the prom and then I was going to go to your graduation. I had a whole plan for tonight Ror'. I've had it planned for months. I was going to take you out and afterwards I was going to take you to the bridge and tell you that I loved you and then I was going to give that to you. I needed a job so I could afford it. I thought I had it all worked out, but then the principal said I'd skipped too much school to graduate. I was going to school, I wasn't cutting as many classes, I wanted to prove to you I could do it," Jess explained.
Rory was rather shocked at his admission and by the fact that he had said so much.
"What made you think you had to prove yourself to me? I figured you already knew how I felt about you Jess. And I don't care if you have to go back to school and if you go back to school that would prove a lot. Not that you need to prove yourself, I'm just saying that if you had to, which you don't, it would be a very good way," she answered.
"You gonna open it or what?" Jess pointed to the box, not wanting to talk anymore.
"Oh … sure," she said, lifting the lid.
Rory looked at the box's content and back at Jess. She wondered if her assumptions were right. Could Jess really be embarrassed? Or was it nervousness? She wasn't quite sure.
"I know were not together anymore, but I still want you to have it," Jess finally said.
"Was this my graduation present?" she asked.
"No," he said.
"Not that you were supposed to get me a graduation present, but if it's not then what is it for?" Rory questioned.
"It was for when you went off to Yale and I was going to be stuck here in this stupid town. It was supposed to be a promise ring. Don't think I'm turning into some freaking romantic or anything, I just didn't want all those guys at school to think you were available or anything," replied Jess.
"Oh," Rory said, sounding like Jess again.
"I still don't get why you left though," Rory said after a long few moments of silence.
"I don't know Rory. It's just that my dad was back and it seemed like a good opportunity and everything was messed up. So, why not? I figured you'd want to be free to date whoever you wanted to in college, not be stuck with a bad boy here in Stars Hollow repeating the twelfth grade," he said bitterly.
"Huh," she said, sounding more and more like Jess.
"I figured that since no one knew me in California I wouldn't be such a disappointment to everyone, but man you should see what living with dad's like," Jess said.
"What's it like?" Rory asked, breaking from her monosyllabic sentences.
"Their place is okay, my dad is too, but his girlfriend is messed up. I mean she seems okay at first, but she's like the female version of Kirk and her daughter hides in the cupboard all day," Jess stated.
"Sounds like they belong in Stars Hollow more than we do," she laughed.
"Yeah," Jess said, resuming his monosyllabic tendencies.
"Jess," Rory said.
"Huh?" he replied.
"You were right. What you said about me wanting to date whoever I wanted in college, that was true. That whoever was you. You were wrong Jess and I thought you knew me well enough to know that," she admitted.
Jess didn't say anything.
"I still want to be your girlfriend Jess," she said.
"We never broke up in the first place," he pointed out.
"Huh," she mimicked him.
"But you can't do this anymore Jess. You can't just leave me whenever you assume I'm going to do something. Got it?" she said firmly.
He nodded.
"So, now what?" she asked, feeling awkward.
"Come here," he took her hand and led her away from the bridge, taking the box back from her in the process.
"Where are we going?" she asked, following obediently.
"Pretend I never left. Pretend that we just got back from dinner and a movie and that we left the party at Luke's and that we just walked here," he commanded, putting the box I his coat pocket.
"Okay," she said, slightly confused.
He put his arm around her back like he always did and started walking back to the bridge.
"So did you have a good time tonight?" he asked her, hoping she would play along.
She hesitated a moment and then went along with it.
"Oh, yes, but I'm glad we decided to leave the party since mom got out all my baby pictures," she said.
"Sit down Rory, I want to tell you something," he said when they got to the end of the bridge.
"Okay," she sat down with him.
"I know your going off to college and everything, but I still want us to be together," he started, obviously he had this planned.
"I want us to be together too," she replied.
"I love you Rory," he said sincerely.
"I love you too Jess," she said quietly.
"I got a job at Wal-Mart so I could buy you this," he opened the box he had given her earlier.
"Jess-" she started, knowing this is how he wanted the night to have been.
"It's a promise ring. I know it sounds really dumb, but I don't want any guy to get any idea that your available," he explained as if it were the first time he had told her this.
"It's beautiful," she commented as he put the silver ring with her birthstone on it on her right ring finger.
"I hope you're not upset that I didn't graduate. I wasn't slacking off anymore, but I missed too much at the beginning of the year. I'm going to go back though, I'm gonna graduate," he said, not pretending anymore.
"I'm not pretending anymore Rory," he said.
"I know," she said, leaning over to kiss him.
"I'm proud of you Jess," she told him after they kissed.
"I'm proud of you too," he replied.
"Let's go back to my house," she said, standing up.
