Jess is the only Milo character i didn't like. I really don't like bad boys 😂 Why are ppl so obsessed with them i'll never know. Their bad boy fantasies made Damon and DE something they're not and killed SE
Yeah Jess was my Damon then I got over it. Like being 13 I thought he was cute and I thought he was smart and well-read buy he had an edge and it was cute basically everything Lorelai says to Rory about guys like Jess and it took me a while to let go of the nostalgia but when I finally did I was like yeah he treated her like shit and him popping up every so often with one sentence wisdom that for some reason transforms Rory’s life didn’t make me side eye him any less
Rory drops her legs down over the edge of the bridge and Jess settles beside her, brushing her ankle with his.
“Sorry,” he says and Rory smiles, looking away.
“Well,” Jess says, leaning back. “It’s been a long time since we were out here.”
“More than ten years.”
“I loved it here. It was so away from everything.”
“Not just because Luke pushed you in?” Rory teases and Jess laughs, shaking his head.
“That was just a bonus.”
Rory laughs too and Jess glances at her.
“I liked sitting here with you.”
“Yeah,” Rory says quietly. “Me too.”
They sit in silence for a moment and, wordlessly, Jess pulls out a bottle of wine from his bag and unscrews it, handing it to Rory.
“Jess,” Rory exclaims. “Where did you get that?”
“From my apartment! Relax, I didn’t take it from Doose’s, though the thought of upsetting Taylor isn’t entirely unappealing.”
“I’m sure there’s some law against drinking out here.”
“Relax, Rory. They won’t arrest us for a sip of wine.”
Rory pauses for a moment before taking it. She holds the bottle up, hesitates, and then takes a large drink, laughing as she hands it back to Jess.
“Cheers,” Jess says, matching her grin, and takes an equally large gulp himself. Putting the bottle on the deck, he leans back on his elbows and Rory lies down on the wood.
“God,” she says. “It’s been so long since…..”
Jess waits but she doesn’t go on and he prompts,
“Since I did something like this,” Rory says, sitting up. “Since I wasn’t working or making time to see Mom or helping with Grandpa’s -” her voice catches but she steadies herself and says quietly, “It’s been a long time since I did something like this. Something dumb and fun.”
“It’s not dumb, Rory.”
Rory gives him a look and Jess chuckles.
“Okay, but it’s dumb in a good way, right?”
“I’ve missed it,” Rory admits. “Everything’s been such a crazy blur lately.”
She sounds sad but simply says,
“We did dumb stuff like this all the time.”
“Yeah, we did.”
“Minus the drinking though.”
“Well, I did try and grab a beer from your mom’s that time, but she busted me for it.”
“Right,” Rory laughs. “And you asked me to bail.”
“It was so long ago.”
“It was at that.”
“We were such kids,” Rory exclaims, staring up at the sky. “It just seems - how can it have been so long? It doesn’t seem that long since we’d sit here or watch a movie or annoy Mom or Luke and now -”
“I know. We’re still us, Rory.”
“And we’re out here on our bridge,” Rory says, finishing the thought, and Jess stares into her eyes, his heart leaping at our.
“We certainly are.”
Rory sits up, lean over and grasps Jess’s hand tightly and, without a single word, Jess holds it tight. They can sit until morning.