DISCLAIMER: Hmm, no Gilmore Girls here! But I do own Milo Ventimilgia, it's amazing what you can find at Wal*Mart these days...

RATING: PG, I guess, for mild language...very mild. Lol.

AN: Ok, this is just a one parter set after They Shoot Gilmores, Don't They? Jess has already broken up with Shane, the Dance Marathon just happened, and Jess and Rory are on the bridge. I'm still putting my heart and soul into Lilacs, but it's giving me trouble, and this idea hit me, so I ran with it. I would really appreciate feedback, I love writing, but I also love to know how I'm doing. I know this isn't my best, I hope I didn't come off too trashy romance novel...

Could, Should, and Would---

Jess Mariano never belonged in Stars Hollow. Hey, he knew it the moment he stepped off the freaking bus! Yet here he was, trying to believe the person naive enough to think he had a place in this screwed up hiccup of a town. She was the only one to offer a reason to try.

She was beautiful. Yet he caused her pain. And he hated himself for it. No, he didn't control Dean into breaking up with her. But he drove him to it. It wasn't like he planned it out... Rory Gilmore intrigued him. It was new; most girls were a hobby, like Shane. Being why he was no longer with Shane.

And suddenly, she took notice of the boy watching her tentatively in the shadows, afraid to disturb her. As she turned, he saw the tears cascading down those porcelain cheeks. He couldn't help the sudden urge to wipe them away, to hold her and reassure her. What was happening to him? He was turning into some nitwit Romeo!

"Go away Jess." Classic.

"Funny, last I heard, this was public property. Unless Taylor went on some mad bridge-buying binge," he said, settling down beside her.

"Jess...not now. Dean...it's over. It...it can't, I mean..."

"Shh. Dean's an idiot. He let you go, there's no way you can tell me he's got a full set of brain cells now."

"Shut up! Dean was a perfect boyfriend! He was nice, polite, he cares about me..."

"Which all nicely explains why you kissed me, right?"

"What? I can't believe you! I slipped! That's all! SLIPPED!

"Yeah, slipped right on my lips."

"Unbelievable!"

"Relax, it was a nice kiss. I've missed it."

"Really? I would imagine that bimbo you literally immerse yourself in would have satisfied your 'thirst'!"

"I broke up with Shane."

"Oh... Oh."

"Yeah." Awkward silence. Funny, that wasn't normally a problem. But how do you evolve what they had? So, she spoke up.

"So what now? I mean, do you... wanna...bewithme..." those last words came out in a jumble, she had to struggle to recover, while he looked on, slightly amused.

"Or not, that was stupid, we could be friends, we should be friends, or we..."

"Ror, stop, seriously, before you choke on your words."

"So... that's a..."

"I wanna be with you."

"Oh... good."

And for a while they sat there, taking in the comfort of the other's presence. Pondering what was at last a possibility. "We can't do the Rory."

"What? Why? Jess, stop, I can't take this!"

"It's just...I don't want to hurt you."

"So don't!"

"It's not all black and white, ok? And you're the only freaking one that can't see that! Ask anyone here, ask your mom, I'm sure she'd love to tell you 'us' can't work!"

"Us involves me too Jess! I say we can work! Give them time, they can adjust. It's not about what they think! Why should they hate us for being happy?"

"Well, my name's not Dean, for starters!"

At this she paused. Of course. Dean was accepted; therefore, he had permission to come a courtin', so to speak. Rory just closed her eyes with a deep breath.

"A name. What is in a name? For that by which we call a rose by any other name would smell as sweet."

"You know, you're cute when you quote, in a Brady Bunch kinda way."

"Jess Mariano, did you just call me sappy?"

"Hmm... sappy? I don't recall that term being used..."

"You're mocking me!"

"Never!" He smirked as she hit his shoulder playfully with the back of her hand. The banter ended and was replaced with a thoughtful silence. Could they ever dare to just stop thinking?

And then he just stood up. He started to walk away, but against all better judgment, he turned around, complying with that naive little part of him that wanted nothing more than to hold her tight for eternity. That little part was foreign to him, he hated being such a romantic idiot. So he just held out his hand to her. She shouldn't take it... but he had to give her a choice.

Rory knew the risks. She knew it was utterly impossible for them to get through this in one piece. But you know what, screw logic! Screw thinking! Gah, she was so bad at this. Freaking hereditary anti- relationship skills! She made a mental note to herself to scream at her mom later for passing down her lack of ability to her. But for now... Jess was proposing a risk. Rory always played it safe. She never took a risk beyond red nail polish!

But that WAS her hand reaching for his. And those WERE her feet, walking away with him.

So risk she did.

And it was beautiful.