It's been five weeks since Sam met Jessica Moore. How Brady succeeded in dragging him out to that frat party, he no longer remembers, because the arguments he used aren't as important as the fact that Sam met Jess and now she never leaves his head.
After the first week passed, he started adjusting the bike routes that he took to and from his classes, just to ride past the Kappa Kappa Gamma house and see if he could catch a glimpse of her smile or her brilliant blue eyes. Sam dreams about her sometimes, about holding hands and making out in the back row of the vintage theatre that shows the old movies and fingering her yellow hair on the nearby playground's swings and fucking her at midnight behind the rosebushes in her house's backyard. He knows that he could ask her out. No other girl has caught his eye like this before, and for once, Dean and Dad aren't around to ruin it, to pull him off for no reason he can explain or put him in tight spot after tight spot or just make obvious the fact that, underneath his textbooks and carefully crafted college boy facade, Sam will always be a freak. He could make the final break with them, and the thought makes his stomach twist in longing.
But every time he's ridden past her house and seen her — on the lawn, throwing water balloons with her friends; or in the driveway, polishing her candy apple red Schwinn (which, besides the care she's given it, is clearly new — one of last year's present, or so he's heard, from her father — and makes his second-hand model feel that much more rickety, and reminds him that Dad most likely stole his bike); or in her window, when she's changing — Sam feels his throat coat up like it's full of peanut butter and anything that he could say sounds stupid. Besides, a girl like her would never like a guy like him.
Today as he passes, en route (ostensibly, if anybody thinks to ask) to go buy bread and lunchmeat, she's out on the driveway once again — blonde hair tied back in a ponytail, in flip-flops, a t-shirt, and pink workout shorts, cleaning dirt that isn't there off of her bicycle. As he nears her place, he slows and a smile ghosts across his face. A breeze rolls through, knocking some of the fire-red leaves off the tree that overlooks Kappa Kappa Gamma, and they tumble around her feet. Even if he can't ever ask Jessica Moore out, he can look at her, can't he?
Looking over her shoulder, she wrinkles her nose at him and calls out, "Hey, you!" ...Shit. Sam's face flushes bright red — she's seen him, and she's probably seen him before now too. Going away is the only option; maybe, if he gets away, it'll all blow over, and she'll just forget him and get on with her life untouched by him. He keeps riding until she adds on, "Sam!"
Even if someone else rode it before he did, Sam turns his bike around on a dime and stops it in her driveway. "...Hey, Jess," he sighs, affecting a broad, awkward smile.
"Don't you, 'Hey, Jess' me, Winchester." Putting down the kickstand, she approaches and, even though he's taller than her, when she puts her hands on her hips and glares up at him, Sam feels so much smaller than he is. "Do you think I haven't seen you riding by here? Every day? For a month?"
"Well, no — I mean, I—"
"Or looking in my window?"
"Jess, it's not like that—"
"Well, what is it like, Sam?" she demands; she crosses her arms underneath her breasts and, against his better instinct, Sam looks down. He blushes bright red when, expectantly, she clears her throat. "I'm waiting, Sasquatch."
Sam swallows thickly. Closing his eyes, he splutters: "I'm-really-sorry-Jess-I-didn't-mean-to-creep-you-out-I-just-think-you're-nice-and-smart-and-pretty-and-I-couldn't-bring-myself-to—"
Standing on the tips of her toes, she cuts him off with a kiss. Holding onto his wrist, she whispers, "They're showing Casablanca at that place in town. Pick me up at seven?"