The first time Sam Winchester fell in love, he was seven years old.

Her name was Elisabeth Saunders, and she was, without a doubt, the cutest girl in his second-grade class. At first Sam had been reluctant to make any friends in this new Missouri town – he'd really liked their last house, being back in Kansas for a little while; even if he didn't remember it, that's where he was born, and he wasn't happy about having to move again – but the moment he laid eyes on Elisabeth, he changed his opinion. Of course, that didn't mean he made friends instantly. Sammy Winchester was actually really nice, or at least he thought so, but he didn't make friends easily. Dad said it was probably because he was smart and shy, which put people off. Dean snorted and muttered that it was because Sammy was to smart for his own good and downright obnoxious to top it off.

Even with Elisabeth Saunders in the equation, Sam wasn't sure about the whole new friends thing. But he couldn't just walk up to the girl herself without support, so he resigned himself to making a new impression on his classmates. He started talking to Kenny Holdsworth and Jason Morgan, and after a while, he came to call them friends. They were playing video games at Kenny's house when Sam worked up the nerve to ask them about Elisabeth.

"Girls? Ick," Kenny replied, mashing a few more buttons in an attempt to fend off an oncoming horde of aliens. Sam sighed; Kenny was in the camp that clung firmly to the belief that girls had cooties and would have nothing to do with them.

"I dunno, Sammy," Jason said, stretching lazily. "I think she likes Tyler Wind." Sam struggled to remember who Tyler was, and grimaced as he pictured Tyler's spiky, gelled blonde hair, big blue eyes, and "adorable" (or so he'd heard it described) smattering of freckles across his nose. Sam, awkwardly tall for his age, with floppy hair that fell more in the "unkempt" range rather than the cute puppy look, and his general lack of people skills, was no match for Tyler in a competition for a girl's attention.

"Good choice, though," Jason congratulated him approvingly. "Lissy's pretty cute."

After more alien-smashing, Sam went home, feeling very depressed. It appeared that his first ever love campaign would be over before it began.

Dad was at work – regular work, not the supernatural-beasty-hunting kind – so Sam dejectedly sat at the kitchen counter in their tiny, two-bedroom apartment and poured himself a bowl of cereal. Morosely, he swirled the cereal around in the bowl with a spoon. He'd checked in the fridge for milk, but the bottle they had was two weeks past its sell-by date. Sam had sniffed it hopefully, but after he almost puked from the smell, he decided he was better off without it. If you can eat the milk, you shouldn't, Dean always said.

Speaking of Dean. Sammy raised his head, searching for his brother. Dad would never leave him home alone for long without Dean there to babysit him, despite the fact that Sam thought he was well capable of fending for himself by now, but he hadn't heard a peep from the bedroom they shared. "Dean?" he called.

"Mmrf," Dean replied, which Sam took to be a muffled "shut your cake hole, I'm sleeping." He didn't particularly care, though. Dean, at age eleven, had just reached his two-week anniversary with his first girlfriend, and Sammy wondered if maybe his big brother could give him tips on how to win over Elisabeth. He wasn't quite ready to give up on her yet, he realized, and Dean just might have the answers.

(It would be many years and many violently awkward situations later that Sam finally learned not to ask his brother for dating advice, but for now, he was clueless and Dean was somewhat innocent, or at least for Dean Winchester he was innocent, and so it would take a while for Sammy to discover that Dean was really not the right guy to ask for help on these occasions.)

Sam padded almost silently to their bedroom and peeked in the door. Dean lay sprawled across his bed, which was the bottom bunk (Sam still didn't understand why he, as the younger brother, was expected to sleep on top, but again, this was before he discovered lots of things about his brother, such as Dean's fear of heights – it wasn't a fear of heights, Dean always argued; it was a fear of falling, which was perfectly rational – but again, at seven, Sammy rarely thought to question his brother's motives) with a car magazine next to him. He blinked sleepily at Sam and asked, "Humnerhuf?"

"You really need to learn not to make up languages when you're sleepy," Sam admonished, only half-joking.

"Shut up, Sammy," Dean mumbled, which was really the only English phrase he could enunciate clearly in his sleep. Well, that, and something about pie.

"Dean," Sam began tentatively, "you… you really like Annie, right? Like, you like like her?"

Dean glared. "You're really not going to let me sleep, are you, kid?" he complained, but he sat up anyway. "Of course I like her, weirdo. She's my girlfriend."

"Have you kissed her?" Sam asked curiously. He didn't think he was interested in doing that with Elisabeth yet, no matter how much he liked her; he found the very idea of kissing kind of gross, actually. Spit exchange? Eww. No thanks.

Dean colored. "What? No!" (Innocent still, remember. In the future, Sam would tease him mercilessly about this moment.)

Not wanting to annoy his brother before he'd even gotten to the point of the conversation Sam quickly backpedaled. "Well, I mean, it's just, you're dating, so…"

"Ugh, Sammy, just shut up!" Dean was still bright red, so he pulled a classic Dean Winchester move: he went to deflect the attention from himself. "Why? Why's it matter to you?"

"Well," Sam said hesitantly, "there… there's this girl."

Dean snorted. "Of course there's a girl. Jeez, I didn't think I'd have to have The Talk with a seven-year-old, but then, you always were precocious."

Sammy hurried to head off that discussion, having heard terrible things about The Talk from his peers in school. "No, no. I mean, she's…" He tried to think of a way to describe the girl of his dreams. "She's Elisabeth," he said finally, as if that explained everything.

Dean rolled his eyes. "Okay, so what is it exactly that you want, Sam?"

Sam blinked; he hadn't considered that far in his quest for Elisabeth Saunders' heart yet. "I… I don't know."

"Like, do you want her to be your girlfriend? Or whatever it is that little kids do when they like each other?"

Sam thought long and hard, which was how he usually thought. "I guess I just want her to like me," he said at last.

"Okay, well, first you're going to have to tell her you like her," Dean advised. "Otherwise this whole campaign is going nowhere."

Sam panicked. "I can't tell her that! What if she doesn't like me back? It would be super embarassing!"

"Aw, Sam, don't shoot down your chances before you've even started. Let's just start with talking to her, alright?" Dean smirked at him. "Have you even said two words to her since we moved here?"

"Of course," Sam said defensively. When Dean raised an eyebrow, he admitted, "Well… one. I said thanks once when she held the door for me."

"Now there, Sammy boy, is your first mistake. You gotta hold the door for the lady, not let her hold it for you." Dean shook his head in clear disappointment. "Guess the whole gentleman manners thing got lost somewhere in between rock salt guns and summoning rituals, huh?"

"So what do I do?" Sam begged desperately.

Dean ruffled his little brother's hair affectionately. "Let's start by saying hello."