Disclaimer: I do not own Glee, Jesse St. James or Rachel Berry.

The first time Jesse St. James falls for a girl, it's almost too easy to get her to fall for him as well. It's Valentine's Day in fifth grade. Prior to this date, Jesse hadn't given girls much thought. There's his sister, but she hardly counts, and his mother, who is a mother and therefore really doesn't count. There are various cousins and grandmothers and aunts but he hardly ever sees them so he never dwells on their existence much. The only girl that counted that he spared any thought towards was this girl in chorus with him. She stood behind his right shoulder and wouldn't know how to hit a right note if a gun was trained on her. It was distracting, and left Jesse rather unimpressed with the concept of the female gender. However, now it was fifth grade and Valentine's Day and he had to get everyone a Valentine's Day card.

The sending of Valentine's Day cards was a lost art to the Discovery Montessori School in Akron. How was he supposed to feel special (and vice versa, he supposed) when his classmates were forced to send cards? What sort of message was that? To make up for such a thing, Jesse made his own Valentine's Day cards rather than buying some generic cartoon ones and slipping them into people's card boxes. His mother had suggested the idea, said it was only natural for him to as he was so artistically gifted. However, this had lead to fifth grade and being banned from participating in Valentine's Day.

With homemade Valentine's Day cards had come homemade messages. Jesse was nothing if not honest, as his father had told him that people were better for honesty than harboring under delusions of dishonesty, and so he had written rather heartfelt messages in his cards.

It seemed to be that his classmates preferred to harbor delusions of dishonesty than to know what Jesse St. James thought about them.

This girl had not been there for that particular fourth grade fiasco. Her name was Carly Lynne and she transferred on Valentine's Day. She looked like a Carly Lynne, too, all strawberry curls and a faint southern accent. When she was introduced the teacher had said she had just moved from Missouri…or Mississippi…Michigan? It had started with an M, at least. Jesse rarely listened to anything that did not hold previous interest to him.

Since she just started on Valentine's Day, she had no Valentine's waiting for her. She sat in the back corner, her eyes trained away from the festivities. It was weird to Jesse; he didn't understand why people would sit in the back or sulk in corners. He preferred sitting up front, where he could be seen by the most amount of people. But she had looked pretty, and like she could sing (he could tell these sort of things, it was one of his gifts), so he had made an exception and sat next to her.

After the introductions, they had fallen into silence. Finally, she sighed. Jesse always enjoyed dramatic gestures, in any form.

"I don't have any Valentine's."

She seemed upset about it, and again he didn't understand why. They didn't mean anything, everyone had to get one for everyone. (Except Jesse. He had to bring in cookies.)

"Me either."

Jesse had no idea whether or not this was the truth, but he assumed that his classmates were encouraged to skip him this round as he could not provide Valentine's for them.

Her eyes had widened at that. She was smart, for a new girl, the card fiasco had only served to make him more popular. At least, amongst his friends. He didn't really care about the others. (And had said so in his cards.)

"Really?"

Jesse had bitten his lip, all bashfulness and none of the indifference he truly felt, "Truly."

Jesse St. James was going to be a star one day, and practice made perfect. (Everything was a potential acting exercise.)

"That's terrible," she declared, standing up. "I'm going to make you a Valentine's card."

"You don't have to." Jesse put the right amount of hesitancy in his voice. In truth, he was rather falling in love with her. After all, this would be a Valentine's Day card just for him, and she would make none for the rest of the class. "But that's really cool of you."

She had beamed. If he was in the sixth grade version of falling in love, then she was already head over heels in love with him. "You seem nice, you should get a card."

He didn't make her a card during class, as that would have appeared as though he was just making her one because she was making him one. But during lunch he disappeared into the art room and made her five. One for each letter of her first name, and slipped it into her bag before she came back from recess.

After school, he had been standing outside waiting for his father to pick him up when she had run up to him. Her face was redder than her hair and she held the cards in her hands. He thought she was going to thank him, but instead she said nothing. Just made some sort of squealing sound in her throat, before throwing her arms around him and giving him his first kiss.

The knowledge that he could get a girl to like him like that after knowing him less than eight hours was probably the best and worst lesson Jesse St. James could ever learn.

The first time Jesse St. James convinced a girl to sleep with him he had been a freshman in high school. His fifth grade romance with Carly Lynne had lasted a solid two months before their relationship had met a tragic end. After she had kissed him for the first time, she had made a few more unintelligible sounds and run away. When he had gotten home, he had asked his older brother about it. His brother's response was to high five him, and so Jesse took that to mean he had done something awesome. And should continue to do awesome things.

The next day and days after that, Jesse would seek Carly out on the playground and the two would disappear to a hidden spot and kiss. It was rather innocent. The two didn't know anything about kissing, or sex for that matter, and would just give each other a series of pecks on the lips. However, one fateful day in April, the gym teacher came across them and landed them both in the principal's office with their parents. After that, she was too scared to kiss Jesse and their romance fizzled away.

This did not deter Jesse from finding other girls to kiss and date. It wasn't that he was a serial kisser. That would be gross. Too many germs could pass through those lips and he would end up sick with a cold. A cold was one of the worst things Jesse could contract.

In his first year of high school he joined Vocal Adrenaline. They were a nationally ranked team, coming fifth place the previous year. Fifth place, his coach had said on his first day, was four places below where they should be and therefore did not count. This was a mentality he could get behind.

Jesse did not start out as the lead. He had to be trained, or in some cases retrained, to make sure he was using his voice correctly. Too many singers were singing incorrectly and damaging their voices, Shelby Corcoran had explained. That sounded tragic so Jesse took everything Coach Corcoran said very seriously. He was paired up frequently with a sophomore girl who had been promoted from being an alternate after one of the other girls had broken her wrist when attempting one Vocal Adrenaline's more challenging stunts. Her name is Maya Tedesco.

She's insecure and he continuously outperforms her. She has potential though, even if she seems hesitant to tap into that. It brings down his own performing level and Shelby seemed disappointed in him. One evening, after practice he can't take it anymore. Jesse St. James was never meant to be a background player. So he offers to do extra rehearsal with her. He tries to be subtle, but she knows she sucks. It's a point in her favor, not everyone has the ability to see when they are terrible. It was always painful to watch and even more painful to listen.

Maya is not that great. The fact that she is an alternate is extremely obvious but she's willing to learn and follows his instruction. After the first sessions or so he notices that she's pretty. It's also after she becomes adequately good on a song that she was previously mediocre on. Not everything is tied into a girl's level of talent, but it certainly helps.

By the end of the week, she's improved enough that it is no longer distracting him when he has to sing with her. He celebrates by kissing her, and she lets him kiss her back. They've been doing the lessons at his house, as he has his own music room. It used to be his brother's room, but after he moved out they converted it into a soundproof room for Jesse to be able to sing whenever he desired to. Now when his brother comes home he sleeps on a pull out couch in their father's study. But they're at his house and it's convenient to continue the kissing and move it along down the hall to his bedroom. She doesn't attempt to give even one protest.

The next time Vocal Adrenaline meets it's their turn to perform, and he can see they've caught Coach Corcoran off guard. She had smiled widely and clapped, before addressing Jesse and asked if this was his doing. It was, and he takes all the credit for it that he deserves. Next thing he knows, he is made lead and puts Vocal Adrenaline into that first place spot at Nationals.

He forgets to talk to Maya again.

The first time a girl ever said no to Jesse St. James he was 18 years old, and the girl was Rachel Berry. (He wasn't sure why she said no. She had invited him to her house, said her parents weren't home, and then brought him up to her room. These events left him in a state of confusion for several days.)

The first time Jesse St. James fell in love was with Rachel Berry. (This, too, happened in her bedroom. It was surprisingly, but he knew it was really love because it crept up on him during a moment where she wasn't performing. He frequently fell in love with people's talent so it was not an emotion he all together trusted.)

The first person Jesse ever apologizes is to Rachel Berry. (The first person he ever apologizes to and means it is also Rachel Berry. The lesson learned from both these occurrences was that apologies never got you anywhere.)

The first heart Jesse ever intentionally breaks is Rachel Berry. (He does it because she begs him to. And because while he knows he's a phenomenal actor the one role he has never really been good at is that of being Jesse St. James and he tends to avoid anything he could potentially fail at.)

The first time Jesse attempts to make amends is with Rachel Berry. (He gives her a song, well a duet, an apology and an offer as amazing prom date in less than an hour. He thinks it might surpass his Carly Lynne achievement. He's wrong, but he frequently seems to be about Rachel. The one thing he never counts on with her is high school because she's so obviously above all of that he never considers that it matters.)

The first person to ever break his heart is Rachel Berry. (The less said about it, the better. It makes even less sense to him than when she said no to him, and is completely dependent on the high school factor he always underestimates.)

Jesse St. James is going to be a star. His achievements outweigh his failures. (One day, potentially. He wonders if it ever occurred to Shelby that the deal she made with him to ensure his fame would also be the one that could hold him back.)