He wasn't a big drinker, never had been. Alcohol tasted alright, but it had never been worth it for him. A glass of wine with dinner, perhaps. A beer or two while out on the town with friends. But he handled his liquor well, so Jesse St. James had never bothered getting smashed on a regular basis. Not that he had had time during his adult formative years. He'd been too busy with Vocal Adrenaline to even think about inducing a hangover of any kind. Shelby Corcoran was much to vicious to those who showed up with a hangover.

He'd done it once, of course. On a sponsored spring break trip to Cabo with the rest of his team. He'd had to drink almost twice as much as everyone else to feel the same way. And it wasn't worth it. He woke up alone, just as usual, and he woke up in pain. So Jesse swore of the heavy parties, and heavy drinking that seemed to come with his age.

That was, until he met Rachel Berry.

He'd been contracted to get to know her, of course, by her mother. But he hadn't expected to actually fall in love with her. She was his perfect match. She could keep up with him in every part of life that he deemed important. And she had fallen for another boy. An idiot of a boy. They could have had absolutely everything that they'd mutually every dreamed of, and Jesse had lost. It was insulting.

He didn't think much of it, he turned around and called it an acting exercise to her face, when she broke his heart with her little video. The idea of being triple cast in the first place actually hurt less than who he'd been cast against. Noah Puckerman, and Finn Hudson, the bane of his very existence. It was insulting, to be triple cast against two former boyfriends. He was hurt. He was angry. Enough to revert back to the original plan. Because it was obvious now that Rachel didn't see them the way that he did. They weren't an inevitability. He was just a rebound for that idiot boy. And so he moved back in with his parents, enrolled back into Carmel, and followed his team to her school to egg her. To prove his allegiance, they'd said.

The sight of her covered in eggs should have been a relief. He'd crushed his opponent, broken her to the point that there was no way that he could lose in competition. But it only upset him more. He set his jaw, and took a deep breath before he turned away to smile for his teammates. There was a short celebration. An inauguration back into the fold. But that wasn't enough for Jesse.

He found himself alone at home that night. Not unusual. His parents were too busy to bother being home on a friday night like this. Jesse wasn't really thinking when he found himself sitting at the kitchen table with scotch from his father's liquor cabinet. He still had stains of egg on his jeans, and he was on his 5th glass before he started to feel it. The complete and utter despair. His pride had gotten in the way. The look on her face when she'd run up to him. He'd never forget that. She'd looked so happy to see him, she'd thought that he was going to forgive her for the debacle that had been Run Joey Run. He could have had her back. The look in her eyes, the look that was burned into every part of his mind, had said it all. And he'd gone and ruined it. For what? For another national title? Jesse downed an eighth glass of scotch and fell forward onto the table, his arms serving as a cushion. He'd never cried that hard. Crying wasn't allowed in the St. James household. A sign of weakness, and weakness bred contempt from others.

It was almost a year before he saw her again. His body had been acting on it's own accord to find her. The auditorium.. Jesse heard her voice and couldn't help but join in. She was even more beautiful than he remembered. It took a few weeks of talking, but he'd managed to earn her forgiveness. More than forgiveness. Jesse had earned a date. And a prom date at that. Everything was going perfectly. It was a beautiful night, save for a massive annoying incident named Finn Hudson. But Jesse was on top. He had her again. He had another chance.

And without him to compete against, New Directions managed to beat out the Dalton Academy Warblers to go to Nationals in New York. He wasn't supposed to go, he was still in a bit of trouble with his parents for bailing out of college. But, as usual, they didn't care enough about their family life to stop him from galavanting off to the big apple to surprise her. His girlfriend? He'd like to think that's what she was. She'd never forgive him if he distracted her with talk of relationships or love before a show, so he would surprise he after the performance and take her out for a beautiful night. Dinner, a stroll.. to see the city that she would one day call her home.

He hadn't been sitting for more than 5 minutes when he saw it. Finn Hudson. Again. In that moment, Jesse was shattered. This time, he'd done nothing wrong, and he was still losing. Was it pathetic to pine after someone so obviously in love with someone else? Regardless of how completely ill-matched they were? He couldn't make her happy. He was too oblivious... Jesse had a few choice words to share with them after the performance. The kiss had lost it for them, and what was meant to have been a happy surprise for his.. for Rachel had turned into a harsh slap from reality.

That night, Jesse found his way to the hotel bar. It took almost ten glasses of scotch this time. He'd flown all this way, and for what? To be shown that he wasn't worth it, again. He ordered another, and the bartender refused. Jesse pushed the glass away, and started his way back up to his room. He passed out that night, alone. He'd gotten a suite, so that he could bring Rachel back and look out at the city that she would own in a few years, fall asleep curled up next to her. But now it was just sad. He didn't make it to the bed, instead curling up on the floor in the small living room, in between the couch and the coffee table.

Ruin could be the best word to describe what Jesse's life had turned into. What had been a bright and shining future two years ago had become the saddest existence in the world. He drilled his students relentlessly. Those who'd been there under the guidance of Shelby Corcoran would say that Jesse St. James was at least ten times worse. He ran his rehearsals harshly. He demanded perfection. If he couldn't succeed he'd be damned sure that Vocal Adrenaline would.

Jesse had learned to push thought of Rachel Berry far from his mind. His life was the show choir. At least until he got his results back from various schools across the country. Next year, he would pick his life back up again. Go back to college, succeed. He would be what he'd always set out to be. Which was why he needed this win. A new start to the new St. James legacy.

It wasn't until Kurt Hummel and Mercedes Jones showed up at one of his rehearsals that New Directions and their shining star popped back into the foreground of his mind. He'd always known who he'd be up against. They'd made it to Nationals last year, so they clearly knew how this year. If he was rude to them, it was only because of what they represented. And because it felt good. Just a little.

When he saw her in Chicago, he put on his show face immediately. She saw right through it. It was sweet that she still knew him so well. Maybe he could ask her for coffee sometime. They could get to know each other again, and he could have a third chance at his only equal in the world. That idea was crushed, however, by the gaudy little ring on her finger.

Engaged. Of course she was. If there was anyone who could bring a star down from the sky and cage it up it was Finn Hudson. He smiled, and congratulated them. Told Rachel that he was eager to see her performance, and even managed to get out a few civil words to Finn. All in all, a successful show.

There was some time before they were set to perform, and Jesse once again found himself in the bar. The conference center where the performances were being held had a particularly posh selection of drinks, but Jesse ordered a scotch. He managed to get down twelve glasses before he realized what time it was. He had to go.

Jesse straightened out his suit jacket and paid the bartender, with a heavy tip, and found his way to the concert hall. He wasn't falling over, which was a good sign. The only tip that he was even drunk was the stain of the scotch on his breath.

After the performance, he saw Carmen Tibideaux. If he'd not been so drunk he never would have gone up to her. But Rachel deserved it.. because who else could she possibly be there for? He waxed poetic about Rachel's talent, and gave the most heartfelt speech that he could manage. For once, he was completely honest to someone about the way he felt.

She was engaged now, there was no point in trying to win brownie points with her. She was going to get married, settled in Lima, have a whole nest of awkwardly sized children. But if she was happy, then Jesse would have to live with it.
He never really moved on. He made it to Broadway, without her, the way that he'd planned to do in the beginning. He pushed all thoughts of the young girl who'd turned his life upside down. It wasn't until he was thirty that he saw her again. She was with her family, Rachel, Finn, two beautiful young boys with dark hair. They were crossing the street in front of the bar where he'd set up camp for the evening.