Disclaimer: Glee is not mine. Don't sue. Please.
Author's note: Oh, God. It wasn't supposed to be this long but I guess I couldn't stop. It probably sucks but I wanted to try my hand in writing Rachel/Jesse.
Summary: His dreams and his ambitions makes him do stupid things sometimes, agreeing to go along with Shelby's plan is probably one of the stupidest.
Contrary to popular belief, Jesse hasn't had a lot of girlfriends. His entire life is singing and performing and giving impromptu concerts to those less fortunate than him (which let's be honest here, is mostly everyone), all the time he has left is for sleep and nothing else.
He vaguely remembers his first girlfriend. Her name was Allison and she was pretty and blonde and giggled and blushed whenever he sang to her. He thinks that's what he liked the most about her. She breaks up with him because she thinks that he cares more about his singing than her and he agrees to it because he knows she's right on.
Karen was his first love. He remembers first meeting her during a Vocal Adrenaline audition, he doesn't think much of her at first, her hair is in a sloppy ponytail and her look certainly doesn't scream "STAR!" but once she opened her mouth and sang, he's pretty sure he can feel his heart beating out of his chest. They win Nationals together and there's a moment after Vocal Adrenaline is announced as the National Champions and she's in his arms that he thinks they could last forever. Forever turns out to be only a year. After awhile the spark just isn't there anymore and once their coach notices this particular dilemma their duets are gone and Jesse is back to singing with a different girl for every number. He gives up on love after that.
Jesse has all the confidence in the world in Vocal Adrenaline. He knows they have the moves to make it far and win their fourth consecutive National Championships and of course having him, as their lead certainly doesn't hurt. So he's not exactly shaking in his boots when he hears about Nude Erections (or is it New Directions? Whatever. Jesse could care less) from William McKinley High making waves in the glee world. He's sent by Shelby to go to Regionals and see what they're up against (he argues that his time is more well spent practicing Highway to Hell but she's the coach and if he wants to be honest she kind of scares the crap out of him) and by the time the deaf kids start singing (really?) he's practically ready to gouge his eyes out but then 'Don't Rain on My Parade' starts up and Rachel Berry opens her mouth and the first thing that comes to his mind is whoa. Jesse St. James is hardly impressed by anyone, he's got impeccable hearing and he's capable of hearing bum notes that others who haven't had as much training as him can't, but if Jesse was asked to describe her performance in one word he'd most likely say flawless. The rest of the performance is pretty solid as well and he realizes watching them that what New Directions (he admits he kind of liked Nude Erections better) lacks in coordinated dance moves they make up for in heart.
The thing with Rachel begins with him being genuinely interested in her, he can't get her out of his head and what's eerie is that Shelby looks a hell of a lot like her which is totally not helping his current situation, so he decides to go to his favourite music store to calm down a bit and lo and behold, there in front of him is Rachel Berry studying some Lionel Richie. Jesse introduces himself as a fellow Lionel Richie lover, criticizes Don't Rain on My Parade (not only is he an excellent singer he's also a capable actor), compliments her on her talent, tells her about his full ride to the UCLA and his impromptu concerts and then they sing and it's perfect. Like, seriously bone tingling perfect. Its like they were born to sing together or something (Oh, god. He really needs to stop talking in clichés). They schedule a date on Friday and he can't help but grin back when he sees a big smile dawning on Rachel's face.
Their first date is spent singing "Hello" to the homeless and sitting on a park bench arguing over which Sondheim musical is the best (this occurred for hours and eventually they just gave up and admitted that there's just way too many great ones to really decide). The date ends with him driving her back to her house, walking her to her doorstep, her looking up at him with those big brown eyes and him kissing the hell out of her. He tries to think of one but he fails at finding a day that was more perfect than the one he had with Rachel.
It all goes downhill when Shelby finds out about his fraternizing with the enemy and of course, her being Shelby (aka evil in the form of a glee coach) decides to use it to her advantage. She insists that he continues dating Rachel (no arguments on that one) and insists that any info that Rachel might mention about New Directions should immediately be sent to her. She plays the "If you really want to be a star then you'd do whatever it takes" card on him and he hates himself a little for saying yes. If you ask anyone who thinks they know Jesse, they'd tell you that he's one of the most confident person they know but Jesse has doubts and he has fears just like anyone else and the idea of staying in Lima for the rest of his life is enough to make him wake up in cold sweat. His dreams and his ambitions makes him do stupid things sometimes, agreeing to go along with Shelby's plan is probably one of the stupidest.
His heart breaks a little when during the day they were trying to decide a new song to sing for one of their impromptu concerts Rachel takes his hand and tells him "My friends may have doubted your intentions Jesse but I know that you truly care for me." He tries to look at anything but her eyes but he's too late and the next thing he knows everything he's been hiding comes spilling out and the last thing he remembers is Rachel slamming her front door on him.
Everything just turns worse after that. Shelby finds out that he spilled her plans so he's no longer in Vocal Adrenaline (he's not too torn up about it though since she eventually got what she deserved and got fired after the school found out that a majority of the girls in Vocal Adrenaline were starving themselves to stay thin due to Shelby telling them to), Rachel won't take any of his calls and his impromptu concerts have been banned by the police since he's supposedly "interrupting the peace". There's nothing wrong with wanting to serenade a couple of people that are down on their luck at two o'clock in the morning okay?
He decides to gather some new music to pour his heart into (there's only so many times you can sing "All By Myself" without getting sick of it) so he goes to the only decent music store in Lima, sadly it happens to be the same store where he and Rachel were first introduced but he tries to forget about that particularly memory and decides to roam around the ballad section. He practically drops the cd he's holding when he sees Rachel entering the store looking like she's deep in thought. He contemplates leaving her alone for a minute but he pep talks himself out of it ("C'mon Jesse get it together. You're Jesse mothereffing' St. James. Where has your mojo gone?") and decides to go his usual route (which is being direct and to the point), he walks up to the piano and sings the only song he knows that has the word sorry in the title.
What do I do to make you want me
What have I got to do to be heard
What do I say when it's all over
And sorry seems to be the hardest word
Rachel head immediately snaps (he's sort of reminded of that woman in the exorcist except Rachel is much prettier of course) towards him and he's not exactly sure whether she's pissed or happy but seeing that she hasn't walked over to him yet and slapped him, he'd like to think it was the latter. He finishes the song and the crowd is clapping and Rachel is walking up to him and he thinks to himself, "If this somehow ends with her and I kissing as the crowd is applauding, I'm not even going to complain about the utter cheesiness of it all."
Instead what he gets is this:
"Your particular version of that classic Elton John song was thoroughly flawed. Clearly you're out of practice but…you are talented."