Written for the 'CuteDeeen-a-thon' fest! Basically, I just wanted to make things better for the poor boy.

It Starts As the Sweetest of Love Stories

It starts as the sweetest of love stories. Home town boy—okay, actually transplanted Chicagoan boy—falls in love with lovely, sweetly innocent, scary smart Gilmore girl. Countless (or…at least five) obstacles rear up to block the path of true love. Gilmore girl is so smart that she goes away to super snotty, uber hard, Ivy League prep school—otherwise known as Chilton Academy—while boy languishes in public education. Fast talking, gimlet eyed, gorgeous mother—with way too much influence over said innocent young girl—is not sure she approves of Chicagoan boy. Blonde, preppy asshole named Tristan insists that this love story is actually about him. Grouchy diner owners and nosy, interfering townsfolk abound. Oh, and did we mention there are grandparents? Scary grandparents.

But obstacles are placed in their path to be overcome and they are. In the end, determined, freakishly tall, cute boy and luminous, slightly confused girl confess their eternal love and all is well with the world. It's their happy ending.

Or…not.

Because it turns out that hometown girl doesn't exactly know her own mind. Maybe she's in love with Chicago transplant boy—look, Dean, his name's Dean okay? But maybe home town g…Rory's version of love isn't quite the same as Dean's. Maybe she's not as in love with Dean as she should be. As he is with her. Because Rory's everything to Dean. The sun and the moon and the reason Shakespeare wrote his freaking sonnets. I mean, he doesn't say it because he's a guy but she's beauty and wit and depth and she sinks into his skin and his bones and his soul until it's so big and so real and so everything. It's his happy ending. Until it's not.

Because it turns out Rory doesn't think of him that way. Dean's not in Rory's skin or soul or freaking whatever. Not if she can choose a punk like Jess—oh you haven't heard about Jess? Trust me…you don't want to. But Dean has to figure that if Rory can be tempted away so easily by a stumpy little fake rebel punk like Jess then, as much as it feels like acid eating away at his body, as much as he wants to scream in his ex-girlfriend's face and destroy things and just hurt her, Dean has to face the fact she never really loved him the way he loved her. Rory never fucking loved him at all.

But Dean's a good guy. He doesn't go postal. He doesn't snap Rory's scrawny neck. He doesn't chop Jess into pieces and use him for fishing bait (although he does fantasize about it a God damn lot). He does what any decent at heart, freakishly tall all American boy does. He fucks up his own life instead.

He starts dating Lindsay, which…nice girl but dumb as a post. In fact, she's the antithesis of Rory. Dean knows that. He's got a brain. He understands psychology. And it's soothing for awhile to be with someone who looks at him like he's the quarterback of the football team and the smartest guy in the room. Of course anyone would look smart compared to Lindsay. Which is why he's pretty much bored after the third—okay fine, first—date. But her big, doe eyes and girlish giggles are soothing for his ego and she's good in bed and…hell, she really is a nice person. And Rory gets a snitty look on her face whenever she sees them together and in his heart of hearts Dean knows that's the biggest reason of all.

But then it kind of snowballs. After he gets his heart chainsawed by Rory, Dean's too busy bleeding out to really give a shit about grades and college and he's always liked working with his hands anyhow. And Lindsay really likes girly, glitterly shit, the kind you have to buy, so he starts working more hours and cutting back on his studying and pretty soon he's working so much that it's hard to really focus on college and then Lindsay's hinting at rings and there's a part somewhere 'not that deep' inside of him shaking in panic and shrieking and pounding against a locked door that gets thicker every day, howling out that this is not supposed to be his life.

Dean ignores that part of himself and fucking embraces the way things are because it feels like choosing to be an adult; walking away from stupid, fucked up, childish dreams of true love. And because if his life is off track he can blame Rory and there's a certain bitter satisfaction in that. Rory Gilmore is to blame for every screwed up thing his life has become.

And then Dean actually ends up married, Jesus fucking Christ, and the day is a sucking miserable black hole with a big ball of sheer unhappiness weighing him down and that voice is back screaming, raging into the void, but Dean's standing in front of a minister and the guests are here and there's no way back, no way out, so he opens his mouth and lies and gets married.

Only it doesn't fix anything. It doesn't magically get Rory out of his soul or his sinew or anywhere she's permanently settled like an ache now. Like arthritis and he's only fucking twenty years old and he feels old, ancient, tired and worn and angry; so angry. And pretty soon Lindsay doesn't look at him like he's Superman anymore. She looks at him with sad eyes, angry eyes, snitty eyes. And he can't really blame her but he does anyway. And he knows after every fight that what he's really blaming her for is not being Rory.

And then he ruins his life again. Because Rory comes back, trailing him around with wanting eyes and need and she's just as shining and beautiful and smart and the antithesis of everything his stupid life's become and he just wants so bad that he ignores the gnawing at his gut that says this is a mistake. Because it's not a mistake. This is right. This is meant to be. It was always supposed to be him and Rory. He doesn't want to hurt Lindsay but it's nothing, she's nothing to what he feels for this girl who had him at fifteen and never, ever let go.

And then reality hits with the subtlety of a sledge hammer and the pain is maybe worse than the first time because he knew, he knew better and he went in with open eyes because he wanted it so much, so bad, more than anything and now she's gone. Just fucking left him behind. Again. Without a word, without a note, she's fled the God damn continent. And the sad thing, the pathetic thing is that at first he's worried for her. Did he mess it up somehow? Is she okay? It was her first time; did he hurt her; did she have some sort of post-sex freak out? And then he finally gets his note; from Rory's mother. And that's just somehow the perfect kick in the balls topper to the fact that he's been fucked by the Gilmore's one more time.

Then Lindsay finds the note. And yeah, maybe some part of him—that part that's been pounding its fists and howling against its fate—wanted her to find the note. He left it in his jacket. The jacket his wife puts away for him. Yeah, maybe part of him wanted his wife to know. But then she does know and it's awful. The hurt in Lindsay's face, in the crushed lines of her body, the pain he's caused this girl who never did a thing to him but try and make him happy. The look on his parents' faces, Jesus. He's never felt this small, this wrong, this much of a fuck up. And the look on his little sister's face is maybe the worst thing of all because he's always been Dean—best brother in the world—to her. To his sister he knows everything, can do anything, he's always been her larger than life hero. But after Lindsay, the reflection Dean sees in her young eyes is nothing but human; flawed, sad and human.

Dean doesn't know how to be anything but angry at this point. He moves back in with his parents, works hard, studies hard, keeps his sentences short and terse; avoids looking anyone in the eyes and simmers right at the edge of a boil for months. He drinks a lot of beer, goes out on weekends to neighboring towns, gets laid by girls who look nothing like Rory God damn Gilmore and wishes savagely that he'd never met her, never fallen so hard to end so wrecked. He thinks about himself at fifteen, happy and sure of himself; quietly confident and capable of almost anything. He wonders how he lost that; how he ended up this uncomfortable and miserable in his own skin; but then again, he knows exactly how he ended up like this.

When Dean hears through the Stars Hollow grapevine that Luke Danes and Lorelai Gilmore are together he just shakes his head in disbelief. The dude should know better. God, it's like knowing the train's going to wreck before it even finishes pulling out of the station. Dean likes Luke; he respects the guy. Yeah, maybe they've had their differences because Luke's not exactly Mr. Sparkling Personality but he doesn't want to see the guy crushed like a bug under the sparkly, stiletto heel of a Gilmore either and that's exactly what's gonna happen.

He finally works up to telling Luke that, the rage and the bitterness pouring out of him and even as he's venting he can see that Luke's not listening, won't listen, because Luke's gone; he's under the Gilmore spell and Dean knows exactly how that feels. But something about the conversation; something about spewing out his venom on Luke makes the hard knot of tension loosen up inside of him. For the first time in months, he feels calm inside of himself; for the first time in months he feels the weight that's been pressing against his chest, keeping him from taking a full breath, ease up.

That weekend, instead of going out with the construction guys and getting drunk and getting laid he hauls some of his dad's old camping gear out of the garage and goes fishing. It's the huge cliché of heading back to nature but it works. Dean lies down to a night in the untouched Connecticut wilderness staring up at the blanket of countless bright stars and lets silence, the perfect silence and the clean, sharp air settle him; and he realizes with clarity as sharp as the night that he has to go. If he stays in Stars Hollow he'll always be just a footnote in the life of Rory Gilmore. Her first boyfriend. A marriage she broke up. A boy she discarded on her rise to whatever glory she'll eventually find—and he has no doubt she'll find it. He'll always be defined by her and he doesn't want to be anymore. He'll never be Dean again if he stays.

It's not easy. Dean's folks aren't rich and they can't help much and his grades haven't exactly been stellar the past few semesters but he knows how to work hard, how to focus and at least now he has a goal. It's getting away, getting past this, starting fresh. It's a relief to have something tangible and achievable to focus on. Dean works hard, saving money; he studies hard, hitting the books; and things slowly settle at home. His parents love him, this he knows. And, as angry and disappointed as they've been, overriding it all has been their worry for him. He thankfully sees it fade away into relief as they watch him settle down with his new found purpose and wen he tells them about transferring out of state they quietly support him and offer him what help they can.

It takes Dean another eight months before he has the money saved—though he'll be working like a dog until he graduates—and the grades to transfer to another school. It might be easier to go one or two states away, maybe Massachusetts or New York or even heading back to Chicago where he'll still have the support system of family. But he figures fresh start means getting as far the hell away from Connecticut as he can and so he ends up registered as a transfer to Hearst College in Sunny California, one of a dozen schools he applied to. They're willing to give him some financial aid and though he'll lose credits, almost a full semester, it's worth it.

Dean spends the first few weeks wondering what the hell he was thinking. California is just so…sunny. He kinda hates it. He wears shades all the time because the bright sun gives him a headache and he feels like he walks too fast but it's everyone else walking too slow like they don't have anyplace they need to be. The people are weird here too but, Jesus after spending his impressionable teen years dealing with cat funerals, cheerfully lecherous dance instructors and Kirk it's not like he doesn't know how to deal with weirdness on an epic scale.

He finds housing off campus, sharing it with three other guys and they're just so…young. They're his age, one's even older, but they're all brand new and cocky and they're like unscarred young lions, not yet bloodied up by life. They're impressed that he's been married and divorced; that he knows his way around cars and construction. They're impressed by the sheer massive size of him. Dean overhears them talking about the fact that he's a 'friggin' man's man.' It makes him chuckle.

Dean's never had trouble making friends and he makes them here as he slowly settles in, eventually coming to the conclusion that California is okay. It's still too fucking bright though. He slowly sheds his layers of clothes and ends up in t-shirts and jeans most of the time—wearing shorts to class just feels too weird. He learns to appreciate the feel of the sun, the reliable warmth against his skin. He even buys a pair of the flip flops that everyone in the state seems to own. One weekend, he lets his roommate Steve, a total California nut job complete with vegan diet and bleached blonde hair, talk him into trying surfing and Dean falls in love with it, the rhythm, the rush, the feeling of peace that settles into his soul when he finds himself riding the crest of a wave or just lying out there waiting, riding the gentle rhythm of the swells and listening to the lapping of the water. He buys a used surfboard and starts spending his very limited spare time out on the water, his hair slowly bleaching as his skin takes on a deep bronze.

Half way into his first semester Dean knows he's made the right choice, realizing the tightness in his chest has settled and unfurled like a plant that needed sun—yeah, the sun really isn't so bad here after all. One day as he's walking between classes it just sort of hits him; he's…happy? Wow, he realizes with surprise. He really is.

He's doing well in his classes and he likes his roommates—Cole and Gary and even nut job California vegan Steve. They've knitted themselves into friends, hanging out, playing pool, eyeing girls. Dean's leery about dating much and he keeps his hook ups casual. He doesn't have a lot of free time between work and school anyway. He's lucky he managed to score a job in a mechanic's shop that caters to a lot of the wealthy. The pay's good and a surprising number of women of all ages show up to get their cars tuned and stay to proposition him. Dean sheepishly apologizes to the owner, Jerry, after the third time it happens in two shifts but his boss thinks it's hysterical, not to mention good for business. The guys at the shop start making bets on when the next rich, bored socialite/school girl/matron is going to make the moves on him. Louie wins the first pot by 3 o'clock.

Dean falls back into the groove of studying and he likes it; likes his classes; likes the stimulation. He likes it so much he starts thinking about going for a teaching degree. He can see himself on the other side some day; in front of a classroom shaping impressionable young minds. The thought makes him want to smile. He's also thinking that maybe it's time to try for something a little more serious than a weekend hookup. There's this tiny, quippy blonde who sits three rows in front of him in his psychology class. There's something about her. And best of all she doesn't remind him of anyone except herself. He decides to ask her out for coffee sometime. She can only say no.

Seeing the e-mail catches him by surprise. He just sits there for a minute, trying to decide how he feels about hearing from the girl he had to move a country length across to put out of his mind. Finally he shrugs and opens it. It's friendly and hesitant, filled with cautious pleasantries and rambling chatter that manages to sound fast paced even in written form. As he reads through it twice Dean realizes with pleased surprise that Rory's message isn't filling him with anger, or hurt, or pained longing. Maybe there's a wistful sort of ache in his chest but it's...okay. He hesitates and then hits delete without responding. No sense pushing his luck.

As he walks home from the library that night he smiles, a broad, flashing grin that no one's around to see. Maybe he'll ask out the blonde tomorrow.

The End