Summary: AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

Disclaimer: I don't own Supernatural or its characters. I don't own anything concerning When Harry Met Sally, including some of the lines in this story.

A/N: Okay, I couldn't resist doing the Dean/Cas version of my favourite movie ever! Yes, Dean is bi in this so there are female and male partners, whereas with Castiel it's just male partners. I hope that you like this version, which I've dubbed When Harry Met Sally: The Gay, Supernatural Version.

Happy reading!

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When Dean Met Cas

Chapter One

1998

Twenty-six year old Dean Winchester holds twenty-one year old Lisa Braeden in his embrace, the two of them kissing tenderly as they say their long goodbye. Dean, the handsome dark blonde-light brunette with stunning green eyes has just completed law school and is about to head to New York, therefore leaving Lisa behind. Lisa is his dark brunette girlfriend who he's been with for a while now, and who he really does love and respect. They're at the University of Chicago, Lisa's good friend Castiel, who is also going to New York, is going to drive Dean there. Upon breaking their kiss, the two smile at each other, Lisa looking dreamily into Dean's eyes.

"I love you." She says softly, earning a smile from her boyfriend.

"I love you too." Dean replies, pressing a deep kiss to her lips and holding her close to him, not noticing Castiel pull up in his dark blue Ford Granada.

Castiel, the twenty-one year old with the unbelievably gorgeous blue eyes and near-black hair, sits patiently and waits for the two to finish kissing. He watches them, beginning to feel uncomfortable as Lisa's backside gets fondled by the insanely hot guy she's kissing. Eventually he clears his throat, breaking them out of their kiss. He's heard about the fact that Dean's bisexual, so doesn't worry about any prejudice about him being gay.

"Oh, hey there, Cas!" Lisa says sweetly, Dean looking around to find a guy sitting in the driver's seat.

Cas is a guy?

"Cas, this is Dean Winchester," Lisa begins, "Dean, this is Castiel Novak."

"Nice to meet you." Dean says with a soft smile, watching Castiel smile up at him.

"You want to drive the first shift?" He asks, Dean shaking his head softly.

"No, you're already there, you can start." He replies, Castiel letting him know that the back's open for him to put his things in.

Dean packs his bags, and while he promises Lisa to call him and they start to kiss again. This is disgusting. He doesn't want to sit and bear witness to this, he wants to start the drive to New York. He beeps the horn, breaking the two apart while smiling sweetly at them. Ah, he loves Lisa very much, but watching Dean and her eat each other's faces off? No, thank you!

"Sorry!"

As Dean and Lisa say their final goodbyes, Dean climbs into the car beside Castiel and the two head away from the university and set off to New York. The drive is quiet to begin with, so Castiel decides to explain how he's planned the journey.

"Okay, I've figured all this out," He began, "We can do six shifts of three hours each or I've broken it down by mileage..."

He's cut off when Dean's gorgeous ass comes right into his view as the older man leans into the back to get something from his bag. God, it is a nice ass. Castiel has to keep his eye on the road, but it's so difficult when that beautiful backside is in his view.

"Th-there's a map on the visor which I've marked to show the locations where we can change shifts." He says, getting a shock when Dean sits back with a handful of grapes and shoves them in Castiel's face.

"You want a grape?"

Castiel turns back to focus on the road and shakes his head lightly.

"I don't like to eat between meals."

Dean spits out the grape seeds and Castiel sighs, reserving his anger as Dean turns back to him with a blank face.

"I'll roll down the window." He says, "So, why don't you tell me the story of your life?"

Another set of seeds are spat out of the window and Castiel shudders at the utter foulness of it, continuing to drive and finding a way to tell Dean that nothing much has happened in his life yet.

"The story of my life?" He asks, Dean nodding and munching on another grape.

"We've got eighteen hours to kill before we get to New York, so..." He says, spitting out more seeds.

"The story of my life won't even get out of this city, Dean." Castiel replies, "I mean, nothing's happened to me yet...Apart from finding out I was gay at the age of fifteen. That's why I'm going to New York."

"So something will happen to you?" Dean asks, Castiel nodding softly, "Like what?"

"Well, for a start I'm going to journalism school to become a reporter." He replies, waiting for Dean's answer.

He knows he won't like it because so far, Dean seems to be a bit of an ass. How right he is.

"So you can write about things that happen to other people?"

Castiel waited for a moment before speaking, since Dean's made him feel kinda bad about it.

"That's one way to look at it." He says quietly, barely able to bear Dean's next unbelievably dampening words to him.

"Suppose nothing happens to you." The older man says, "Suppose you live your whole life, nothing happens to you, you never meet anyone, you never become anything and you die one of those New York deaths that no-one knows about until two weeks later when the smell drifts into the hallway."

Castiel looks across at Dean who continues to eat his grapes, unaware that the young man next to him is actually terrified of spending the next eighteen hours in complete torture with this man who just astounds him with the things he comes out with.

When they reach the highway, the two have spoken some more and know each other a little more, so Castiel turns onto the topic of Lisa.

"Lisa said you had a dark side."

"Yeah," Dean says with a lopsided grin, "That's what drew her to me."

"Your dark side?" Castiel asks, earning a nod from Dean.

"Yeah, don't you have a dark side?" He asks, "No, you're probably one of those cheerful people who dots their 'i's with little hearts."

Castiel feels like he needs to defend himself now, because Dean is just blatantly ripping him to shreds and it hurts a little bit.

"I have just as much of a dark side as the next person."

"You do?" Dean asks, "Y'know when I get a new book, I read the last page first. That way, if I die before I get to the end, I know how it turns out. That, my friend, is a dark side."

"That doesn't make you deep or anything," Castiel begins, realising that he is in fact, a happy person, "Alright, basically I'm a happy person, and I don't see where the problem is with that."

"Of course you don't, you're too busy being happy." Dean says, "Do you ever think about death?"

Castiel pauses for a moment. He does think about death, just not as often as Dean probably does. It seems that Dean is one of those people who seems to have one up on every one else. Your typical ass. Perfect!

"Yes."

"Sure you do. A fleeting thought that drifts in and out of the transom of your mind." Dean says, "I spend hours. I spend days..."

"And this makes you think you're a better person?" Castiel snaps, finally pissed off with Dean and his attitude.

"Look, when Death finally comes for me, I'm gonna be prepared and you're not." Dean tells his him, calm to a point where Castiel could rip the steering wheel of his car out and beat him to death with it, "That's all I'm saying."

"Yeah?" Castiel asks, "And you're gonna ruin you're whole life waiting for it."

Dean's silence makes Castiel believe one thing. He's finally gotten to him.

That on its own brings a small smile to his lips.

-TBC-

Hope you enjoyed!

Thanks for reading so far!

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