A/N: I absolutely love Nate/Vanessa. That ship could be so awesome. Here's my little backstory to their soon-to-be romance.

Disclaimer: I own nothing but Clara's mole. The song used is "If I Fell" by the Beatles.

The reviews have been great, I think I'm gonna write one from V's POV after the date, as a companion-fic.

If I fell in love with you

Would you promise to be true

And help me understand

He remembers first seeing her, at Blair's masquerade ball. Sure, she was masked, but he saw her a few days after. Nothing special, he had thought, at least compared to Blair or Serena. He noticed that she almost always had her video camera with her, recording the stupid jokes she and Dan Humphrey shared. Nothing extraordinary at all, Miss Veronica Adams or Veruca-something.

Cos I've been in love before
And I found that love was more
Than just holding hands

Vanessa. Her name was Vanessa. He had heard from Blair that Serena was worried about Dan and Vanessa maybe liking each other more than friends. Blair called her a "little stalker tramp who doesn't know the difference between Stella McCartney and Paul McCartney". He had laughed at that, knowing full well that Vanessa would often sit in the park alone blasting the Beatles while Dan and Serena would make googly eyes at each other. One day, while walking with Chuck, he caught a glimpse of her. Somehow, just seeing her felt slightly eerie, and Chuck soon brought the conversation soon to Blair once more, dragging Vanessa out.

If I give my heart to you
I must be sure
From the very start
That you would love me more than her

He was broken.
What's worse than being broken, is being broken by the people you loved the most and having to live with that. Humphrey's little sister had spread the news blissfully of Blair and Chuck's secret relationship. It was terrible at first, he had to rely on overly polite acquaintances for company. He didn't eat. Didn't sleep. Walks to his father's rehab clinic became more and more frequent. One day, he cursed Dan and Serena in spite for being so happy and perfect. Why didn't he deserve that? Only the next day did he catch Vanessa walking glumly behind the two. Yet yards away, she looked like every happy word between the couple were killing her. Oh well, he figured having your best friend cheat on you with your girlfriend was worse than your best friend falling in love with someone else.

If I trust in you oh please
Don't run and hide
If I love you too oh please

His walks to the clinic were more and more frequent. He left once as soon as the school bell rang and strolled casually there. It looked like rain once he left his father to play card with other Navy men, but he didn't think anything of it.

It started to pour, and he was soon soaked to the bone. His only refuge was a little rundown cafe. He sat uncomfortably at a back table, waiting patiently for the scarce waitresses to come serve him. A middle aged woman came, with a mole the size of Manhattan. It was hypnotizing, he couldn't even answer when she kindly asked him "what can I get ya, shug?". She left without answer, obviously assuming him to be deaf or something of that sort.

Don't hurt my pride like her
Cos I couldn't stand the pain
And I would be sad if our new love was in vain

"So, you gonna buy something or stare at Clara's mole? Even with that last one, you gotta buy something." She said, grinning a little crooked smile. Vanessa. Vanessa worked here, he was mildly shocked at her appearance, but it was oddly comforting.

"Uh...yes. Cappuccino?" He asked, looking down at the scuffed floors. How come he had never talked to her? Their social class circles overlapped sometimes these days.

"Fresh out. Josh went to go buy some coffee beans."

"Water?"

"Water it is." She sauntered off toward the kitchen, straightening out the purple frayed apron as she went. If this was another restaurant, chances are he would have left by now and gotten half of the UES to avoid this place like the plague.

But he didn't.

So I hope you see that I
Would love to love you
And that she will cry
When she learns we are two
Cos I couldn't stand the pain
And I would be sad if our new love was in vain

Three minutes later, Vanessa reappeared with two cups of water on her serving plate and a laptop bag on her arm.

"Here's your water. And, this table gets the best reception, and I got some stuff to do. Mind if I sit here?"

"No, uh, mi table es su table." Damn, why did he have to take Spanish? Stupid, stupid, she must think he's completely inept at being a normal human.

She snorted a little, and pulled out her red laptop and reading glasses and types at a seemingly unhuman speed. He stared a bit at her, completely unaware. She caught him the first time and smirked. The second she just shook her head. The third, she spoke again.

"I'm Vanessa, by the way."

"Yeah, Dan's friend?" He silently thanked the heavens for giving him a reasonable answer this time.

"Yeah," The two were silent for a moment, until she broke the barrier. "Got a name, St. Jude's boy?" She nodded at his school uniform as she said that, still managing to type at the sane time.

He laughed a little at that, he didn't realize that it was highly uncommon to see someone from an UES private school, soaked from the rain, and walking around Brooklyn to a rehab clinic. Even he had to admit the turn of events were slightly ironic.

"Yeah. I'm Nate."

So I hope you see that I
Would love to love you
And that she will cry
When she learns we are two
If I fell in love with you