Nate's First Try:

Disclaimer: I don't own Gossip Girl nor do I own the song below by Taylor Swift, which I based the story off. All I own are my crazy ideas.

You can see that I've been crying
And baby you know all the right things: to say
But do you honestly expect me to believe
We could ever be the same...
You say that the past is the past, you need one chance
It was a moment of weakness and you said yes...

-Should've Said No by Taylor Swift

'Flowers? Check. Nice smelling breath? Check. Fancy-shmancy ruby ring Chuck picked out for me to give as a token of apology. Triple check,' Nathaniel "Nate" Archibald thought this as he walked from his penthouse to his ex-girlfriend (for the moment), Blair Waldorf's, suite.

Yesterday had been an absolute nightmare. After living with the guilt of having sex with Serena at the Shepards' wedding, Nate had finally come clean. The results of his honesty, however, were disastrous. Blair cried, cursed at him loudly, and ordered him to leave. He was so scared of what Blair would do if he did not leave that he practically ran out the door.

Blair Waldorf was widely known for her rage, revenge plots, and overall bitchiness, after all.

Nate got into the elevator and pressed the button for the penthouse. The elevator whooshed up the stories and soon, Nate was there.

Wringing his hands nervously, he spotted Dorota cleaning a priceless vase meticulously. He thought it best to ask Dorota to get Blair for him instead of going up himself. He had already experienced the pain of one of her Manolo Blahnik shoes, thank you very much.

"Dorota?" he called out. His voice echoed. In some childish part of his mind, he thought 'Cool!'

"Yes, Mister Nate?" Dorota answered politely, stopping the cleaning of the already spotless vase.

"Um, can you ask Blair to come down? I need to talk to her," he responded.

"Of course," she nodded. Dorota briskly marched up the winding staircase and knocked on a door. Nate heard furtive whispers and the rustle of footsteps.

Blair walked down the spiral staircase, with her head held high and a cold, blank expression on her face. When she finally reached the bottom of the stairs, she turned her head and looked at Nate, her face growing stonier even more. She was still wearing the slip from the night before, but had added a long sweater that skimmed the tiled floor of the penthouse. Her pale feet were bare.

"Nate." she said stonily.

"Hey Blair. I came to talk to you," Nate gulped. He was extremely nervous. His parents had forced him to get Blair back. If he didn't, there would be hell to pay.

"I can see that. Now, spit it out so I can leave your disgusting presence. Just looking at you is making me want to run to the nearest restroom."

'Like you ever really had a problem throwing up in the bathroom!' Nate thought. Yes, he knew all about her bulimia problem, even though everyone thought he was blind to the fact. He just ignored it, as he ignored much of what Blair did. Nevertheless, he pushed the thought aside and got back to his mission.

"Blair, I want you back," he pleaded, turning on the puppy dog eyes. "I'd go back in time and stop myself from doing it if I could. It was stupid mistake. I wish I'd never done it!"

After his short monologue, Blair just stared disbelievingly at him. Then, out of nowhere, she began laughing. She clutched her stomach and bent over, holding the staircase for support.

When a few minutes of delirious laughter passed, she wiped a few tears from her eyes, and sobered up. "Wow, Nate. You haven't lost your touch at humor in the slightest!"

Now, it was Nate's turn to blink in surprise. "That wasn't a joke," he said slowly. He was a bit worried Blair had finally snapped and might want to kill him spontaneously with a butcher knife if he wasn't careful.

However, with how angry he made her last night, killing him with a butcher knife was highly possible.

Blair's brown eyes narrowed. "Well, it better be. Because that could be the only possible way that you could ever say such a thing to me after what you did."

Nate's palm began to sweat and his hands continued their previous wringing at an alarmingly fast pace. 'I can do this,' Nate thought. 'Blair loves me. She'll forgive me like all the other times.' However, he couldn't help but think that maybe she wouldn't.

"Bu-but Blair, I love you!" Nate exclaimed.

Well, maybe he didn't love her as much as she did him, but he could learn to with time. He just needed that second chance. It was his only hope for survival.

"Well, Nate, I don't love you. How could I after you slept with my best friend?" Blair replied through gritted teeth.

Nate could feel himself loosing the battle and fast. He frantically thought of something else to say to get her in love with him again. He had not really thought past the monologue, actually. Nate thought she'd be at his feet by then. It was meant to drive her romantic side wild.

In a last ditch effort to get her sympathy, he fell to the floor on his knees in a dramatic flourish. He raised his hands toward her in a prayer position. "Please, Blair. Forgive me. It was a moment of weakness. I couldn't help it!"

Blair's mouth dropped. Uh-oh. 'Maybe it wasn't the best thing to say...' Nate said in his mind.

"'It was a moment of weakness'?" Blair quoted angrily. "Well, Nathaniel, you should have left and gone home! Go and take a cold shower! I do not effing care! But you should've have said no!" she shouted with all her strength.

"Did I even crop up in your mind at least once?" Blair continued her rant, moving around her arms to demonstrate her point. "Did you have no little voice in your head that says 'Wouldn't Blair be just the tiniest bit upset that you're about to have sex with her best friend?'

"Obviously, I didn't come into your mind because then you might have stopped and not slept with Serena. What really gets me, though, is that you have the nerve to pop up, unannounced, and plead for my forgiveness. How could you do such a moronic thing to me, you heartless asshole?" Blair shrieked.

But Nate couldn't speak, nor would he have answered the rhetorical question. He could only stare, in fright, at the onslaught of anger radiating from the petite brunette.

"You know what?" Blair asked, her frigid timbre returning.

"What?" Nate squeaked, finally finding his voice.

"I think you should leave. For good, Nate," she said with a tone finality.

Nate nodded and hung his head. He walked back toward the elevator and was about to press the button when he heard a sound. He heard the small, weak and pitiful voice of someone saying, "Wait".

He turned, wondering who could sound so utterly sad. Nothing in the world could have prepared him for what he saw.

Blair Waldorf, with her shoulders slumped and eyes filled with tears. Her lower lip was trembling and she was holding on to the banister for support once more. However, this time, it was to control her tears. Nate could plainly see that her vulnerability lay bare in front of him and it truly broke his heart.

"Before you go," she said in a wobbly voice, so different from the voice she had in the beginning of the conversation. "I need to ask; it's killing me not to know. Was she worth it? Was Serena worth losing all we had built up?"

Nate wanted to run to her and tell her that 'No, it wasn't worth it.' But he just couldn't. He just stayed still, saying nothing.

Blair lowered her head in defeat. "That's all I needed to hear."

She then dissolved into shaking sobs that would make a dastardly villain feel sorry for her. She let go of the banister and fell onto the lowest step, putting her head in her hands. The tears rained down on the floor.

Nate knew it was time he left. He pushed the button for the elevator and got in. As he rode down the floors, he couldn't help but wonder.

Was Serena really worth losing all he had with Blair? He still couldn't come up with an answer.

Nate walked out and into the lightly falling rain outside. Looking up at the grey sky, he knew one thing.

He would keep trying until he finally got Blair back. It was only, after all, only his first try.

Fin

A/N- Did anyone but me think that Blair gave in too easily? That it was a totally OOC move? Whatever; I'll just have to get over it. Anyway, review, please!