A/N: Hi everyone! This is my first attempt at writing a fanfiction since my middle school days (aka a long time ago haha), so bare with me. I don't have a beta, so please excuse any grammatical errors that may have slipped past my proof reading. In this story Serena never leaves after sleeping with Nate and she's forced to deal with her feelings/the consequences of her actions.

IMPORTANT NOTE: This is heavily based on the books, specifically the prequel, "It Had to Be You". If you haven't read it, I suggest you do, or at least the part leading up to when Serena and Nate sleep together. Here's a link to all S/N moments in the prequel: www(dot)nateandserena(dot)com/?page_id=198

This story is currently rated T, but will most likely be changed to an M rating as the story goes on. I'll be sure to let you guys know when that happens!

And finally, I do not own Gossip Girl or any of the characters in this story!

Read/Review and enjoy!

Prologue - Choices

Serena van der Woodsen is good at a lot of things.

Making guys weak in the knees with a single glance? Yeah, she had been good at that for as long as she could remember. Talking her way out of a bad grade in French? Easy. (Especially after realizing that her 55 year old teacher was a pervert with a soft spot for blonds in short skirts.) Downing shots of Grey Goose like they're water? Not so easy at first, but practice made perfect. Making her beautiful best friend jealous? Apparently she was very good at that, even when she didn't mean to be.

Another thing Serena van der Woodsen is good at? Running.

It is and always had been her favorite defense mechanism. When she was 6 years old and her parents started fighting every night, she had always ran to Blair's house. When Charles Bass pushed her on the playground in second grade, instead of confronting him, she ran and hid behind the slides until the bell rang and signaled it was time to go back inside.

Serena didn't enjoy confrontation, and she definitely didn't like talking about her feelings or dealing with anything that made her uncomfortable. So she ran away from her problems. She was a runner.

Usually Serena considered herself a runner in the figurative sense. That wasn't the case today. Her long blonde hair, disheveled and matted, was blowing everywhere in the summer breeze as she sprinted down a busy New York City sidewalk. She had no idea where she was going, all she knew was that she had to run, literally run, as far away as she could from that townhouse, from them.

After her legs had carried her a few blocks away, she allowed herself to stop or more so the August heat forced her to. She stood in the middle of the sidewalk trying to catch her breath, while her mind was racing with a million different thoughts.

"Nate? What the fuck, Nate? I've been out here for like an hour with my fucking suitcase."

"Hey, move it lady!"

Serena shook her head as some middle aged business man brushed passed her. She had to get herself together. The back of her neck was damp with sweat and she was having trouble breathing. She looked down and realized that she was wearing a wool Chanel jacket in 90 degree weather. She had grabbed it out of Nate's mother's closet in an attempt to quickly cover herself up after Blair had shown up.

"It looks like you guys have been having fun…"

Blair. Blair Waldorf. Her best friend. Fuck. How could she have done this to Blair? Why did she always manage to fuck things up?

Serena felt the familiar sting of tears begin to well up in her eyes. She quickly brushed them away, threw her hair up into a messy bun and began walking back to her mother's penthouse apartment a few blocks away.

"Sorry." The word felt awkward on her lips. What was she even apologizing for? And why was it so hard to breathe? She glanced up at Nate, who was staring at her with an intensity that told her an apology was the last thing he wanted to hear from her at that moment.

"It's okay. Don't stop. I don't want you to stop."

Serena opened her eyes and tried to catch her breath. She glanced over at the clock, an angry, red 9:30 PM glared back at her. Had she really slept that long?

Slowly sitting up, she let out a long sigh. The long walk back to her penthouse had been terrible. Aside from the fact that she looked ridiculous and people continuously stared at her (and not for the reasons they usually do), her thoughts, no matter how hard she tried to steer them otherwise, always wandered back to Nate and Blair.

When she finally reached the penthouse she was exhausted, both mentally and physically. After making sure no one was home (no one ever was), she went straight to her room and collapsed onto her bed, falling asleep within minutes. But of course she couldn't even find peace in her dreams. What the fuck was she going to do?

She let out another sigh before reaching over and grabbing her BlackBerry off of her night stand. Five missed calls, and three text messages. For a second she thought about simply turning the phone off, pulling her satin pink sheets over her head and telling the whole world to fuck off.

"Coward," her subconscious scolded her. With a trembling hand, she opened the list of missed calls first. Blair, Blair, Blair, Dad….. and Nate. Her entire body unintentionally shuddered. What had he wanted? To apologize? To say that he regretted what they did? Would she be able to handle that?

Slowly, she deleted each of the missed calls and then turned her attention to the text messages.

Two were from Blair, simply complaining that Serena hadn't answered her phone/called her back within five minutes of her call. Serena smiled, remembering a time several years ago when Blair had given her and Nate a lecture on the importance of always answering her phone calls, no matter what time it was or what they were doing.

The third message was from Nate. She closed her eyes and took a deep breath before opening it. "Please call me back, we need to talk." The screen suddenly became blurry and Serena realized that she was dangerously close to crying again.

She quickly deleted the text message and tossed her phone back onto the end table before collapsing back onto her bed. The satin sheets felt cool on her skin as she laid there in the dark listening to her heart beat. She had no idea what she was supposed to do now, and if she was being honest with herself, she didn't want to figure it out. It'd be so much easier to just pretend the last twenty-four hours never happened.

Serena sat up suddenly, throwing the sheets off of her body as she grabbed her cell phone from the end table. She may not be able to erase what happened, but she could definitely ensure that she would never have to face Blair or Nate again.

She quickly dialed her dad's number and waited impatiently for him to answer. He finally answered on the seventh ring, "Hello buttercup." His endearment made her smile. Even though throughout her childhood her father was always away on business trips or working late hours, she never once doubted how much he loved her.

"Hi daddy," she began, as she continued to pace around her room. Concern laced her father's voice, "Are you okay Serena? You don't sound like yourself." Serena had to bite back a bitter laugh. He had no idea how not okay she was. "I'm fine," she lied, "I just wanted to tell you that I've decided that you're right, boarding school would be a great experience for me."

Her dad started rambling about how excited he was for her, and how Hanover Academy was an amazing school. Just as Serena was about to start pretending that she shared her father's excitement, something caught her eye. She slowly walked over to her dresser and picked up an old wooden picture frame. Tears instantly sprang to her eyes as she looked at the three little faces smiling back at her. She still remembered that day perfectly. They were seven years old and their nannies had decided to take them all to Central Park for the day. However, after being there for only ten minutes, it had started to rain. Blair began to cry that her dress was going to be ruined (some things never change) while Serena and Nate were running around attempting to catch the raindrops on their tongues. After several minutes of trying to force Serena and Nate to stop running around and convince Blair to stop crying, the nannies decided to take them to a nearby ice cream shop until it stopped raining. The picture was taken just after they were handed their cones. And even though Blair's dress was ruined, and Serena and Nate were covered in mud, it was still one of Serena's favorite memories. No matter how messy any situation had gotten they had always had each other.

"Serena, are you still there?" Serena set the frame back on her dresser and shook her head, what was she doing? She couldn't just leave them behind, they were her family and they always would be. "Yeah dad, I'm still here. But I actually don't think boarding school is right for me. I'm sorry." She cringed when she heard the disappointment in his voice. After convincing him she was sure this was the right choice for her, she hung up the phone and collapsed back onto her bed.

She could do this. Eventually she and Nate would both forget about what happened and everything would go back to normal. Blair and Nate would live happily ever after and Serena would be there every step of the way to support her best friends. How hard could it be?

Just then the familiar ding of her BlackBerry rang throughout the dark room. She glanced down at the screen and re-read the message and the sender's name three times before it finally registered in her mind, "Natie: We need to talk, I'm coming over."

Apparently, it was going to be harder than she thought.