The beginning of the story picks up as a flashback, which is taking place as kind of an alternate 3x22. As always, I own nothing, and have taken creative liberties to create a story I want to explore with the characters we all know and love. Hope you enjoy! Will hopefully update soon. Xoxo, M

Five Years Earlier

Blair felt herself bolt upright in bed, a thin layer of sweat covering her entire body. The earliest hints of sun were presenting themselves through the window, and she cursed herself for being unable to sleep that night. Too much was swirling around in her mind as she laid there alone. What if I'm not making it up? What if it's true?

It had been less than a month since they had been together, but she thought she hadn't had a period in the past six or so weeks. It wasn't like she had been keeping track, though, so the uncertainty was still able to loom overhead. She'd been mentally wrestling herself for the past few days, wondering what the best course of action was. Originally, she had just wanted to wait it out for the remainder of the week. Surely, if she waited, it would come and she could relax. After all, stressing herself out in the past had always caused her to have either a light period or a late period. If she waited as patiently as possible, all would be well.

That had been the mentality three days ago, but everything had changed since then. She, obviously, hadn't gotten it yet. If she had gotten it like she had hoped would happen, none of it would matter. But it did because it still had to. She hadn't told anybody, least of all him, and the events of the day before were replaying over and over in her head as though they were the only memories she had. It was slow torture.

I'll be waiting at the top of the Empire State Building…if you're not there tomorrow by 7:01, I'm closing my heart to you forever…

She shuddered as she thought of the seriousness in those brown eyes. His eyes were lighter than hers; a beautiful, amber color that she had always found endearing. She wondered about the possibility of it being real, and she wondered if those amber eyes would prove to be dominant over her own dark orbs. She swallowed hard and felt her stomach turn. Oh no.

She had had very few conversations with her mother about what it was like to be pregnant. Eleanor Waldorf had never been the picture of maternal poise, but there had been times when Blair was younger that had allowed them to share intimate moments as all mothers and daughters should. There had been conversations about whether or not having a baby was worth the pain of childbirth (a conversation that started after Blair had fallen victim to her very first menstrual cramps). There had been moments when Eleanor had told her about her father being overjoyed at the idea of a baby girl in the house. And, at that moment, Blair could also remember her mother distinctly speaking of her extremely persistent morning sickness. Fuck.

She jumped out of bed and flew to the bathroom, immediately realizing that she could avoid taking a test no longer. Though in that moment it felt pointless, because she believed she already knew the answer.

"You have to tell Chuck," Serena said. The blonde had arrived less than a half an hour after the brunette had called her. She'd come bearing gifts of three pregnancy tests and a panicked expression.

"I haven't even taken the test," Blair said, struggling to choke down a buttered croissant that Dorota had baked that morning.

Serena crossed her arms over her chest and shifted her weight to one side. She was still standing in front of Blair's bed, her long hair tied in a messy pony tail after she'd skipped her shower to rush over to the Waldorf Penthouse. She spoke loudly then, her voice dripping with slight impatience over Blair's hesitance, "Uh, I'm sorry, but does this happen to feel like déjà vu to you, too? Or do you not remember the last time you thought you were pregnant and didn't tell Chuck?"

Blair glared at her, "Stop speaking. I don't need to be worried about him right now. He's part of the reason I'm in this mess in the first place."

"Oh, come on, B, you said so yourself; you're pretty sure this time," Serena said, sighing and sitting down on the edge of the bed, "You have to tell him. Whatever feud you guys are in right now will not matter if that test confirms your suspicions. He has a right to know."

Blair swallowed, hard, once again thinking about the conversation from yesterday. She hadn't told Serena, though she didn't know if she actually wanted to. Would that make it worse in the blonde's eyes? Here Chuck is, handing his heart to Blair on a silver platter right when she needs it the most. But the more she thought about it, the more she believed she wouldn't be able to meet him later that day. It seemed way too dangerous. They were never going to be good together, and a baby would not solve the very real problems they were already facing.

"I don't want him to know, ok?" Blair said, her face gravely serious. She stood from the bed and yanked the bag with the tests away from Serena, who was frozen in place, "After today, he's never going to hear from me again."

Serena sighed dramatically, "Ok, B, I know you're feeling dramatic right now, but-"

"I'm serious, S," Blair warned, her voice barely above a whisper, "If this is real, he is never goinng to know. I will make sure he never finds out. I'll go spend some time with Daddy and Roman in France, far away from everyone I know. I'll figure out how to take care of it."

The brunette quickly shuffled into the bathroom connected to her luxurious bedroom. The door slammed shut behind her, and the loud sound of the lock clicking tore through the sudden silence of the room. Serena's mouth was gaping, then, and she blinked rapidly several times. There was so much going through her head that had only just started when she had received the call from Blair. Her mind was spiraling. She swallowed as she imagined a small Chuck or Blair to running around the penthouse, giggling delightfully, learning how to scheme at an incredibly young age. The thought sent a stab of pain to the back of her eyes as she rose from the bed and stomped up to the bathroom door, "Blair, I know you don't mean…you can't mean…"

Blair inhaled sharply from the other side of the bathroom door. She knew what Serena was assuming. She knew that the blonde automatically assumed that Blair would simply make the problem go away with the help of a doctor who's talents included secrecy. Blair panicked, wondering how she would even feel about that option after the pregnancy tests, "Do not patronize me right now, Serena. I have no idea how this even happened."

Serena couldn't stop her eyes from rolling, "Well, that's the one thing I do have an idea about, unfortunately."

Blair straightened her posture and pursed her lips, not that her best friend could see her do so, "That….that is in the past. That is far in the past now. Yesterday was the last time I will ever see him, I'm certain of that."

"It couldn't have been too far in the past," Serena huffed, leaning up against the door. She could hear Blair messing with the boxes of the tests, the brunette's nervous breaths echoing loudly in the bathroom, "And wait, yesterday? When did you see Chuck yesterday?"

"We had a takedown that needed to be handled, nothing more," Blair said softly, dangerously. It was technically true. She had just purposefully failed to mention that Chuck proposed that she meet him at the top of the Empire State building later that day so they could figure things out for a future. A future together. The thought of it suddenly put a sour taste in her mouth as she removed each test from its box and gripped them tightly in her pale hands.

We're never going to be safe…Chuck's words still echoed throughout her body. Every inch of her was on fire and she felt her control snap. Tears stung her eyes and her voice grew shakey as she said, "Serena, I'm so scared."

Serena sighed a little longer than anticipated. She stretched one hand out on the bathroom door as if it was the equivolent of holding Blair's hand or placing a reassuring touch on her best friend's shoulder. It was the best she could do with the door still locked, "Do you want me to come in?"

Blair shook her head as she lifted her dress and prepared for the moment of truth, "Not yet." What am I going to do?

Serena sat outside of the door, the loud throbbing of overthinking in her ears drowning out the sounds of Blair taking the test. Chuck definitely had a right to know, didn't he? Especially if Blair was thinking of doing the unthinkable. Poor Chuck had never had a real family, so something inside of Serena told her that he would definitely have some strong opinions about what Blair should do. On the one hand, she owed it to Chuck to say something.

But Blair had called her in a state of desperation. Serena loved Blair without conditions, even when they were fighting. She knew that if she ever needed serious help, B would do everything in her power to make sure that things were taken care of. That's why she had bought her pregnancy tests (both times). That's why she had immediately come over without a moment's hesistation. Because, on the other hand, she owed it to Blair to stay quiet.

The minutes felt like lifetimes. Blair felt that she had lived and died several times as she waited in the bathroom, bent over the sink. Her hands were gripping each other as though she was praying, and maybe in a way she was. She was praying that time would go by faster. She was praying that, no matter what the test said, she would have the strength to not go to the Empire State building. That wasn't what she wanted or needed.

Serena's hand was beginning to perspire against the door, but for some odd reason the simple placement of her hand there was bringing comfort to herself. Blair needed her to be strong and supportive, so Serena would try her best, despite having never been in a situation like the one they found themselves in. She waited, patiently, for any sign from Blair that there was an update. She waited for what felt like hours, slowly imagining how different all of their lives would be if only Blair would do the right thing and tell Chuck.

The door was loudly and suddenly unlocked, and Serena quickly jumped back and waited for Blair to open it. The brunette did so slowly, and the look in her glassy eyes communicated the test results before her mouth did, "I'm pregnant."