Summary: Set somewhere in season 3, before the whole Jack/hotel thing. In a drunken stupor, Blair accidentally tells Chuck the one secret that could tear them apart at the seams. If only B kept her lip-glossed mouth shut…

Blair Waldorf had never been a sloppy drunk. Even completely inebriated, she could still form coherent sentences and balance in 4-inch Louboutins while carrying a ten-pound Balenciaga handbag. She never blabbed her dirty secrets or exposed a scandal worthy of the New York Times front page. She was never the way-too-drunk girl who ended up bar-dancing and panty-dropping, sleeping with the closest y-chromosome available. She kept her wits about her even when heavily wasted and no one would have expected less from the infamous Blair Waldorf.

So one evening, after having a few too many gin and tonics at that night's elitist, Upper East Side bash, Blair teetered into the Empire Hotel following her sexy boyfriend, Chuck Bass. She collapsed on the plush, designer bedspread of their King-sized bed, slipping her feet out of a pair of exquisite Jimmy Choos. She hadn't reached the point of true inebriation but she was at least past tipsy.

Chuck, who was more sober than Blair, yanked off his Armani suit jacket and loosened his necktie so that it dangled mid-way down his exposed chest. He had already unbuttoned the matching dress shirt on the elevator ride up to the Penthouse.

By the time Chuck removed his slacks, Blair was left in only her rose-colored La Perla push-up bra and bikini-cut panties. Chuck's thoughts were passing NC-17 territory and reaching X-rated. He rolled her over on the bed and trailed kisses down her swan-like neck. He did always have that weakness for the hollow of her neck.

"It's good that we don't have kids, right?" Blair asked suddenly, interrupting Chuck's ministrations.

He glanced up at her, wondering why she would bring this up now. "Uhh…sure, I guess."

"Because they would ruin everything, right?" Blair continued as if this wasn't the weirdest topic they'd ever talked about.

Chuck didn't even bother acknowledging this question because by now his liquor-blurred mind was pretty sure that these inquiries were rhetorical.

Blair continued on for a good five minutes about kids and babies and Chuck pondered the possibility that someone slipped LSD into one of her drinks. The next words out of her mouth confused him entirely.

"So I'm glad I did what I did then," she smiled slightly, pleased with herself for coming to that conclusion.

"What did you do?" he asked as he shifted to one side, glad that he hadn't drank more earlier because then this whole thing would be even more of a conundrum than it already was.

"Well you know that time a couple years back with the Gossip Girl scandal and the pregnancy scare?"

"Sure." And he did, in fact, remember it perfectly. Nate punching him, Blair's impromptu almost-departure to Paris, and his own sarcasm about how smoking was bad for the child – all of those memories was forever ingrained in his skull.

"Well there's something you don't know," Blair explained.

Chuck thought about this for a second then reconsidered and decided that it was probably just some trivial detail about what pregnancy test she used or what headband she was wearing at the time. Blair had a knack for finding meaningless things important when she was tipsy.

"Yes?" he encouraged.

Her answer was muffled because she spoke it directly into his left shoulder and the fluffy pillow he was leaning back on.

"What?" he asked.

Blair flipped over onto the golden pillow next to him and nestled under the crook of his arm. A major part of Chuck's brain wanted to just tell her to spit it out so they could get back to what they were doing before this little discussion began. However, he refrained because she was handling this topic in too odd a way for the issue to be unimportant.

With a deep breath, she mustered up her courage and told him.

"I had an abortion. I was pregnant and I had it aborted."