Author's Note: So this story was a spur of the moment thought that was brought to life by many, many trips to Tumblr. I think we've all had a range of emotions, and I've read debates on what side people are on whether Team Dan or Team Blair then of course anti-Chair. I never really thought that it was so much as people hating Blair, but I think overall from my perspective and my own feelings, it was dissappointmetn in the character of Blair. I wanted to do a story that showed her evolving in a way that the writers won't let her do. I've written other fanfictions on this board, but I think this story is different from what I've done.

It'll be shorter. 10 chapters. In Blair's P.O.V. as she deals with life's lessons. I'll be uploading the whole story, so this is the only Author's Note that will go along with the story. I hope that you all will review each chapter and I hope you enjoy the story.

The Waldorfian Conundrum

Chapter One-

August 2012

August 6 , 2012:

Diamonds aren't always a girls best friend. I don't know who came up with that phrase, probably Marilyn Monroe if I give more thought to it. Looking on at the package he's sent over, it's clear that he won't be returning from Caico's. I'd like to believe that I was making some bit of progress with him, but when it comes to Chuck Bass, it's always a momentary thing with little influence on the future. The summer has been spent chasing down minimal clues that Jack's picked up at local burlesque clubs while Chuck, who's more than eager, charters jets to follow. Convincing and trying to prove myself to Chuck has served to more of a task than trying to get the swing of running my mother's company. I welcome any chance to return to New York as I'd rather spend my nights alone in a place called home than in a suite full of gifts promising to have some time together.

Dorota is elated to have me back as I show her numerous pictures of the islands I've visited. The pictures show off the scenery, but the more Dorota flips through the pictures, I begin to realize there is not one picture that shows us. I remember where and when I took the picture, then I remember him sitting a few feet away on the phone with one of Jack's lead. Seeing the pictures, it makes me feel the loneliness I tried to push away as even being next to him made me feel like we were miles apart. Cyrus saunters in and wastes no time in hugging me, while I try my best to keep myself upbeat since the fifteen hour flight has seemed to catch up to me.

Later that night, I sit up going over files that seemed to be written in a different language to me. I thought fashion was a universal language with only one meaning, but clearly I'm struggling with this. Letting out a sigh of frustration, I lay back against the headboard. Closing my eyes, I like to drift off into my own paradise that is filled with every Breakfast at Tiffany's imagery to be imagined. Hearing a chiming sound come from my computer, I reach over to grab it to see that Gossip Girl has updated her page. The tracker shows that Humphrey is in California. What would he be doing in California? I shouldn't concern myself with worry over Humphrey because he's made it clear that he's upset with me. Maybe time has helped things? Maybe he's understood why I did what I did? I ask myself for what might be the millionth time in the span of three months.

Humphrey has managed to fall off the face of the planet. The only update I've seen on his status is a picture of him with his ex-Olivia. Tabloids have her engaged to some hockey player, so I doubt they're sparking up anything romantic. That's if I thought about it. His hair was as unruly as ever. I could only imagine how far away a brush or comb is from him. I must've looked at that pictures a millions times to the point where I saved it on my computer, you know to make sure that my computer was saving the other pictures I was uploading.

The day ends like it's begun. Alone.

August 13, 2012

The annual White Party is coming up. Feels weird to get an invitation when I'm no longer friends with Serena and now that Cici is dead. My mother tries to convince me to go, but I just don't see how I can. The very fact that I could run into Serena makes me a bit unwilling to entertain the thought even more. Chuck tries to encourage the idea as a means to look in on Bart. Me spying on Bart Bass, that doesn't sound like anything I would be interested in and the fact that Chuck suggests that only upsets me. Chuck and I go back and forth on the subject, but we ultimately agree to give each other space for the week. It's best that we give each other this space because I'm beginning to see that Chuck is reaching a dead end in the search of uncovering Bart's secrets.

Gossip Girl updates the page again, and I don't want to look but I find myself looking anyways. The tracker conveniently manages to go to Daniel Humphrey, which I'm sure is by accident with a bit of assistance by me. Still in California. San Jose to be exact. It's been a week in California, must be a writing gig out there that's he working on. He's probably found a diner, where he can spend most of his days writing while sipping on an unlimited amount of coffee. Once he got in his headspace, there was no pulling Humphrey out. I find myself hoping that he's okay in San Jose. Sounds dumb, but I can't help but worry in this moment.

A part of me begins to think about what Rome would've been like. I've entertained the thought before of eating the food, seeing the amazing sights they have to offer, among other things that Rome has at it's disposal. I shake the notions out of my head as they all seem like wishful fulfillment because at the end of the day, the decision was made. Whether it was my honest choice, it was a decision I went along with. I don't want to go over the past because it makes the present even more lonely.

Tonight, I decide to watch something out of my usual movie comfort zone. Monty Python and the Holy Grail. I need a laugh. I need something.

August 20, 2012

There have been rumblings through out the Upper Eastside of a scandalous tell all book coming out. I don't give it much merit because there's always something about the Upper Eastside coming out from those that think they know all the players in this part of New York. My mother seems to be interested in finding out, who gets raked over the coals, but I find it amusing because she usually doesn't entertain stuff like that. I can tell her down time is becoming spent with useless tabloids as she's in and out of the penthouse. I have half the nerve to just literally ask for the title of the house to switched over to me so that I can say I own something outright. I think of doing that for my own personal reasons, but I find winning the board over is becoming more tiresome than I had anticipated.

Chuck stops by and he arranges for us to have dinner. Chuck's putting on the charm, which I do enjoy a bit but in the back of my mind I know something is up. I try to ask him for his advice on the board of execs, but he simply rubs my ego and tells me I'll find a way or telling me what to do would diminish the idea that I earned it. I find that to be stupid because I did earn it, I earned every bit of right to…yeah, I eventually get the point that I haven't earned anything. I'm just running around pretending I'm powerful. Ultimately, I hate that he's put such thoughts in my head, but Chuck has always been one to divulge truths, even the harsh ones.

We have sex, which is what we're best at, but it feels like even that isn't as satisfying as it once was. The thrill of not being together, us against the world, the epic passion we have for each other. That all seems to be gone because we have each other, the world stopped caring us being together or not, the passion has turned towards other things in our lives. He sleeps while I stare out the window, wondering…what is Rome like in July?

Sleep comes hard to do , when nothing but thoughts run through my mind. Chuck sleeps peacefully as he can't even tell I'm not beside him anymore. I sit in front of the computer screen on the Gossip Girl to see that he's no longer in California. He's nowhere. I rub my eyes a bit more to see if I'm dreaming, but it's true. He's no longer on the grid. I refresh the page to see if something new will pop up. Nothing. I close the internet down, then log on again. Nothing. In this moment, I wish that I was better with computers because it has to be a computer problem for him not to even register on the screen.

I don't know why, but I worry more. I sit downstairs in the dining area with a cup of tea as I just worry. I worry about losing my mother's company. I worry about not earning my position of power. I worry about what people think of me. I worry…I worry about him. I just worry and I hate it. Feeling like I'm being overwhelmed with worry, I get up from the table and immediately grab my coat from the closet.

The cab driver probably thinks I'm crazy as I just sit in the car for twenty minutes now. The driver asks if I have any other stop to make or if I plan to get out, but I tell him that he'll get paid either way so let me be weird. I look up at the room to find that the light is still out. It's been almost three months and still the light is out. I feel a sense of calmness sitting here as if being near the place I once received my strength. It goes to forty five minutes on the meter, that's when I realize that I have to go. I don't want to, but I have to.

The worrying stops for now, but I fear it will only continue.

August 27, 2012

The rumblings continue. What started out as just minimal talks, have now gone into rampant whispers within the Hamptons. I originally have no plans to go to the Hamptons, but mother persuades me into going. The past couple of days, I've watched my clout as CEO of Waldorf dwindle by the minute. Whispers around the office pick up and I find the key phrases "She'll only go as far as her money takes her" or "Being a leader means you work up the ladder, not inherit it" as my two faves. Note the sarcasm. I tell Chuck about them, but he doesn't think much of it because it has nothing to do with our overall goal, taking down Bart Bass.

I find drinking to be comforting. I know, drinking never goes well for me, but I need it. Most of the board is here, and their nasty comments even manage to travel with them. It's like they packed it away especially for me. So in order to deal with them, I drink. I drink everything. I drink anything. I just drink as I walk the streets. Chuck sends a car for me, but I pay the driver to park the car and call Chuck to tell him I'm shopping like crazy. The last thing I need is to talk to Chuck right now. I will eventually, but not now. Not with how pathetic I feel in this moment.

Stopping off at the local malt shop. I get a double scoop of gelato just for the hell of it. I've become obsessed with dieting, but not as bad as I once was with my bulimia. No, this gelato will serve as my comfort in this moment along with this winding path that I've decided to take. The lighted path attracts me along with the waterfall in the center of the garden area. I almost forget how beautiful the Hampton's are at times, but I love to be pleasantly reminded.

Sitting on a bench, I lick my gelato cone in a serious pout mode. I'm feeling like a total fat ass with how much more food I want. I wrestle with the idea of not letting my hunger pains get to me. For the most part, I'm winning but I managed to get knocked out in the final round. Just as I get up from my seat I hear the late night run of the Jitney from across the way. I don't think much of it, but a familiar voice has me stuck.

My heart seemingly begins to break even more than what it all ready has. I see her roll her luggage away from the bus stop, but it's her turning back to what appears to be someone that she's arrived with. It's not surprising because let's face it, it's Serena van der Woodsen. It's the emergence of Humphrey that has it all feel like I'm being sucked into some sort of vortex. Tears well up in my eyes as seeing them together only makes sense. I don't care, I don't want to care. I shouldn't care. I tell myself this for the past few seconds that I have to myself before our eyes meet.

It's been three months since I've seen those eyes. It's been everything but a nightmare to see him looking back at me. Our stare doesn't last long as he once again turns to Serena and they drag their luggage on. I watch them leave along with every ounce of what I thought I knew.