Author's Note: Thank you all to those who have decided to read this story, I appreciate all feedback. I've been an off and on fan of Gossip Girl mainly because of the storylines. I just recently started watching and I absolutely love Blair and Dan together. I was a big Dan and Serena but I think that Blair and Dan could be the saving grace of the show…no offense to any Chuck and Blair fans. So I added some of my own stuff because I'm not as familiar with the characters like I used to be but I've gotten the gist of it down, and I added a character by the name of Ryan so Dan could have a male friend to talk to about his love life seeing as Nate is into Serena and is Chuck's friend, I felt he wouldn't be a good objective friend for Dan so I just created one. I hope you enjoy the story and I look forward to feedback so please give some.

Chapter One- About Last Night

Entering into the room, the brunette quickly stopped cursing at herself as she was assured by her doctor's arrival that hope would be in sight for her now that medical attention was here. Looking over her chart once more hoping that he would have a better understanding as to why she was here in the first place because there was nothing on her charts that proved to be pressing, but since the Waldorf family had been long time patients of his he knew that he had to at least hear her out. Taking a seat on his stool he couldn't help but notice the overly expensive attire she wore but then again her family was loaded so for her to be draped in diamonds and actual pearls was nothing new but it always did surprise him about the Upper East Side life style. In one quick faint motion, she laid back on the examination table as it all just became too much for her to even conceive, it was all one big nightmare that she felt she was piecing together slowly but surely and what little she had to go on wasn't making her feel any better.

"So Blair, what brings you by? It says here that you wanted to get tested for head injuries" The doctor said "But yet you have no recent accidents to back up your suspicions of having a head injuring" he said

"Believe me when I say, there is something wrong with my head" Blaire quickly stated "Aren't you suppose to appease the patient, is this what healthcare is offering these days?" she said

"In order for me to warrant all these fancy tests to examine what you suspect is wrong with your head, I need something that is concrete that say you could possibly have a head injury" The doctor said

"I don't care what the price is, I don't care how useless it will be, I just need to get my head looked at because no way in my right mind would I ever do what I did…with him…last night" Blair said as the doctor looked at her with much confusion

"So let me get this straight, you fear something is wrong with your head because of a decision you made?" The doctor asked

"I don't want to talk about it, I just want to get tested" Blair stated

"Start talking Ms. Waldorf" The doctor quickly replied causing Blair to be a little shocked by his tone of voice with her

"You can't speak to me that way" Blair said

"Will you please just come out with it all ready?" The doctor asked

"I'm warning you right now that after I tell you this that this will more than likely warrant my request for testing. My affairs are in order so if it should be something serious please tell Darota to inform the family accordingly" Blair said…..


[Flashback to the Dreaded Morning]

Feeling the sun shine upon her face, her eyes began to flutter open to see that she wasn't in her own room…she wasn't even in her own bed. Hey eyes began to widen as the thought of being with someone else at their place began to set in because this just wasn't like her, it was more like Serena, but not a Blair thing to do. Looking at the white cotton sheets that covered her body she immediately started to hyperventilate just by the simple fact that she was laying on such common sheets. Slowly rising she felt his hand resting on her waist and by the look of the arm she feared that he would be a hairy beast. The movement beside him caused him to stir awake which only made him feel the massive headache that he was sure he was going to get after drinking so much the night before. Both slowly sitting up in the bed, Blair turned cautiously to see that it was her worst nightmare come to life. Each falling off the bed in complete shock, they scrambled to cover their bodies.

"What the hell are you doing naked!" Blair yelled

"Clearly we….no, no. We couldn't have" Dan said beginning to realize that she was fully naked just like he was

"We're both naked dumbass. Clearly we have" Blair quickly replied "Oh, God. I think I'm going to be sick" she said wanting to throw up

"Yeah, well I'm not getting a great feeling about this either. How did it even go from movies to us being…naked?" Dan asked as he slowly rose to his feet causing Blair to look away

"Stay down Humphrey, at least let me get dressed first" Blaire said

"Then go" Dan replied "I've got to meet my dad in a few hours" he said as Blair gathered her clothes

"This is just the most God awful site. My wardrobe lying on this grimy floor" Blair complained

"Yeah, well I'm not feeling overwhelmed with joy either" Dan replied

"You probably drugged me for all I know, so please just shut up!" Blair replied

"Don't tell me shut up, you shut up" Dan fired back

"Oh, that's really mature" Blair said as she got up from the floor with the sheet wrapped around her body as she tried to find the bathroom from inside his bedroom "Where the hell is your restroom?" she turned to ask

"I don't have a restroom in my bedroom" Dan told her a little annoyed that she just instinctively thought everyone's room should have a bathroom in it, she probably even thought that everyone should have their own wing for their room he further thought

"Then where is it! I don't live Brooklyn" Blair said as Dan rose from the floor causing Blair to shield her eyes away from his nakedness. Noticing her shying away from looking at him, Dan just rolled his eyes and showed her the way to the restroom as she followed with distance close behind

"Do you need the maid to clean you or can you manage?" Dan asked as she entered the restroom

"And to get Brooklyn germs on me, I think not" Blair replied before she slammed the door in his face as Dan just had to bite his tongue from saying anything else to her

"I had to be some sort of drunk to sleep with that" Dan said to himself as he just shook his head in disbelief

"Eww!" Blair screamed out from inside the restroom while Dan walked back to his bedroom rolling his eyes in annoyance. Grabbing a pillow he almost felt the need to smother himself as the very idea of even having sex with Blair Waldorf was just like being in his worst of nightmares.

[End of Flashback]


Staring down at his coffee he began to mix in the desired crème and sugar. To say that things were crazy would have been a lie, but in the course of one night his whole day had just been turned upside down and he had no clue as to how it got to that point. Taking his coffee and heading over to a table off in the corner of the diner, Dan wanted to try to focus what little attention he had onto his writing as opposed to the attention seeking Blair Waldorf but before he could even pull his lap top out he was soon joined by one of his classmates, Ryan O'Neil, one of the very few friends he had made that wasn't so privy to all his high school drama that was the Upper East Side but did know Blair from occasional run ins.

"Coffee sounds really good right now. My head is spinning" Ryan said as he grabbed a seat across from Dan "Work this early in the morning, your dedicated" he laughed

"More like trying to get work or internship" Dan said

"What happened to W magazine? That was a good spot" Ryan asked

"That didn't pan out well" Dan said "So what's up? How was your night?" he asked his friend

"It was hello good. Twins to be exact" Ryan laughed "What about Blair and you?" he asked

"What about Blair and me?" Dan asked nervously hoping Ryan hadn't found out about last night

"I saw you two coming out of that French movie theater place, which by the way has so many subtitles. You came with to the bar but then you two snuck off, what'd you two end up doing?" Ryan asked as Dan began to cringe as the events of last night were slowly coming to him

"Nothing. Nothing" Dan lied

"Nothing? Then why did you leave early?" Ryan asked "You could have gotten lucky last night with the frisky girls I was dealing with" he smiled on at his friend

"Yeah, Blaire had an early day and then I just came from seeing my dad. It was all a lot" Dan babbled making it obvious that he was lying

"Your lying your ass off" Ryan laughed "Don't tell me Blair started getting frisky" he joked but immediately saw that Dan wasn't laughing along with him causing him to look on in surprise "You didn't!" he said

"Ssh!" Dan replied looking around hoping that no one with a cell phone or text or anything that Gossip Girl can receive information from was in the same vicinity as them

"You slept with the stuck up princess?" Ryan asked

"Not by choice, I think. All I know is we had a few drinks and then bam! We're waking up naked and together" Dan said

"You clearly had to be drunk because there is no way in hell Blair would sleep with you or you in reverse with her" Ryan laughed "You two are as about as opposite as can be" he said

"Tell me about it, which is why its all so confusing. I mean of all people why did it have to be her? I feel like I was taken advantage of or something, like I've had to endure a dramatic experience" Dan said

"Was the sex even good?" Ryan asked

"I don't even remember the sex" Dan replied

"How do you forget the sex?" Ryan asked

"When your trying to forget the person" Dan said


Pacing the floor nervously, Blair tried her best to remain focus on the task at hand which was to just be happy that she had a great day at her internship and to just forget the horrible night before. It would have been easy to do so if she wouldn't have to meet up with Serena later for dinner, ever since the phone call she felt as if she was on this test to challenge herself to tell her best friend that she slept with the guy she still could be in love with or to not tell her and hope and pray that this doesn't blow up in her face like back in high school when she slept with the wrong guy. A part of her wanted to blame Chuck even though he had nothing to do with this, but if things weren't so messed up between them and they were actually normal like a couple that love each other would be then she would have never slept with Dan regardless of how drunk she was. This had to be Chuck's fault in her mind she thought because only he could do something like this and be okay with it the next day. Tearing Blair away from her thoughts, Darota entered her bedroom bringing in fresh clothes to put away.

"Darota, sit. We need to talk" Blair instructed her long time maid and family friend as she did as she was told after closing the door behind her.

"What is wrong Ms. Blair?" Darota asked "You have been acting strange since you have returned" she said in thick accent

"Darota, I have done something unconceivable. I have done something that I can not even fathom beyond words, something that I should be tarred and feathered for, something that no respectable girl of my stature should ever do, something that will be a tarnish on my reputation until the day I die, I have pulled a Serena" Blair said

"What does that mean?" Darota asked a little confused

"I slept with someone totally beneath me while I was clearly on not a good state of mind" Blair said "And the worst part about it is that I slept with someone that I shouldn't have and it would hurt a friend" she said

"Who?" Darota asked

"No, I can't tell because if I say his name than the nightmare is a reality" Blair said

"Ms. Blair, your clearly upset and I can't help unless I know the whole truth. If it was Mr. Chuck than maybe it's a sign of reconciliation between the two of you" Darota said

"No, it wasn't Chuck. I almost wish it would have been though even though we're far from reconciling. There's still a few chickens he hasn't clucked in the Upper Eastside" Blair replied as she flopped down on her bed "It was Dan Humphrey" she sighed as Darota looked at her with shock

"Mr. Humphrey, but you two don't mesh" Darota said surprised "I mean you two are very bickery together" she said

"I know, and its why its so confusing as to why I would…you know" Blair replied

"Were you overcome with loneliness?" Darota asked

"No, it was the alcohol. In this case you can blame it on the alcohol" Blair sighed "And now I'm having dinner with Serena and I'm trying to think of how I even tell her" she said

"You want to tell Ms. Serena?" Darota asked

"I should. She's my best friend" Blair said "I have to" she continued on

"I'm one for telling truths but not when it hurts someone. I mean you have no feelings for Mr. Humphrey so are you really sure this is wise?" Darota asked

"Darota, your asking me to lie to my best friend? Of course I don't have feelings for Humphrey he lives in Brooklyn for crying out loud" Blair said

"I just simply think that some things are best taken to the grave if you can avoid them" Darota said as Blair entertained the thought for a bit in her mind

"What if Humphrey feels all emo and decides to tell her the truth thinking that would inspire some loyalty out of her? I'll come off looking like the conniving bitch in the scenario and I'm only that when I choose to be not by accident" Blair asked

"Then you talk to Mr. Humphrey, I'm sure he doesn't want to hurt Ms. Serena either" Darota said as she picked up Blair's phone to hand to her

"This worries me that your suggesting lying when your usually all pro-truth and goodwill, yada yada yada" Blair said

"Call him Ms. Blaire" Darota told her as Blair reluctantly dialed his number and within three rings he picked up the phone

"What do you want Waldorf?" Dan answered the phone

"Hello to you Humphrey" Blair replied annoyed with his greeting "We need to discuss what happened" she said

"I rather not" Dan replied

"As do I, but in the matters of Serena. I think we should talk about her" Blair said catching Dan's attention

"Oh, what about Serena? Were you planning on telling her? You know what happened" Dan asked nervously

"I'm having dinner with her tonight and I did debate the idea. I just wanted to know if you had any intention on telling her?" Blair asked

"To be honest…I know this will make me seem like a jackass because I do want Serena and I to work but I don't think I want to" Dan said

"So no telling Serena?" Blair asked

"Were you planning on telling her?" Dan asked

"At first I was but under much advisement I've come to realize it might not be necessary, and since you two are at a stand still and I with Chuck…it should just remain between us" Blair said

"Yeah, I mean it was a mistake. A mistake we would never make in our right minds" Dan said

"Yes, definitely. Then its agreed, we focus on our prospective relationships regardless of how they are currently stagnant but nevertheless we focus on them. Forget about last night, and throw it away" Blair said

"Yes. That sounds like a plan" Dan agreed

"Okay, then there you have it" Blair said before she let out a sigh of relief before they ended the phone call feeling a bit at ease that Serena wouldn't find out about their night together, at least from them.