Chapter Two- Heartbreak City

[Dan's P.O.V]

Usually out of the day I'm somewhat inspired by the day's lecture that I at least try to implicate it in my own life but today I just feel like I had no connection to the material. Professor Harbing spoke on and on about "doing something that was wrong that could feel so right" and for some odd reason I just kept imagining my sexual encounter with Waldord. I didn't want to think about it because lets face it we're sworn enemies, I'm Brooklyn and she's Upper Eastside, in those terms we were like Krypts and Bloods to each other. For the life of me I tried to shake off the imaging but I had to admit to myself that the encounter wasn't all that bad if I was being completely honest. It had to be memorable for me to clearly unable to stop wandering off on thought about all the kinky things we did to each other, I mean we did things to each other that I've never even done on Serena, Vanessa or Olivia…it was like anything we were game for we did. Maybe it was the alcohol talking or maybe we were just living out our darkest fantasies with each other because we in some way wanted to torment each other. To do something so wrong that felt right, I did it but I can never do it again, for the sake of my own sanity it could never happen again. Coming out of my last class for the day I had to make a quick stop by the bookstore to grab a book for my next semester classes and I was surprised to see Waldorf sitting off in the coffee shop reading. Usually this would be the part where we meet up and do our usual banter as we discuss literary topics that were brought up in class, but now….things were weird. Me avoiding her would have only added to the fire that things were weird and at this point I wanted things to go back to normal. Luckily the lines were long in the bookstore so I had a valid excuse to walk over towards her, but I just hoped this wouldn't be too weird.

"Waldorf" I said clinging on to the available chair as she nonchalantly looked up at me like I was the scum on the bottom of her shoe "Can I sit?" I then asked her

"If you must" Blaire replied in her arrogant and prissy tone that I had grown accustomed to

"How were your classes today? Harbing had an interesting topic" I told her easing right into conversation so no moment of awkward silence would come between us to start with

"They were so so. My feminist class I thought the girls were going to rip out their vaginas and raise it up like it was the new flag…some things in college are taken to seriously" Blaire replied as I couldn't help but laugh at her extreme

"Though it is a great class to meet girls" I teased her

"You would say that Humphrey seeing as everything since Serena has been a downgrade" Blaire stated "Vanessa was your lowest" she then said

"Hey, don't judge me for following my heart and not my eyes on occasion. Maybe if you lived by that creed than maybe you'd figure that Chuck is far out of your league" I told her

"And yet again I'm reminded of how little you know me, Chuck is more than my type…he's my only type" Blaire said "We love each other and that's all there is. What's your excuse for Serena?" she asked

"Uh, I love her and I've always loved her since the moment I saw her. That's far different from losing your virginity to a guy in the back of a limo then magically fall in love with him" I said "My love has been the premise of movies" I then pointed out

"Aw, I knew there was a reason why cinema sucked these days. We're forced to live the on going saga of Dan Humphrey's of the world" Blaire laughed to herself

"Yes, we're forced to see the American love story, the wholesome good boy getting the proverbial unattainable dream girl" I shrugged "Glad to see we could get back to this…with the whole you know happening" I told her after it dawned on me that we were completely back to normal and in some way she had cured my repeated thoughts of that heated night

"Yes, because I've forgotten. That night never happened nor will it ever happen again" Blaire smiled "You have your respected relationship with your proverbial unattainable dream girl that seems to constantly be on halt…" she said before I had to add my two scents in

"And your delusional relationship of what love should be about" I laughed

"We're both occupied now, and there is no need to look back" Blaire said before she teasingly took a sip out of her cup that looked somewhat seductive to me "I take it you'll be attending the Thorpe dinner party tonight?" she asked

"My dad has all ready informed me, and that has yet to be decided. I wanted to stay in and attempt to write tonight" I replied "You?" I then asked

"Do you even have to ask? Eleanor styled half the guests at the party. You should come, it could be a pathtic attempt to spend time with Serena" Blaire said

"It could be, but then it could be a pathtic attempt for you and Chuck to rekindle your hazardous relationship" I smiled back "I really need to write, and these events circulate every week" I laughed

"Spoken like a true common person" Blaire laughed

"Common, really? Well I strive to be common then while I try to write the greatest piece of literature known to man" I declared

"And insane" Blaire laughed

[Blaire's P.O.V.]

I'd be lying if I said that I didn't think about my encounter with Humphrey, I mean I tried to stop but I just can't stop it. What's wrong with me? I want to pull my hair out for crying out loud. My nights are plagued with the images of him relieving himself of his shirt to show off his well sculpted chest as I lay beneath him in somewhat of a haze that he could look so good underneath the thrift store clothing. I can see that night so vividly that I swear I'm having an orgasm in my sleep the same points I had them that night, even at points where it just felt like mind numbing foreplay between us. I remember thinking that I had experienced the highest of sexual peaks with Chuck Bass but it was Dan Humphrey that had taken me to the highest of peaks. That in itself was revolting and angered me because if he knew what I genuinely thought than that would make him more pompous and know it all than what he all ready is. Sitting in my mirror brushing over my hair like it was worth millions and millions of dollars, which lets face it, it should be, Serena came crashing into my room flopping onto my bed like she had ever since we were little kids in thousand dollar dresses. Quickly I rid my mind of all things Dan Humphrey feeling like it was a sin for me to think about him in Serena's presence. Turning to look back at the blonde I saw that she was overcome with joy which might have to do with Dan, but who knows these days when it came to Serena.

"I spy a happy S, what has brought about this?" I asked her

"I'm just uber excited about tonight, which is surprising seeing as we've gone to these events since we were young" Serena told me "Tonight is going to be perfect" she beamed

"Oh, and what will make it so perfect?" I asked her

"Because I've finally gotten Ben to agree to go with me on a public date. I think he's been fighting his feelings for the longest but now he's willing to try" Serena smiled as I looked at her a bit confused as to when Ben became her latest conquest

"Ben? Since when have you been courting Ben?" I asked

"Since he's been cleared of what he was wrongfully accused of" Serena stated in response "He has a fresh start and he's finally letting himself live for a change" she said before I let out a forced laugh in amusement

"Ben. Ben. Okay, this is confusing me Serena. Ben still tried to kill you, he was aware of Juliet's scheme which means that he's still ultimately a part of the bad side" I told her hoping that this would register to her how stupid it would be to go with a guy like Ben

"So you keep saying. Blaire will you be happy for me" Serena said

"You've said that plenty of time and I've attempted to be happy for the millions of time, but S, let's be real here" I told her "Your mother is going to have a coronary when she see's Ben draped on your arm" I then said but it only made her scoff at the thought of her mother being a determining factor on her relationship with Ben

"Ben will be fine, and we will have a great night" Serena stated as if she were growing annoyed with my continual questioning on him

"What about Dan? I mean it wasn't long ago that you were all goo goo over him and the possibilities of getting back together. I thought you chose him over Nate?" I asked her

"Dan and I have agreed that now isn't our time. We didn't want to rush into anything" Serena quickly replied

"So you rush into a relationship with Ben? S, slow down a bit…I mean think about how Dan will feel about this?" I said

"Since when are you an advocate for Dan?" Serena asked "And I'm not even with Dan" she said

"But this…this is the guy that tried to hurt you, Dan will be beyond pissed I would think" I told her before she quickly got up from the bed and straightened out her clothes showing that she had reached her limit

"Look, I was hoping I would get support from my best friend but I'm clearly not going to get that. All I wanted was your support not the doubts, I know what this will do to Dan but I've got to follow my heart" Serena said

"Fine, if you want support then….support" I sighed knowing that with that statement it was clear she was beyond selfish and I was semi-relieved that Humphrey wasn't intending to come tonight so that he wouldn't see the display I'm sure Serena was going to put on for her new beau.

[Dan's P.O.V.]

I literally put time aside, I mean literally put time aside to focus purely on my writing. I ordered a pizza so that I could eat slice after slice without being obligated to use a plate, which would force me to clean and cleaning was the last thing I needed to do. The greatest thing about having the loft to myself now was that it was my own little bachelor pad, of course I have the occasional family picture hanging up but mostly it was my bachelor pad now. But back to my writing, yeah, that's not going anywhere. I got about three sentences down on the paper but quickly reached a brick wall and just couldn't manage to get past it. The thought of seeing Serena began to flood my mind at the Thorpe Dinner party, maybe it would have been nice to have an evening out with her. Since she had returned from her mission to save Ben things had come to halt after it was revealed to me that I was the one she had chosen out of Nate and I. Just the thought of Serena had me all ready up and about the loft trying to pull together my best suit and tie. Within a New York minute I was making my way up the steps of the Met and could visibly see the extravagance of the event as he made his way over. It was always a surprise to him that he was on the list to get in because for the longest he had always heard about these types of events but never did he think he'd be a regular to them. Spotting Chuck off in the corner with his latest conquest in a compromising position, I didn't want to waste my time trying to see who the girl was when I'm sure she'd be replaced by the following day let alone week. Just as grabbed a champagne glass, I descended the staircase to see Eric coming towards me. For a moment I was glad that I didn't have to search far for company but it was by glance that I happened to look upon Serena and what I saw nearly knocked the wind out of me as she was with Ben. This was a different type of with, it looked like a together with or hope we hook up tonight with…it was heartbreaking with.

"Dan. Its not what you think" Eric told me as he walked over but all I could do was look on at Serena so much so that she could feel me looking at her

"I'll be right back" I told him as I walked past him over towards Serena and Ben. Pulling away from Ben's embrace, Serena tried to walk over towards me so that I wouldn't approach them angrily

"Dan, wait" Serena said cutting me off midway but at this point I just wanted to rip Ben to shreds and then maybe tear Serena a new one as well because I was that upset

"Wait? Serena, what the hell are you doing? This guy…this guy tried to hurt you and your what? Are you together now?" I asked her in complete disbelief

"Look things have changed. He's changed…he's not that person that my mother had put away" Serena replied

"Changed? You don't know him Serena, but now your acting as if you can speak to his heart and soul like your some kindred spirits type of crap" I told her trying my best to contain my anger but I just couldn't help it at this point "This is insane" I told her as I ran my fingers through my hair just trying to calm myself in some way shape or form

"I know. I never meant for this to happen, but I just got caught up in trying to save him and then…it just happened" Serena said

"So what you have a hero complex and you've fallen for him?" I asked her in disbelief that she would even say something like that "Do you love him like you love me?" I then asked her before she looked at me stunned that I had even asked her that

"How can you ask that? No, I'm not answering that" Serena refused but I needed to know

"Do you love him like you love me? Answer the question, if its easy then answer the question" I told her

"That's different. The way I feel about you is completely different than what I feel about him. I don't know I just can't explain it" Serena said becoming teary eyed

"Then…I'm just, I don't know" I said unable to fathom what else she could say that would make this better

"Please tell me that we'll be okay?" Serena asked desperately wanting things to be okay with us

"At this point Serena, I'm not sure…this one hurts a bit" I told her as I so desperately wanted to just leave and crawl into a ball

"Dan" Serena said trying to comfort me but I just couldn't even stand to be around her anymore especially knowing that she was with the guy who had plotted to hurt her. Breaking away from her embrace I took one quick swig of my champagne before placing it on a passing tray that a waiter was carrying

"I'm done" I told her before I just quickly turned to leave not giving her any opportunity to say anything else to me at all because at this point I don't think I had the stomach to hear any thing else from her. I wanted to get drunk, and I wanted to do so right now because right now sucked and it was all because of Serena.

[Blaire's P.O.V.]

I guess I must've missed the earlier entertainment because by the time I made my way inside the hall the room was a buzz with gossip about the latest argument between Humphrey and Serena. Seriously, if Serena thought that Dan was just going to accept that she was with Ben like it was nothing then she's more dumb than I originally thought. I don't like to think the worst of my friend but Serena had this habit of forgetting about others and what they may feel even though she's trying to satisfy herself. In no shape or form am I saint but I wouldn't intentionally hurt people like Serena would, and I just wish she'd realize what she's doing especially because I know how much she loves Humphrey. Mr. Thorpe had come to the forefront of the party and like the followers we were at the party, everyone began to gather around to hear his speech. For a while he went on and on talking about his hopes for the future and business as usual, which I was so tired of hearing about at this point because going after Thorpe was all that Chuck had on his mind when it came to Bass Industries. Just as I grew so bored that I thought I might drift off to sleep, I then heard him introduce his daughter and fiance. I thought nothing of it because I didn't know the girl but it was when she had brought Chuck up along with her that it all sank it for me. All eyes turned towards me and cell phone pads were poked at. Looking on him smile like an idiot I just felt every ounce of my heart coming up my throat and I was literally about to choke on it. Unable to take the sight of the bumbling idiot, I quickly walked out hearing my name being called out by Serena.

Hours later after trashing my room and ripping up every picture I had of Chuck and I together. To be honest I felt like I could have burned the room down because along with this room came the flooded memories of us together in here. I genuinely wanted it all to burn to hell because this is what my love for him went to…to hell. Running down the staircase I couldn't take it anymore, I had to get out of this house and I had to escape the Upper Eastside because I know Chuck's engagement was going to be the only news I'd hear or see. At first when I entered the limo I had no idea where I wanted to go but then I just thought out of the blue that no one would ever suspect that I would run away to Brooklyn. Blaire Waldorf voluntarily running into Brooklyn would be a line that I knew I would regret, but I didn't care at this point. Having the driver drop me off a block away from his loft because I knew if I had pulled up in front then it would have been to suspicious. Making my way up to the loft, I almost felt like I was beyond pathtic that I had to sneak away to Brooklyn for a friend when I was drenched with friends back in Upper Eastside, but the only person that I knew would understand this heartache was Humphrey. Taking a moment to gather myself, I then knocked on the door.

[Dan's P.O.V.]

Sitting on the floor of the loft, I looked on at a glass and bottle of whiskey just thinking how drunk could I get before I would forget that Serena even existed. I mean I literally sat there for on the floor for what felt like an hour staring a bottle. I'm such a pussy, just drink the damn thing Humphrey is what I keep telling myself in order to pump myself up to drink. Leaning forward, I grabbed the bottle and immediately began to chug away ignoring the phone calls that were coming in from my dad. I'm sure he'd come by tomorrow to check on me, but I'm not even sure I'd let him into tomorrow if it were up to me. Officially to myself I swore off and promised that I would never go back to Serena, not this time because too much hurt and pain had come between us to pretend like we could still have that happily ever after I had dreamed of. Anything I ever dreamed about Serena and I was all just a delusional fantasy that I had to wake up from or else it was just going to swallow me whole. Vanessa had always told me that it was fantasy but I just believed it and wished it true that now I wish I could go back and wish upon something else, maybe I should go back and wish for that stupid writing kit that I wanted when I was kid because that's something that could've mattered to me but instead it was wasted on stupid adolescent hopes for the hot girl, well now I don't want it. Hearing a knock at the door I hesitantly made my way over going back and forth thinking that I should ignore it but my decency got the best of me. Opening the door I was a bit surprised to see Waldorf standing on the other side with tear stained eyes. Making her way inside like she owned the place its what I half expected from her as she never respected any aspect of my privacy since the moment I met her.

"Mind if I have a drink?" Blaire asked as she picked up the bottle and took a seat on the sofa

"Are you sure that's the best thing?" I asked her remembering the last time we decided to drink together

"I've had a crappy night, a night that I want to forget so I'll deal with the consequences later" Blaire said before she took a quick swig of the drink while I resumed my seat on the floor

"What happened to you?" I asked her before she handed the bottle back to me as she layed back on the sofa

"I don't want to talk about it" Blaire replied coldly

"Okay, well your clearly upset about something because you've just taken a shot of whiskey from the very bottle I'm drinking out of" I pointed out to her for her own sanitary reasons that she always complained about

"Humphrey I don't feel like the banter, I just want…I don't know what I expected by coming here" Blaire said with a bit of sadness as if this was cursed upon her to be in my presence, to be in Brooklyn for that matter

"Then go. You don't have to be here, I never asked for your company. You just showed up, and frankly, I like when I'm alone" I fired back just as coldly not wanting to play her games nor banter

"Screw you!" Blaire yelled at me as I swiftly hopped up from my seat unable to take her prissy attitude

"What is now! I'm not going to kiss your ass like the minions, so tell me what's wrong or just get the hell out!" I yelled at her making her even more upset with how I was talking to her "I'm not them so don't think for one second that I'm going to let you talk to me like I'm some lackey" I then added

"Because you are! That's what you are and you liked it that way. It was all pity me, poor Dan Humphrey as I wish and hope for the pretty Serena van der Woodsen" Blaire taunted me

"Shut up" I said as I took the bottle into the kitchen to throw away

"It's the truth. You fell in love with Serena the first moment you saw her, give me a break! You envied her, it wasn't love. This heartbreak was inevitable, it always is when it comes to her" Blaire told me "Sorry but it was, that's the risk of falling for Serena" she said

"And what's your excuse? Your so desperate for the love Serena gets that you settle for a shrew like Chuck Bass. I mean you two are the same in every aspect that its sickening, two broken ass people trying to fix each other" I fired back with just as much anger towards her showing no sympathy

"Take that back! Take it back Humphrey!" Blaire screeched at me

"Go to hell!" I shouted before she made a mad dash towards the kitchen where I was

"Take it back!" Blaire said once again as she was now shoving me around like I was some rag doll

"What was false about that statement. Chuck Bass is a worthless piece of crap and your…you're the one that loves him. I wish I had a love story like yours" I said sarcastically and at first she took it like she always had before I noticed tears welling up in her eyes. My heart broke a little at the sight even more than it all ready was but I never meant to hurt her the way I was hurting "I'm sorry" I sighed trying to find the words to say "I'm just pissed at Serena and I'm taking it out on you, which is unfair of me because Chuck is too easy of a target especially right now" I then said

"No, its fine. It's fine because your right. I'm the worthless human that loves him…I mean that's what I am, I'm worthless for loving someone like that and to think that's a happily ever after" Blaire replied

"No, your not. He's just an idiot for making you wait, you two clearly love each other regardless of how twisted it is" I said

"Oh, wow! You really haven't been around these past few hours. You missed the big news, the news of the century apparently" Blaire said holding up her phone towards the end

"What? What did I miss?" I asked her a bit confused at to what she was talking about but secretly hoping that Ben had revealed himself to be some crazed stalker of Serena's that way Serena felt like a dumbass

"Chuck is officially off the market. He's engaged" Blaire said handing her phone over towards me as I read it in disbelief

"How the hell can Chuck be engaged? He can barely engage his mind to a subject in school" I said still finding the news hard to believe

"Well believe it Humphrey! He was all smiling from ear to ear and holding her hand like he won the damn lottery or something" Blaire fired back angrily before I just extended the bottle to her because she clearly still needed to blow off some steam. I thought what Serena had done was dirty but to marry someone that you barely even know, well with Serena it could be near knowing her, but Chuck…I never expected it

"I don't want it" Blaire said shoving the bottle away

"C'mon, you do" I teased "This is the only thing that will hold you together if you let it" I then said

"You're the last person I thought would believe that logic, that sounds like something Serena would say" Blaire replied

"Yeah, its dumb but we're both smart…we're smart all the time. We deserve to be stupid" I told her

"Maybe its because we're so together in some odd way. Us being stupid isn't in the cards because we'll always go back to being the smart ones" Blaire stated "Oh, the many night I wished I could be as careless as Serena" she laughed

"You don't have to be Serena, just be yourself. I mean what's the point of letting loose if your gonna try to be like someone else the whole time. Be Blaire Waldorf" I told her

"Be Blaire Waldorf, I don't know what that is anymore…I don't think I ever knew. I was always Blaire Waldorf, Serena's best friend. Blaire Waldorf, Chuck Bass's girlfriend or Nate Archibald's girlfriend" Blaire said

"Sometimes both at the same time" I joked as she quickly hit me on the arm unable to hold back the laughter causing her to drop the bottle to the floor. The bottle shattered into pieces on the floor which alarmed me as I didn't want her to cut up her shoes and have her bitch at me over that so I grabbed the broom and the dustpan and immediately began to clean up the mess

"I'm sorry" Blaire said apologetically

[Blaire's P.O.V.]

I was a drunken mess or at least I thought I would be at this point, I thought I was drunk enough that it would be the reason why I dropped a bottle causing it to shatter into pieces but it was just me being a klutz. Maybe I shouldn't drink because as Humphrey is cleaning up around me all I keep looking at his is how muscular his arms look or how every time he bends over his ass looks extremely in shape. Can one do ass workouts because if so then I think Humphrey does a lot of them. I have to be drunk now if I'm looking at Humphrey like he's a piece of meat, he wouldn't even be the filet mignon if that was the case. I need to stop looking at him and figure out how I'm going to get back home without being spotted by anyone because the last thing I need is to be pictured as the lonely and pathtic ex who hoped that we would work things out, but wait I was that pathtic ex I then thought. Stop looking at Humphrey I kept telling myself as he finished cleaning up. Making his way back over he leaned down to pick up another piece of glass before tossing it aside, and I swear when he stood back up we were closer than ever. The heat and the intensity had to be building in my mind because I'm clearly drunk. His eyes keep looking at me and like I thought we are extremely close to each other. Please tell me this isn't going to happen again because the sad part is that I kind of want it to.

"I should go" I said but my feet wouldn't allow me to move as we both stared at each other wondering if the other was thinking the same thing

"Yeah, you should" Dan replied focusing from my eyes to my lips as if he was wondering once again what my lips taste like

"Okay, I will" I then replied but once again my feet failed me. Looking down at my feet, Dan laughed to himself as it was obvious that I said one thing but wasn't doing it

"You want to, don't you?" Dan asked as if he needed the confirmation but he should have all ready had it by my non movement

"Maybe for tonight" I whispered softly feeling my heart jump in my throat as I began to fight for air

In one quick motion he captured my lips with his and what started out as soft and tender kisses seemed to intensify into pure animalistic want and need. Leaning against the kitchen counter we both had found our comfort in each other as I wrapped my arms around his neck so that it would be easier for me to deepen the kiss. Are tongues dueled for the longest as we each wanted to have power like we both needed it, and I have to say that I was competitive but the way he was making me feel at this moment I was more than curious to see how Humphrey would handle having the control over me. Pinning me between his arms, he took much pleasure in his control was more than ready to exert it as his lips moved to my neck and his other free hand had lifted me up so that I was sitting on the counter. Leaning my head back against the cabinets as I couldn't help but let out a moan towards the work he was doing. Quickly relieving ourselves of our shirts as I threw my blouse to the floor, he quickly picked me up off the counter and began to back me into the living room towards his bedroom as we didn't manage to break away for one second.

Falling back on to his bed, I began to think we were on a marathon sprint to see who could take off there clothes the fastest. Leaning forward he lay atop of me continuing to roam my body while my fingers ran wild in his hair. His kisses were a mixture of sweet and tender with a mixture of sweet and caring like he was at person as if he wanted me to be comfortable. Pinning my hands back I felt his hands slowly pull down my underwear as I slowly tugged his boxers down and within moments I felt him inside of me.