Purely speculation and wishful thinking based on spoilers/call sheets/set photos for episodes 06.05 and 06.06. This also features an unconfirmed spoiler about Eleanor.
It was just supposed to be one scheme.
After finding out what Georgina was really up to, Dan swallowed his pride and called the one person he knew could help him get revenge. When he called, Blair seemed surprised but happy to help. She sounded so… "Original Gangsta Blair." She had told him to come to the Penthouse right away so he could fill her in on all the details.
As Dan got off the elevator at the Waldorf Penthouse he sighed to himself, thinking about the last time he had been there. When he thought things would be different. Asking Blair to come with him to Rome only to have Serena come to the interview instead. Where had everything gotten so messed up?
He'd had all summer to think about it. The constant analysis running in his head was almost more than he could deal with most days. He'd seen Blair around for the past couple of months and they had been cordial. It had been weird seeing her and not being with her - too hard sometimes. He was very much still in love with her and couldn't see a time where he wouldn't be. However, they were adults and he was intent on acting like one. All he really needed was for her to be happy.
"Dan!" Blair said more eagerly than she had anticipated.
"Blair… hi. How are you?" Dan asked, staring right into her eyes, trying to read her quickly.
"I'm good. Busy, but good."
"Yeah, I heard. Everything's going well with Waldorf Designs?"
"Yeah. It's been good I guess" Blair glanced down, her eager façade falling with every word
"Good." Dan said, still trying to read her expression. He could tell something was off but he wasn't sure what. He decided not to push it.
"Well, come in. What is Georgina wrecking havoc on now?"
"Oh, uh…"
"Darota! Bring us some tea… and scones." Blair called out "Earl Grey, right." she said to Dan.
"Yeah."
"Earl Grey tea." Blair called again "Let's sit." She motioned toward the couch.
Dan explained the whole situation to Blair who nodded and chimed in. She wasn't surprised by what had transpired, and, as always she had the perfect solution. Dan was pleased by how… mature they were being and when he stood up to leave he let out a sign he didn't realize he had been holding in.
"Well, I guess I should be going now." Dan said, standing up and reaching for his bag
"Oh? Do you have big plans tonight?"
Dan furrowed his brow and tiled his head. He wasn't sure how to react to her question.
"No… not really." He proceeded with caution "I just… figured you did. Some fancy gala or party with, uh, Chuck."
"Actually no. And Chuck's out of town. Again. At least until tomorrow." Blair sighed to herself
"Oh?"
"I was just going to watch a movie. So. Um. You could stay. If you want."
"Do you want me to stay?"
"I wouldn't hate it." Blair smiled, really smiled, for the first time since Dan got there
"Okay then. Do I get to pick the movie?"
"Of course not. When do you ever get to pick the movie?"
"Never." Dan smiled, remembering
Blair stood up off the couch and walked toward him. She looked up into his eyes and took his hand.
"We'll watch in my room. Okay?"
"Okay."
Dan followed Blair up the stairs in silence, her hand still on his. So surprised by the moment, his brain had yet to catch up with his actions.
"Get my computer from the desk, will you?" Blair said as she walked into her closet "I'm just going to change into something more comfortable."
"Okay."
Dan walked over to the desk and got the laptop, and he smiled seeing the plastic crown he had placed on her head on the MET steps right next to it. He picked it up to look at it and uncovered a stack of movie stubs from the movies they had seen together, a British flag from their coming out party, and the key from the hotel where they had their first time. Overwhelmed, he didn't know what to do with knowing she had not only kept all that stuff, but also had them on display on her desk. It filled his heart knowing it had been important to her, like it had been to him. Fearing she would see him looking through it he quickly put the crown back and picked up the computer.
"So what are we watching?" Dan asked, turning on the computer and sitting on the side of her bed
"I was thinking Breakfast at Tiffany's." Blair said from inside the closet "I just feel like something familiar. Something I don't have to think about too much."
"Well, you've certainly seen it enough times for that."
"Yes, but we've never seen it together."
Blair came out of the closet in a silk night set with lace trim. Dan had to watch himself from allowing his jaw to drop at the sight of her. He realized at that moment that he would never get over her beauty.
"Do you have the DVD?" Dan asked absentmindedly
"It's actually already on the computer." Blair said sitting down on the bed.
Dan took off his shoes and slid to the headboard where Blair was sitting. He perched the computer on his knee. Blair quickly found the movie in her library and pressed play. She put her head on Dan's shoulder and he turned his head to watch her. His arm ached to go around her but he resisted the urge.
It was only supposed to be one scheme. Yet here he was, in her room watching a movie and feeling so close. So intimate.
When the movie ended, again Dan turned to leave. He wasn't sure what to make of her asking him to stay but he certainly didn't want to read more into it that she intended. However, once again Blair urged him to stay.
"It's so late Dan. I don't want you going all the way back to Brooklyn now. You can just stay here tonight."
"Here with… with you?"
"Yes with me. Who else? Serena's not here."
"I know but…"
"But what?"
But what? He thought to himself. But what about Chuck? What about the fact that we're not together? What about the fact that you chose him over me?
Instead he said, "Okay. I guess I'll stay."
"Good." She said "You can put the computer back on my desk."
Dan took the computer and put it back on the desk, noticing again the crown. He took off his sock, pants and left only his t-shirt and boxers on. He turned off the lamp by the bed and crawled in. Blair laid on her side watching him.
"Good night." He said
Blair moved from where she had been watching him to right next to him. She looked right into his eyes and moved her lips toward his. Their lips touched, ever so softly at first and Blair pulled away. Dan opened his eyes and looked at her.
"Blair, what are you- ?" he asked softly
"Dan, no talking." She whispered, "I want this. Nod if you do too."
Dan instinctively nodded.
"Then let's not think about it."
Dan smiled and looked into her eyes. He could see she was sincere.
She moved back in a kissed him more intently and he reciprocated. Their lips crushing into each other. Every kiss more and more intense. Dan fearing every one will be the last and wanting to take all of Blair in while he can. You're being selfish, he thought but it quickly vanished as her hands went into the flap of his boxers.
He reached his hand under the silk of her night shirt and rubbed her breast with his entire hand. Finding her nipple he pinched it between his fingers and felt her moan in his mouth. He moved his kissing down her jaw line and into the crook of her neck, finding the spot he liked so much before. Blair let out a gasp as Dan became more and more hard in her hand.
Breaking apart for a second to remove their shirts, they fell into each other skin on skin. Blair kissing his heart and Dan concentrating on her neck, determined to make a new mark where the old ones used to be. This is primal he told himself but suddenly he felt a twinge of guilt and pulled away and went back to her lips.
Their bodies close together and rubbing in unison. Dan rolled Blair over until he was positioned on top, her legs around his hips. Dan removed his boxers exposing his completely erect penis and put his fingers on the sides of Blair's silk shorts and pulled them off, flicking them across the room.
He leaned on top of her, using his hands to massage her clit while kissing her with the same intensity as before. Blair was moving with his rhythm, and releasing a quiet purr that drove Dan wild.
She broke away from the kiss and whispered in his ear "make love to me" while Dan moved from his hand to the tip of his penis rubbing her clit. She was so hot and wet that he easily slid inside her and released a moan of his own on the way in.
They moved together in unison, sweat dripping, resting their foreheads, and staring into each other's eyes. Suddenly Blair's eyes grew wide and her body began to vibrate out of her control. The insanity of her orgasm sent Dan into one as well as he thrusted deep inside of her, feeling everything.
Once they had finished, Dan rolled off of her, back to his side of the bed and didn't hesitate to wrap his arm around her. She snuggled up to him and rested her head on his chest. They didn't talk; they just lay in silent contentment as they both fell off to peaceful sleep.
It was just supposed to be one scheme yet here he was, making love to Blair.
When Dan opened his eyes the next morning it took him a few seconds to realize where he was. Looking down and seeing Blair against him, naked, he realized last night must not have been a dream. A moment of panic kicked in. He had just gotten to a place of acceptance. Blair was no longer his; yet, here she was in his arms. By her choice. What did it all mean?
Before he could analyze it out of existence Blair opened her eyes, looked up at him, and smiled. Dan smiled back but found that he had nothing to say. Somewhat unnerved by that he went with it and waited for her to speak.
"Good morning." She said sleepily
"Good morning"
"I haven't slept that well in months… well, since at the. Uh, at the loft."
Dan was taken aback. He had chalked her leaving up to her not caring about him the way he cared about her. Now it didn't seem that way at all.
"No?"
"No. Chuck is a restless sleeper."
"Oh. Right." He said under his breath
Yes, that seems more logical, he thought. It's not me, it's him. I cannot get my hopes up, he promised himself.
"Sorry. I don't know why I just told you that," she said, embarrassed, "I am just so used to telling you everything. I should know better by now."
"No, I mean. It's okay."
She hadn't moved from his side and his thumb nonchalantly stroking her shoulder.
"No, it's not. I missed you." She said quietly, so quietly if Dan hadn't been paying complete attention he would have missed it
"You did?"
"Yes. It's not that hard to believe, right?"
"No, I mean. Well I guess a little."
"Why?"
"I figured you had everything you wanted with Chuck."
"It's not really like that."
"No?"
Dan was curious. He had spent all summer deciding she was happiest with Chuck but too embarrassed to admit it to him.
"No. He's..."
"What?"
"He needs me."
"Oh. What do you need?"
"I don't know."
Blair sat up in bed and reached over the side for her silk night shirt. She put it on and walked to the bathroom.
"Can you stay for breakfast?" she asked sincerely
"Yeah. Sure." Dan replied, sitting up and reaching for his boxers
"I still have a few of your things here, if you want to wear something else."
"Oh. Right."
Dan stood up and walked to the closet. Surrounded by colorful clothes and beautiful shoes where his few dark tops and pants. He smiled to himself, wondering if Chuck had seen his things in her closet. Proof that their relationship had been real. Proof that she had made room, literally, for him in her world. He opened the drawer and saw the couple pair of boxers and socks she had taken from the loft, insisting that he needed to keep clean ones at her place.
He hesitated but felt his heart swell. The same overwhelming feeling he'd get when their friendship first started. Every time she'd do something that wasn't what he expected.
She had kept all of his things, in place. She hadn't removed him from her life.
It was just supposed to be one scheme but here he was, falling back in love with Blair.
"Did you find something?" she asked, peering into the closet, covered in only a towel
"Yeah."
She smiled at him and walked into the closet peering into the drawer she saw he had opened. She reached for a pair of underwear and proceeded to put it on.
"I didn't. I didn't know what to do with your stuff. Honestly, I think I liked seeing it here. It felt like you were still here. It felt like someday you might come back."
"Come back?"
"Yeah. I know how silly it sounds. I know what happened. I just… I just didn't want to think it was over. You know?"
"Yeah. I think I do."
Truth was he still had her things on his wardrobe rack - the blue dress, the skirt with the flowers, the red silk shirt. Rufus had said he should take it down, but he had felt the same way. He wanted to remember she had been there. He didn't want it to be gone if she ever came back. He was at a place where he had dealt with the fact that she wasn't his, but it didn't mean he was ready to forget all of the good times they had.
"Are you okay?" she asked "You've been so quiet. Usually you're talking a hundred miles an hour and I can barely keep up."
"Yeah, I'm fine. I'm just a little overwhelmed I guess."
"Overwhelmed? By me?"
"Well, yeah."
Blair reached and selected a dress, she dropped her towel and stepped into it, turning for him to zip it up for her.
"Don't be. I know it's not the most, you know, orthodox situation. Let's just go with it. I've spent so much of my life calculating my choices and I think you have too. Recent events have told me, life's too short." she turned around and looked at Dan "I'm tired. I'm tired of weighing every decision and making everything so final. I just want to live."
"Okay."
"Are you with me? Just living? Not questioning everything?"
"Yes."
"Good. Because last night was… perfect."
"It was."
"Yeah." Blair smiled "Now, Darota is going to be confused when she sees you but just go with it, okay."
"Okay."
Blair and Dan headed down the stairs to the dining room where Darota was putting out breakfast. As expected, she raised an eyebrow when Dan was still there but she didn't skip a beat. She got the jam with four fruits and quickly went back into the kitchen to prepare more toast.
They discussed more of their scheme to get Georgina and decided it should take place at the cotillion that night.
"Ms. Blair, don't forget you have your mother doctor appointment at 11." Darota said, setting the tea kettle on the table "you not want to be late."
"Yes, Darota, I remember." Blair rolled her eyes and looked at Dan whose eyes had turned to question marks
He waited until Darota left for the kitchen before he asked "Her doctor's appointment? Is everything okay?"
"For now… but, no." Blair looked down at her croissant, staring intently
"What's wrong?" he asked tentatively, not wanting to overstep his boundaries, whatever they might be
"She has…." Blair looked up at Dan, her eyes filling "She has cancer."
"Oh God." Dan muttered to himself, he stretched out his hand and instinctively took hers
"Apparently she has for a while but she never told me." She said sarcastically "But, I found out a few months ago when she was sick. Don't tell anyone, not even Chuck knows yet. But it's why she gave me Waldorf Designs."
Dan stared at her empathetically, not knowing what to say. He'd always been sensitive to her pain ever sense he met her. He realized this must have been why he saw the sadness in her eyes the day before.
"Blair, what can I do for you?" he asked
"Nothing. I'm, um, I'm okay I guess. It's just been weird." A tear streaming down her cheek "and hard to keep it from everyone."
"I can't imagine. But you don't have to keep it from everyone."
"Who am I going to talk about it with? Serena and I haven't been that close lately and Chuck has his own problems. And Nate's, well, Nate. I'm not going to tell my minions. And you and I were… well, I didn't know where we were."
"I am always here for you. We were friends before, I am your friend now."
"It's that easy?"
"No thinking, that's what you said earlier. Right?"
"Right."
"Do you want me to go with you to the appointment?"
"No, I think I should on my own."
"Okay. It's an open invitation."
"Thanks Dan." Blair smiled and wiped the tear from her cheek
Dan smiled and looked at his watch.
"Okay, I should get going then so you can go. I'll see you later."
"Okay. "
They both stood up and Blair walked Dan to the elevator. He pressed the button and turned toward her, his eyes lit up. She walked over, stood on her toes, took his shirt in her hands to pull him closer, and gave him a sweet kiss.
"Thank you Dan. For everything."
"I'll see you later, Blair."
The elevator came and he stepped in. The door closed and he was gone.
It was just supposed to be one scheme but he had breakfast with her and had her confidence.
Later that day Dan got dressed for the cotillion. He selected his best suit and a shirt. The shirt he wore for his book party and then again for the party he and Blair never made it to, instead having sex in the elevator. He decided to do something different with his hair, slicking it back.
He got to the party on time, if not a little early, and after making niceties with Serena at coat check he scanned the room for her. He saw her standing across the room, away from the crowd. He walked to the bar and requested two drinks, deciding that would be a good way to break the ice. As he walked toward her he noticed her playing with a necklace with what looked like a ring attached. Keeping his expectations low, he hesitates, but continued walking to her.
"Hi" he said, "I brought you-"
"Oh good. I need a drink. Thank you Dan" she said smiling weakly at him.
"So, have you seen her?"
"Georgina? No, not yet. I did the other thing we talked about so I'm sure she'll be pissed when she gets here."
"Great, great. That should be fun. Uh," he lowered his voice "how did the appointment go?"
Blair sighed and looked at the ring she had been playing with. Dan's eyes followed hers.
"Not great. She needs more chemo," her voice barely a whisper "but they don't know how much it will even help."
"Blair. I'm sorry."
Blair forced a smile and looked up at him, "Thanks."
"If you need anything. Let me know."
"Okay I will."
Blair's eyes shot Dan a warning glare and he looked behind him to see Chuck walking toward him.
"Humphrey." Chuck said, looking him up and down.
"Chuck." He replied with a hint of distain in his voice. Turning to Blair he said "I'll talk to you later."
"Okay."
Dan walked away and back to the bar for a refill. He considered leaving but remembers he has to be there to help when Georgina gets there. Escaping the crowd, he went back to the coat check and sees Serena again. He talks with her for a minute before seeing Chuck walk out. After a few minutes he decided to go back into the main ballroom and bumps into Blair who still seems out of sorts and is fidgeting.
"Is everything alright" Dan asked, almost half heartedly
"Yeah" she replied, looking around the room.
Suddenly, the music changed and Blair looks wistfully at the dance floor where people have partnered off.
Taking a chance, Dan decided to take in the moment, "Would you like to dance?"
"Yeah. Okay."
Dan takes leads her to the dance floor. He puts his arm around her waist and she moves in close and rests her head on his shoulder and his head is resting on her hair breathing her in. For a moment, it feels like they are the only two in the room.
"What was the ring you were playing with" Dan asked quietly
"Oh?"
"The one around your neck?"
"That's uh… something Chuck gave me. It's a promise ring."
"A promise ring?"
"It's silly, I know."
"I didn't say that."
"No, I did."
"So you guys are promised to each other? How is that different from an engagement ring?"
"We're not ready to get married. I'm not ready to get married."
"Why?"
"I just… I want to be sure this time."
Dan is staring into her eyes, trying to remember to approach it as a friend and not be bitter. A twinge of hurt runs through his body but it's a pain that's familiar.
"Okay. What makes you unsure?"
"It's not what. It's who."
"Who?" Dan was honestly taken aback
"I think you know." She said, blinking her doe eyes dramatically
Dan decided not to keep questioning and instead hugged her tighter. She put her head back on his shoulder and they finished dancing. When the song was over he squeezed her tight and looked down into her eyes. His heart sank and he felt a twinge of guilt. The same that he felt this morning. She was not his anymore; no matter how much he wished she was. The longing was something he couldn't quiet shake, even though he wished he could.
The scheme goes on without a hitch and Georgina leaves in a huff. Blair follows, deciding to meet up with Chuck at the Empire. As Serena turned to leave she asked Dan if he's heading home too and he said yes. Things have gotten better between them and so they walk home together. They find themselves sitting outside a small gelato place talking and making plans for another day. Dan knows that he'll never feel for her the way he feels about Blair but he also realizes that Blair isn't his. So making a date with Serena is just to help him move on.
A few days later Dan takes his Vespa out for a ride to the park. Everyone in the city seemed to be buzzing around him but he shakes it off as the city in a flux. When he got to Central Park he saw Serena and photographers who seemed to be chasing her. Confused, he rode over to where she was standing.
"What's going on?"
"Dan, thank goodness. Get me away from here!" Serena exclaimed
"Wow, what a hot sex tape!" one of the photographers said
"Will there be a sequel?!" exclaimed another
The news made his heart sink as he realized the implications of their questions. The sex tape from the Shepard's divorce party… nothing good can come from this. He drove the Vespa away from the crowd and down a few streets to a secluded alleyway. He stopped the bike and turned to Serena.
"Sex tape?" he asked anger rising in his voice
Serena looked down at the ground and then back up at him
"How the hell did Gossip Girl get that video?! I thought you deleted it?"
"I don't know."
"Did you delete it?" Dan was furious
"Someone must have sent it from my phone."
"Who?!"
"I don't know. Dan, I'm sorry. I was kinda out of it this summer."
"Serena, what the hell?"
"I don't know. Just, just take me home. I'll figure it out from there."
Dan got back on the Vespa and drove to the Van Der Woodsen's, stopping only in front to let her off. He continued on looking around for a place to buy Blair a gift. Maybe she hadn't seen the video, he hoped. Plus, her mother had another appointment and he wanted to see how it had gone.
While inside the chocolate shop Blair stood outside peering in. Her heart racing, she'd just seen the blast. Tentatively, she walked inside just as Dan was checking out.
"Blair- what? What are you doing here?"
"I saw you on the spotted map."
"On. Oh, on Gossip Girl?"
"Yes," she said flatly
Oh crap, he thought. She must have seen the video. However, Blair was nice enough to wait until they were outside before she let him have it.
"What were you thinking?!" she exclaimed, angrily, poking at his chest
Dan stepped back and hesitated.
"I wasn't!"
"Obviously!"
"I waited for you to meet me at the Shepard's party and you never showed up! You didn't even tell me anything you just went groveling back to Chuck! Again!"
"You had sex with Serena when we were still in a relationship!"
"You were back with Chuck! She showed me you going to meet him a the Empire!"
"So our relationship meant so little to you that you slept with Serena on the bar at a party?!"
"So our relationship meant so little to you that you didn't even admit to me that you were going to grovel at Chuck's feet again?!"
"Humphrey you are ridiculous."
"I am ridiculous?! You used me and then left me."
"I tried to explain!"
"Yes, after the fact! By email!"
"You slept with my best friend when you supposedly loved me."
"Well, you didn't love me."
"I can't even. I can't even look at you right now."
"Why do you even care?!" Dan found himself shouting, he really wanted to know
"I thought. I thought I meant more to you."
"More to me? Blair, you mean everything to me!" Dan momentarily berated himself for saying "mean" when he should have said "meant," even thought he said the truth
"Obviously not or you wouldn't have slept with her." She said, distain on her tongue
"I can't ration away what I did. It was wrong. But you were wrong too! Admit that you used me."
"I can't deal with this right now."
"Fine. I need to be going anyway."
"Where?!"
"To see Serena."
"Great. I hope you're happy together." She said spitefully
"I hope you and Chuck are as well." He said returning the spite
Dan turned and walked away. He crossed the street and tossed the box of chocolates in the trash on the other side. Blair's phone rang and she took the call and quietly walked in the other direction.
It was just supposed to be one scheme. Yet here he was feeling as in love and lost as ever.