AN: I own nothing except the storyline and characters not seen in the show!

Chapter 1

"Uh, Serena, whose bags are those? If they're Jenny's, tell her that I love her but she just can't live on our couch for the next three months or I will be forced to kill her." Dan called into his penthouse to his wife of six years.

Serena and Dan, to no one's surprise, had married straight out of high school in a wedding that rivaled Lily van der Woodsen's to Bart Bass. It was elegant and formal and everything that Dan and Serena hated, but they did it to make Lily happy. It didn't matter to them, as long as they were together.

"Sorry to disappoint C.P., but it's me." Blair Waldorf called out.

"Aunt Blair?" A young voice shouted; more specifically, the voice of Serena and Dan's five year old son Ryan.

"Ryan?" Blair returned in the same voice of anticipation and joy.

Ryan ran into the living room, where Blair and Serena had previously been situated; Blair and been drowning her sorrows in scotch while Serena tried to understand what she was saying. They had been there for the last four hours and very little progress had been made.

"I missed you!" Ryan shouted as he ran into Blair's arms, nearly knocking her down, and engulfing her in the biggest hug his five year old arms would allow.

"Oh, sweetie, I missed you too." Blair said, hugging him back.

Back in the hallway near the front door, Dan, Nate, and Chuck were at a loss for words. None of them had seen Blair in over a year, since she had jetted to Europe with her latest billionaire boyfriend. Dan was pleased that she was here, he had grown to like her their senior year of high school and he appreciated the fact that she doted on his son like no one else.

Nate and Chuck were not as thrilled. Blair was the one thing that had threatened their friendship and while neither would admit it, they had been relieved when she moved away. It allowed them the opportunity to mend bridges and attempt to return to their pre-Blair glory.

Dan walked into the living room and Nate and Chuck followed. Blair walked over, Ryan still in her arms, and hugged each of the men before her.

"It's so good to see you all." She said brightly. Dan smiled and Nate and Chuck just nodded.

"To what do we owe this pleasure?" Dan began. "And, it appears that your hand is quite lighter."

"I've decided to come home; I can't be away from New York for too long." Blair said, not answering Dan's second comment.

"And Pierre?" Dan asked as Serena shot him a warning glare which Blair caught.

"It's okay Serena. Pierre and I are no longer together. Who had bets on a year and two months?" Blair said sarcastically.

"Blair." Serena said.

"No, it's fine S. I'm not bitter; I've come to accept it." Blair said seriously, ruffling Ryan's hair in the process. "You look more handsome every time I see you. Are you batting away the gold diggers yet?"

"No." Ryan said shyly.

"Accept what?" Dan asked and again received a stern look.

"Accept that I'm going to be alone. I mean, let's face it; I'm not getting any younger. Each day, everything starts to sag more and more and no matter what new procedures are out there, I'll never be the same. And you know this is my third failed engagement. How many times do you think one person will get proposed to? Three, I'm already way over my expected quota as it is. No, I'm done. I won't get another shot. Damn, I really should've stayed with Steven." Blair explained.

"Blair, that's not true." Serena tried to comfort. "There are plenty of men that would kill to be with you."

"Yes, be with me, not marry me. But its okay, I'll get a cat or something." Blair said in a resigned voice.

"What about me?" Ryan asked sadly.

"Oh my goodness, I almost forgot our plan. No, I won't be alone after all." Blair said and put her God son down.

"Plan?" Dan asked curiously.

"Yeah, when I'm 18 and my trust fund kicks in, Aunt Blair and me will go to Las Vegas and elope and move to Europe." Ryan said, looking up at Blair to confirm. She nodded her head in agreement.

"Nice." Dan said looking at Blair and shaking his head. She just laughed.

"So did you get me anything?" Ryan asked Blair.

"Of course." Blair responded ignoring Serena's disapproving looks. "Go get me the bag with the big C's on it, okay?"

"You and Chuck are going to spoil him if you don't stop it." Serena chided.

"What can I say; I just want to make sure my nephew is well cared for. I know how Brooklyn can be cheap." Chuck said with a smirk.

"So true." Blair said with a grin towards Dan.

"Here." Ryan thrust the bag into Blair's hands.

Blair fussed about for a moment, rearranging the items within until she pulled out a wrapped box. She handed it over and within moments the paper was torn off. It was a model jet, one of a kind. Ryan loved these types of toys and this would be the centerpiece of his collection.

"Thank you! You're the best!" He shouted and gave her a hug.

"And don't you forget it." She said and beamed at him. He really was the perfect kid.

"What about me?" Chuck asked, pretending to be hurt.

"And me?" Nate chimed in with the same hurt tone.

"Sorry." Ryan mumbled as he focused on opening his box. He soon ran into his room to play with his new favorite toy.

"So where's the ring?" Serena asked, suddenly curious as she hadn't seen it apart from Blair in months.

"I gave it back to him. You can't keep an engagement ring once you're not engaged. Jewelry, yes. Priceless family engagement rings, no." Blair explained.

"Too bad, it was perfect." Serena said wistfully.

"Don't I know it?" Blair responded. "I am such an idiot. I should've stayed with him."

"But you didn't love him." Serena said.

"Well your mother never loved any of her husbands and it never stopped her from marrying any of them. The thing you have to understand, Serena, is that most people never find their true love. You and Dan are the one exception. Apparently, my true love is either non-existent or already taken so I just have to settle for rich, hot, cheating French assholes." Blair said and let out a sigh. "Maybe I'll call him."

"Absolutely not." Serena shouted.

"Whatever." Blair sighed. "So…what's new with you two?" Blair directed towards Nate and Chuck. The both looked at each other for a moment and then at Blair.

"Well, I'm, uh, engaged." Chuck stuttered.

Blair looked shocked for a moment but then regained herself. She walked over and gave him a hug which he unsurely returned.

"Congratulations. Don't mind me saying this, but I never thought I would see the day." Blair said and laughed.

"Tell me about it." Chuck said with an awkward chuckle.

"But good for you." Blair said seriously. "I'm glad to see that you're happy and doing well. And what about you?" Blair asked Nate.

"Me? I'm single. I just got out of a long term relationship so I'm enjoying the life of a bachelor." Nate said with a grin.

"Interesting. How's work?" She asked.

And for the next couple of hours, the five happily chatted about life and caught up on all that they had missed since they last spoke. Finally, Blair excused herself to get some sleep; jet lag had caught up with her. Nate and Chuck left and Serena, Dan, and Ryan had a quiet family dinner.

Early the next morning, 9:15 to be exact, Blair was shuffling about the Humphrey's kitchen, trying and failing to brew coffee while Ryan watched happily.

"I think this thing is broken." Blair complained to her God son, referring to the coffee maker.

"Daddy used it yesterday." Ryan said with a giggle.

"Yes, and maybe he broke it yesterday." Blair said and picked Ryan up. "What do you say I take you down to the restaurant downstairs and we get breakfast there? Sound good?"

"Yay!" Ryan let out.

"Okay, let me write Mommy and Daddy a note so they don't get mad." Blair said and did just that. Then she found her bag, took Ryan's hand and went to the elevator.

"Chuck!" Blair said in surprise once she and Ryan arrived at the restaurant. "Long time no see."

"Hey." Chuck said, giving Blair a hug and Ryan a high-five. "Ryan, what's good?"

"Aunt Blair couldn't work the coffee machine so we're having breakfast here." Ryan offered.

"I'm not surprised." Chuck laughed. Blair gave his arm a playful slap.

"What is that supposed to mean?" She said, pretending to be offended.

"Nothing. What about you two join me as a way to make it up to you?" Chuck asked Blair.

"Yes! Yes!" Ryan yelled.

"Are you sure? We don't want to be in your way." Blair said.

"I'm positive. C'mon." He said and led them to his personal table.

"What are you up to today?" Chuck asked when they sat down.

"Oh nothing too crazy, maybe the zoo or park." Blair said as she looked over the menu.

"Zoo?" Chuck asked in a disbelieving voice.

"We're leaning towards the park." Blair said with a smile and closed her menu.

"Hello Mr. Bass. What can I get for you all?" The pretty blonde waitress asked as she glided towards the table. Chuck pointed to Blair.

"Umm, I would love a cup of coffee and is it possible to get whole wheat waffles?" Blair asked politely.

"I'm afraid we don't make whole wheat waffles." The waitress responded.

"Okay, then I will have the fruit salad." Blair responded.

"No you won't." Chuck said. "Kelly, tell Alfonzo that he will prepare whole wheat waffles precisely to Miss Waldorf's specifications. Okay?"

"It's fine." Blair tried but Chuck wouldn't hear it.

"Ryan and I will have our usual and I'll have a cup of coffee as well." Chuck said and dismissed the waitress with a wave.

"Ryan, here is a perfect lesson for you. When you're out with a pretty lady, you do whatever it takes to make sure she's happy." Chuck said to Ryan who nodded seriously.

"Thank you. That was completely unnecessary, though." Blair said and blushed.

"Are you kidding, I've seen you when you don't get what you want. That was primarily for Ryan's safety." Chuck said with a smirk.

"Ha-ha, I've forgotten how funny you are." Blair said but she was still smiling.

Breakfast went smoothly after that. The food was delicious, even if it was just standard breakfast food. Chuck and Blair were talking nonchalantly while Ryan watched when a petite brunette walked up to the table.

"Hey, baby, what are you doing here?" The brunette said, pulling Chuck and Blair out of their conversation.

"Hi Jo, I was just catching up with an old friend. Joanna this is Blair. Blair this is Joanna, my fiancée." Chuck said trying to appear as if this wasn't completely awkward for him.

"Hello, Blair Waldorf. It's a pleasure to meet you. I've heard such nice things about you." Blair said as she thrust out her hand and plastered her best society smile on her face.

"Joanna Martin, it's nice to meet you too. I'm sorry but I haven't heard much about you." Joanna said, looking at Chuck suspiciously.

"I'm not surprised; I've been in France for the past year." Blair said brightly. "Well, let us get out of your way." Blair said and gathered her belongings. She attempted to pull out her wallet but Chuck shook his head.

"It was nice to meet you. Thanks for breakfast Chuck." Blair said and pulled Ryan after her.

"Mommy, Daddy, you won't believe what happened today!" Ryan exclaimed as he ran into his penthouse.

Serena, Dan, and Chuck sat in the living room, sipping drinks and chatting.

"Where have you been? And where is Blair? I can't believe she had you out all day. I'm going to kill her." Serena said seriously.

"Uh, Blair is at the bar for the time being." Nate said, trailing in behind Ryan in a jogging suit.

"Why? What happened?" Serena asked, suddenly nervous.

"Aunt Blair is having a meltdown." Ryan said with a smile.

"A meltdown? What does that mean?" Serena asked, still panicked.

"Trust me when I say this, you're going to want to hear it from her." Nate said with a grin. He walked over to the bar and poured himself some whiskey.

Just then, the door creaked open and a moment later was slammed shut. Blair walked into the living room, where she shot Nate a dirty look and plopped herself down on a couch. She was looking quite disheveled. She was wearing shoes that looked as if they had been bought from one of the street vendors and a shirt that said 'I Love NY' over her teal Dolce and Gabana dress.

"I don't want to talk about it." She said and put her head down between her legs.

"Blair, what happened?" Serena asked, ignoring Blair's previous statement and walking over to her.

Blair opened her bag and pulled out a pair of Manolo Blahniks. She handed them to Serena and shook her head.

"I thought these were heels, not flats." Serena said.

"They were." Blair mumbled, both of her hands covering her face.

Serena, Chuck, and Dan tried to suppress giggles but Nate let out a chuckle. Blair glared at him.

"It's not funny. Those shoes cost a fortune. They were a gift from my father." Blair said, and rested her head on Serena's shoulder.

"I hate to say this, but the shoes are probably the least of your problems." Nate said with a grin.

"Don't you smile your little puppy-dog smile at me Nathanial. I am extremely mad at you right now." Blair said, shooting Nate yet another strong glare.

"Why are you mad at me? Am I the one who threw up on you? No. It's him you should be mad at, if anyone." Nate said, gesturing towards Ryan.

"I didn't mean to." Ryan said apologetically.

"I know you didn't, sweetie. I'm not mad at you." Blair said. "He's five, he doesn't know his limit. You should have known better than to buy him two sticks of cotton candy." Blair said angrily to Nate.

"You threw up on Blair?" Dan asked with a grin.

"Yes he did." Blair sighed.

"Wait, I'm confused. I thought it was going to be just you and Ryan today." Serena said to Blair.

"It was but then Aunt Blair's shoes broke and Uncle Nate caught her like a prince in a fairytale." Ryan said in awe.

"Actually, it wasn't like a fairytale because, and correct me if I'm wrong, but in a fairytale, the prince does not almost drop the princess and he most certainly does not laugh when she gets thrown up on." Blair huffed.

"Now, if you'll excuse me, I need to go shower and throw out my dress." Blair said and walked into the guest room.

"Nate, what happened?" Serena asked after she was sure Blair was gone.

"I was taking a jog through the park and then I see someone who looks like Blair with a kid who looks like Ryan, but I was sure it wasn't her. But then, as I'm right next to them, I see her shoe get caught in a crack in the pavement and the heel snapped. So I put my arms out to catch her, and I almost dropped her. I realized then that it was Blair and Ryan and I bought her a pair of shoes from one of those stores on the street and then I bought Ryan some cotton candy. You know the rest." Nate said with a smile and wink towards Ryan.

"It was really funny. Aunt Blair started crying when I threw up on her." Ryan said with a mischievous smirk.

"Ryan, that isn't nice." Dan said sternly. However, this did not have its desired effect as Dan was smirking as well.

"Ryan, let's go get you ready for Grandma's." Serena said and led Ryan to his room.

"So was she really crying?" Dan asked incredulously when Serena and Ryan were gone.

"Oh, she was hysterical." Nate laughed. "I could tell she was trying to act calm so Ryan wouldn't feel bad but she couldn't control herself."

"What I would have paid to see that." Chuck said with a giant smirk.

"Oh, so guess what happened at breakfast. I ran into Blair and Ryan downstairs and we ate together." Chuck began.

"How did that go?" Nate asked.

"Actually, much better than I thought it ever would. Anyway, at the end, Joanna walked in." Chuck paused for dramatic effect.

"And…" Dan said.

"And Blair was really nice to her. I think she likes her. Now as for Joanna, she was not too pleased. It took a lot of convincing that nothing was going on between Blair and me." Chuck said.

"Was Blair real-nice or that fake nice that she was whenever someone she secretly hated was around?" Nate asked curiously.

"I'm not sure. I think she was genuinely nice but I can't read her like I used to." Chuck responded, thinking back to the morning. "Why wouldn't she like Joanna, anyway?"

"You're kidding, right?" Dan asked patronizingly. "Even I can tell you that one. Blair doesn't like competition."

"But it's not like we were ever together. I mean I would understand if this were Nate we were talking about but me?" Chuck said in disbelief.

"I have to agree with Dan about this. Blair is funny about these things." Nate said.

"Well, I have the perfect way to see. Why don't we invite Blair to dinner with us? Then you can all see how Blair acts around her." Chuck said with a smirk and the boys nodded. Dan looked worried and Nate just plain excited. Chuck, well he didn't know what to make of this.

Dinner was a horrible idea. Too bad Chuck had realized this a little too late. Blair looked beyond stunning and Chuck couldn't keep his eyes off of her which could be problematic with his fiancée sitting right next to him.

"Blair, you look beautiful." Nate said as he pulled out her chair for her. Dan and Chuck did the same for their respective dates.

"Thank you." Blair said shyly and blushed. "You look nice too."

"I do what I can." Nate said smugly.

"You're such an ass." Blair shot back. Nate just smiled.

The cocktail section of the night went along quite nicely, despite the constant glares Joanna was sending Chuck. He just shrugged his shoulders and mouthed "what?" but she shook her head in frustration.

Just as Blair was on her third martini, the waiter brought over a bright blue drink for her.

"Umm, I'm sorry, I didn't order this." Blair said in confusion.

"It's from the gentleman over there." The waiter said, indicating with his hand who had sent the drink. As soon as the waiter said this, the man got up and started walking towards the table.

"Put your arm around me." Blair ordered Nate through clenched teeth.

"Why?" Nate asked.

"Just do it. And you're my boyfriend." She mumbled.

The guy walked over to the table, straight towards Blair.

"Hello there, pretty lady." He said drunkenly.

"Are you trying to hit on my girlfriend?" Nate demanded angrily.

The man shook his head no. Nate was a built guy and could be intimidating if he tried. The guy apologized and quickly walked away.

"Just like old times, right?" Nate laughed. Blair pushed his arm off her shoulder.

"I'm still mad at you." Blair said.

"Yup, exactly like old times." Serena said and everyone cracked up, except for Joanna, who didn't understand.

"C'mon, you know you don't want to be mad at me. I have a puppy-dog smile." Nate said and grinned.

"Just because you have a nice smile, and bright blue eyes, and are good in bed, and have a nice body doesn't mean I'll forgive you at the drop of a hat." Blair huffed. Everyone paused in shock.

"You said I was good in bed." Nate finally said with a smirk.

"No I didn't." Blair said as her face reddened in embarrassment.

"Oh, yes you did." Nate said.

"Oh, God, kill me." Blair said and buried her face in her hands.

"Don't worry, you were good too." Nate said smugly and put a suggestive arm around her.

"I know." Blair said angrily and again pushed his arm off her shoulder. Nate and Dan laughed, while Chuck forced an awkward chuckle. This conversation was getting into dangerous territory.

"Anyway…does anyone else think that it smells like sex in here?" Serena asked in an innocent voice.

"I'm going to kill you." Blair muttered and then downed the blue drink in two gulps.

Dinner went by quickly after that and a lot more pleasant for Chuck. Apparently, Joanna had taken Blair's confession to mean that she was still into Nate and therefore not interested in Chuck. Joanna warmed up to Blair and Blair in turn was as sweet as she could possibly be. More impressive, it seemed she was being genuine.

After dinner, Dan and Serena excused themselves, claiming they had to pick up Ryan from Lily's house. Nate, Blair, Chuck, and Joanna decided to get dessert and after-dinner drinks at a bar across the street from the restaurant they were in.

"So, do you think that you guys will ever get back together?" Joanna asked, looking from Nate to Blair.

"No!" They both shouted simultaneously.

"Why not? You two seem like you would be the perfect couple." Joanna encouraged. Blair took a large gulp of her drink.

"Let's just say, we had a messy breakup." Nate said and took a drink himself.

"What happened, if you don't mind me asking? I feel so out of the loop." Joanna said. Blair took another swig.

"She slept with my best friend." Nate said; though it lacked the bitterness it once held. Time and the several drinks he had had helped that.

"Only because you slept with mine first." Blair slurred a little. She was way ahead of everyone in the alcohol department.

"Call it even?" Nate asked suddenly.

"Okay!" Blair said and gave him a high-five and they both grinned.

Chuck's face was beet-red and he was trying not to catch anyone's eye. Joanna, however, had not had anything to drink tonight and was as sharp as a tack.

"Best friend?" She asked to Nate.

"Uh hu. That guy over there." Nate said obliviously and pointed to Chuck whose face turned a brilliant shade of magenta.

"I see." Joanna said darkly and remained silent the rest of the evening.

Some quotes in the story above were borrowed from other works, so I've cited them here for anyone who's interested.

"And don't you forget it." – Closer (Movie)

"Hello there, pretty lady." – She's The Man (Movie)

"You said I was good in bed."

"No I didn't."

"Oh, yes you did."

"Oh, God, kill me." – One Tree Hill (TV Show)

"…it smells like sex in here…" – One Tree Hill (TV Show)