Chapter 2: Family Affair

6 months…

Milo squirmed as he tried to roll off the diaper table whilst Dan was attempting to change him and put him into his clothes that didn't have spit up stains (and if we're being completely honest, those outfits were few and far between). Dan was worried for that child's safety. He'd turn around for half a second to grab a baby wipe and the next thing you know, Milo was headed for a soft rug with a hard landing.

"You know, I don't know why you have to make this so hard for Daddy, all he's trying to do is make you look nice for brunch with Gramma and Grampa," Dan sighed as he finished wrapping the diaper around his child and putting some little khakis over Milo's kicking legs. Dan propped him up on his feet and made Milo do a little dance while making a big smile and humming Train's "Hey, Soul Sister". Milo broke into a fit of giggles, which caused Dan to laugh too as he scooped Milo into his arms and showered him with kisses. Dan's heart filled with joy. He could see the wonder in his eyes and as much as he loved his family, he didn't want the Upper East Side to ruin this child before he could even walk.

Dan carried Milo out into the living room and placed him in his Pack and Play, so Dan could finish getting ready. He put his button up shirt on, buttoned it, and was just rolling up the sleeves when he heard the loft door slide open. Serena walked in, tall and gorgeous as ever.

"Morning! I was just making sure everyone was up and ready for another Sunday brunch," Serena smiled, walking over to Milo and picking him up.

"We're always up by 6:17, on the dot," Dan blurted, disappearing into the nursery.

"We've just been concerned, Dan. You solemn miss Sunday brunch with Mom and Rufus, and it's been a few weeks now,"

"Like you haven't missed any? This is the first time in a while you've made it to every Sunday in one month," Dan reappeared with a rusty red and charcoal grey diaper bag. He grabbed Milo's favorite teething toy from the freezer (a ring with different rubber textures) and his pacifier/stuffy/animal combo.

"This is not a time to play 'who has it better/worse, I was just coming over to see my stepbrother and nephew, before the grandparents start gushing over how big he's getting. I wasn't too happy with the blast a few months ago either, you know,"

"You're right, I'm just stressed out. Like my schedule is working out perfectly, between school, working, and spending time with Milo, but I just still have a huge weight on my shoulders,"

"Is it because they called off Georgina's search?" Serena questioned cautiously. Dan sighed, while taking Milo and strapping him into the stroller. He hooked the diaper bag around the stroller handle.

"Yeah…that's been hitting me hard a lot. But not because of me, I never loved her; she was absolutely crazy. But for Milo's sake. Soon, he'll be walking and talking and I'm trying to figure out how to explain his existence and how it coincides with my life,"

"Dan, Milo hasn't even started walking yet. He's still got another 6 months before he has his first birthday. You don't have to give every single detail right off the back; just feed it to him little by little as he gets older," Serena explained as they walked out of the loft and headed for the subway. Her heart broke as she saw how sad Dan was. He covered it up well with his love for Milo, but deep inside, you could tell he was torn apart. Serena vowed that the next time she saw Georgina, she'd make her understand how much trouble Dan went through to make that baby's life the best life he could ever have.


Taking the train with a stroller was always a pain, but with Serena's help, it was more manageable than when Dan had to go to school. They arrived in the UES around eleven and made their way to the loft. Jenny had come back this weekend from Hudson, and Dan was surprisingly excited to see her; he just really hoped Serena and Jenny wouldn't cause a scene. After Jenny had tried to ruin Serena's life at the masquerade, Dan was trying to Jenny some space. The Upper East Side has rocked her world and he hated that he couldn't do anything to save her before Blair gotten her hands on her.

The trio took the elevator up to the loft and made their way in. Rufus was finishing up his famous waffles in the kitchen while Lily was finishing setting the table. Their faces lit up when they saw Milo for the first time in a few weeks.

"Oh, there's our favorite boys!" Lily squealed, unstrapping Milo from the stroller while he chewed on his own fingers.

"And one of our favorite girls of course," Rufus added, pulling Serena into a hug. Dan removed the diaper bag from the stroller and folded it up. He put it in the open coat closet and brought the diaper bag into the living room, where everyone had settled.

"Uh, hey, where's Jenny?" Dan questioned, setting the bag down next to the coffee table.

"She's in her room, gathering some extra clothes to bring home. It's a little colder in Hudson than she remembered," Rufus explained, taking Milo gingerly from Lily, "I'm sure she'd love to see her nephew." Dan smiled and picked him up, then brought him into Jenny's room. He stopped in the doorway and just watched his sister. She seemed way less tense then when she had been in New York City.

"Special Delivery," Dan smirked, while rapping quietly on the door frame. Jenny turned around and he face broke into the biggest smile.

"Dan! And Milo!" Jenny exclaimed, jogging over to the pair and enveloping them into a giant hug, "How is Milo, and more importantly, how are you?"

"Milo is hitting every milestone just fine, soon he'll be crawling everywhere and I'll have to get six extra sets of eyes around my head. Although, he's a cranky teether. Like I know that baby's hated teething because it hurts so badly, but he's miserable when a new tooth comes in,"

"Aww poor little bear," Jenny cooed whilst brushing her finger across his cheek, "And you?"

"I'm hanging in there, beyond thankful that Milo is a relatively easy baby to take care of. The whole Georgina deal has…broken me into pieces, but I'll be okay. I have no choice but to be. My life has started revolving around bettering mine and Milo's lives, and that's the best thing I can do for the both of us,"

"I'm so proud of you, Dan," Jenny pulled him into a hug, "I always have been." They made their way back to the dining room so brunch could begin. Dan strapped Milo into his high chair, and had just sat down when Milo started to whimper. His cheeks were turning red and tears welled in his eyes.

"Uh oh, what's wrong little bear?" Serena tried to appease him with a waffle, but he batted it away and burst into tears.

"He's just got another tooth or two coming in, nothing new." Dan jumped up and grabbed the bumpy teething ring from the diaper bag. He sat back down and positioned the ring in Milo's mouth, where Milo gripped it with his little hands and began to gum it. Dan pulled out a pocket pack of tissues and used one to wipe Milo's leftover tears and then his dribbling, snotty nose. Everyone stared at him in awe.

"What?" Dan questioned, as he got up to throw the tissue away and wash his hands.

"We've just…never seen you really parenting," Lily sipped on her champagne.

"You've just been so busy we haven't seen you much. And that was just…I've never seen such a natural with a baby, especially at your age," Rufus patted Dan on the back.

"I can't take all the credit, those baby books are usually pretty helpful. And I mean, I'm twenty, not the most preferable age to be a father, but you've got to do what you've got to do," Dan brushed Milo's hair out of his face and switched the teething ring out for a bowl of apple sauce. He began spoon feeding Milo, whose favorite activity at this age was eating and causing trouble.

"I'm so sad that I have to go back to Hudson and miss seeing Daddy Dan," Jenny picked on him, fake pouting and all.

"It's almost twelve thirty right? And your train leaves at one thirty, so why don't I treat you to coffee and drop you off at Grand Central," Dan offered.

"I would love that!" Jenny exclaimed, the young adults' phone's lit up with another Gossip Girl blast.

Spotted: Little J at a weekend hurrah with her family in the Upper East Side. Aunt Jenny is going to have hell to pay when Queen B finds her. A game of hide and go see for J it is, so she better start running. XOXO

"C'mon!" Jenny slammed her fists on the table as she got up and made her way to her room to get her suitcase and backpack.

"What's going on?" Rufus stood up, and started cleaning off the table.

"Gossip Girl gave away that Jenny is here, and now Blair will following us on the GG spotted map," Dan explained, unstrapping Milo from the high chair and strapping him into the stroller. Milo was given his teething toy back, and he resumed gumming it.

"Blair was going to completely destroy her, but Jenny left before she got a chance to," Serena added while she grabbed their jackets and tossed them to their owners.

"Are you sure you want to take little bear with you?" Lily questioned, clasping her hands nervously. Jenny hugged her dad and step mom and made her way to the elevators

"Oh yeah, he's gonna help us get J to Grand Central without a hassle," Dan yelled as the three siblings stepped into the elevator and began their game of tag with Blair.


"So what's you bright idea, Dan?" Jenny crossed her arms over her chest.

"Serena and I are going to walk there, so you two need to switch shoes. Blair knows Serena doesn't wear flats,"

"Umm how do you know I don't wear flats?" Serena turned to face Dan.

"Because I haven't seen you in flats over then when you wear slippers, now just switch your shoes," Dan gave her a look. The two girls sat on the benches in the foyer of the apartment building where the loft was.

"Jenny, you're gonna take the 6 and the 4 and it'll take you right into Grand Central,"

"Doesn't Blair have a driver though?" Jenny stood up, now three inches taller.

"Yes, but she wouldn't be caught dead in the subway system. She doesn't even like getting into certain taxis without Dorota cleaning the seats first," Serena stood up, now three inches shorter. From behind, they were identical, which would throw Blair completely off her track.

"Ready to go?" Dan started pushing Milo towards the door. The two girls followed in tow, and when they got out the door, the mission was on. Dan and Serena walked Jenny to the entrance of the 6 train, then followed the route Jenny was, but above ground and on the sidewalks. They had to walk fast to keep up with the trains, but Milo thought all the bumps were hysterical. Dan smiled at Milo's giggling, but that smile quickly dropped when Milo's giggles turned into horrific screaming with tears. Dan and Serena stopped walking and moved the stroller to the inside of the sidewalk.

"Hey hey hey, what's wrong little bear?" Dan crouched down to look at his son. He stuck his finger in Milo's mouth and felt around gently.

"Dan, what are doing?" Serena crossed her arms, trying to stay warm.

"Trying to see if he has a tooth coming in, which he does," Dan made his way to the back of the stroller and rifled through the diaper bag. He pulled out a plastic baggy of frozen grapes. He stuck one in Milo's hands and Milo went all in.

"What about the teething ring?"

"Oh, it melted. I would have brought another one, but I wasn't expecting to run around Manhattan. I took some frozen grapes from brunch just in case he got fussy, and they're also his favorite snack," he answered, putting the plastic baggy in the cup holder for when Milo needed a refill.

"Dan, you're incredible!" Serena exclaimed.

"Nope, I'm just a dad," Dan smiled.

"Humphreys!" the pair heard Blair yell from a block away. Dan turned around to see her walking with revenge in her eyes and her Jimmy Choos.

"Go!" Dan turned to Serena and they two started fast walking. They could feel Blair catching up to them, but they were still moving fast. There was only one more block to Grand Central when Blair grabbed Serena's shoulder. The two stopped dead in their tracks.

"Jenny you are so-Serena?!" Blair frowned and pouted. Dan unstrapped Milo and picked him up, because he was starting to squirm and get restless from sitting all day.

"Sorry Blair, I guess we were just too quick for you," Dan stepped toward.

"Where is she?" Blair demanded.

"On her way back to Hudson, she was just visiting. She already feels bad for what happened, and everyone has forgiven her. Why can't you?" Serena rolled her eyes.

"Because she hurt you. And I hate seeing you hurt. You're my best frie-hey what is the droll monster doing," Blair exclaimed as Milo leaned in and grabbed the pearls around Bair's neck and began to suck on them.

"He's teething and loves bumpy things to suck and chew on, since his baby teeth are hurting him," Dan laughed, trying to pry his growling son away.

"Ugh, he can have them. They're all slobbery now." She took them off and Milo leaned back to Dan, expensive pearls and all, "You win this time, Humphrey. Tell Little J to stay away, got it?"

"Of course, Blair," Dan mumbled as they started walking away from the Queen.


They arrived within record time after their detour to grab some lattes to go, and met Jenny near her train.

"Thank you, thank you, thank you!" Jenny smiled as she hugged Dan and Milo tight, "And thank you too," she hugged Serena and handed her shoes back.

"Anything for you, little sis," Dan handed her a latte, "Don't give mom too much trouble, alright?"

"I won't," she kissed him on the cheek and he returned the gesture. He smiled as she got on her train and waved goodbye. Dan and Serena waved back, wondering when Blair would give up the fight.