A/N: Of course I do not own any of the characters. This is just my take of what happened between the cameras and will continue to past where the show took us. Enjoy!
Jenny was woken up early by knocking on her door. "I swear Blair never sleeps" she whined as she got up to answer it.
"Good morning J!" she said as she walked through the door followed by Dorota carrying a tray of breakfast and sat down on the edge of the bed already perfectly dressed for the day.
"Blair it's not even 7 o'clock yet. How are you ready and this peppy?" Jenny questioned as she crawled back under the covers.
"Because it is the day of my best friends Bachelorette party and everything has to go perfectly of course. Eat up and be downstairs ready to go in an hour please. It's really nice to have you back J we've all missed you and although you're doing great with our European branches I want you back in the city with me and have some convincing to do!" Blair said in a tone that scared Jenny a little as though she barely had a choice.
"We will have to see how these next few days go Blair but so far it has been nice to be back around everyone. It has certainly been too long since I have visited to say the least. I will be ready in less than an hour. See you soon!" she said as Blair walked back out the door to let Jenny get ready for the busy day.
Jenny sighed. Maybe what Eric was saying last night would be easier than she thought. If there was actually a mutual spark between her and Nate like she had dreamed of for years it sounded like Blair would be more than happy to have her come back and work in the New York office. But if this failed and everyone was wrong that he had feelings for her then she was certainly going back to London and not returning out of the sheer embarrassment of being wrong. As she showered she thought over and over again how she could possibly approach him. They had always been friends when she lived here. He was so easy to talk to and never judged her crazy, but that had been so long ago. Was he still the same person or had he changed? Would he still care about her? What was she going to say to him after so long? She settled on approaching him like an old friend. She was going to try and not come off as a love struck girl that she currently felt like. Then she laughed out loud. Since when did guys make her so nervous that she needed to plan out a conversation days in advance? This never happened with anyone. The men always seemed to be nervous to approach her. She knew she was an attractive woman and the power of her career added to her appeal to many men but Nate was different. Nate had always been different and he was turning her brain to mush.
As she was doing her make up she found herself asking what he would like her to look like. She knew he preferred the more natural look or at least had the last times they had interacted so that was what she went with today just in case she was to see him since she did not really know what Blair had planned for all day. She put on a beautiful royal blue dress that she had designed herself with Nate in mind because it was his favorite color and she knew he would be seeing pictures of them today if not in person. Jenny looked in the mirror and decided she was worthy and headed downstairs.
When Jenny came down the stairs Serena was sitting on one of the couches and Blair was bustling around doing God knows what. "Do you have any idea what the plans for today are?" Serena asked Jenny.
"Nope I was hoping you did." Jenny laughed knowing everyone had been left in the dark, which was fairly normal for one of Blair's plans. When Blair stopped long enough to realize Jenny was ready she told them just one more minute and they would be ready to go. Dorota ushered them out the door and towards the waiting limo. Blair followed behind and they were off. Inside the limo were mimosas which surprised Jenny for a moment considering how early it was but then she remembered it was not an event on the Upper East Side if there was no alcohol included. Blair finally clued them in that they were heading to an exclusive spa to begin their day. Massages, manicures and pedicures, facials and Serena even did one of those seaweed wraps that Jenny thought was a little too weird for her. It was such a relaxing morning that Jenny was dreading leaving and continuing on their adventure. She wanted Elsa to massage her for the rest of the day. Her life in London was always so hectic she never got the chance to be utterly relaxed like this. She decided she needed to set aside a little time for herself no matter where she ended up living (hopefully in Nate's penthouse) and just thinking about that made her blush.
Far too soon their time at the spa ended and Blair said they were continuing their day at Le Cirque. Jenny had never heard of it but Blair said it had a ridiculous waiting list for tables and had some of the best French cuisine in the city.
"Mrs. Bass we are so glad to have you here today I will show you to your private table in the back" Jenny had to hold back a laugh as the host lead the women to their table. Of course these people knew Blair by name. There were definitely some aspects that had not changed and maybe even got worse since she left. All the eyes were on them as they were lead through the restaurant. Jenny assumed most of them were on Serena. They always were. She just radiated beauty and happiness and Jenny sometimes envied her confidence. Then if they were not looking at Serena, Blair had captured their attention because everyone in the city and probably far beyond the island knew she was one of the most powerful women in the world. Then there was Jenny. Jenny was convinced no one would notice her at all today around these two. She would just be the awkward one in the back that no one bothered to even ask who she was. But Jenny was wrong. She always underestimated her beauty. She was different than the other two women. No less beautiful than them and was truly well accomplished but she gave off a vibe that made her feel approachable. It was a perfect mix of her world of growing up without the opulent wealth her friends had and growing up among Manhattan's elite and becoming a part of their world.
Lunch was incredible and Jenny truly thought it was some of her favorite French food even when she lived within hours of being in actual France. By the time they were leaving the restaurant Blair told them it was time to go back to the house and open presents. Serena actually began jumping up and down with excitement. Jenny laughed and thought to herself that for someone who could probably buy half of Manhattan if she chose to, she was awfully excited for gifts. As they got into the limo there was more champagne waiting for them. Of course it was Blair's favorite bottle of Dom. It was truly like she had an endless supply of it at her fingertips. Come to think of it she basically had an endless supply of anything she wanted. Chuck certainly did not know how to say no to his wife. Her safe of jewelry that had to be worth more than the crown jewels of England was evidence of that.
When they walked back inside the brownstone it was evident that Dorota had been busy while they were gone. All the presents were laid out in perfectly wrapped gold and silver packages. Even the presents that Jenny had brought were matching the pile of others. There was also a beautiful cake with a silhouette of the NYC skyline on it. The cake was huge. Much to large for the three of them but that was typical. All Upper East Side events always had far too much food. Serena was truly like a child and could not wait to open her gifts. Jenny had always loved Serena's attitude about life. She really loved the little things and surprises, which was so refreshing for someone that could have and basically did have everything she wanted. The first box she opened was a set of dark blue lace lingerie from Bordelle. Serena squealed and exclaimed that Dan would love it. It was still weird for her to think of her brother seeing Serena in something like than and all that would ensue after the reveal so she tried to forget who these presents were really for. Next was one of Jenny's gifts that was a shear red and black babydoll set from Myla which was not even available in the U.S. yet. The gift opening continued with piles of lingerie and swimsuits that left very little to the imagination. Lily joined them towards the end of the presents and did not even flinch at the collection of intimates her daughter had around her. Jenny had to admire that because she thought she would be embarrassed to have that around her own mother and could not imagine that with a future daughter she hoped to have.
Dan's day before his wedding to the woman of his dreams was going a little differently. He had just gotten his ass kicked at basketball by Nate and they were heading to meet Chuck for drinks at the Empire. Nate thought he may have actually been more jittery about tonight's rehearsal dinner of sorts than Dan was. Dan kept telling him that he was not nervous. He was excited and had been dreaming of this day for far too long to be nervous. Even if it was a complete disaster it did not matter because he would be with the love of his life at the end of the day and she would officially be his. As Dan was telling Nate this on their walk from the park to the Empire, all Nate could think about was that he would feel that way if he got the opportunity to marry the woman of his dreams, his best friends sister and the girl that was no longer off limits. He could not remember a time that he had ever been jumping out of his skin to see someone in his life. 7 pm could not come fast enough.
The men were greeted by the doorman and went to the private elevator to the penthouse which now belonged to Nate because Chuck clearly did not need it anymore. Chuck and Eric were already upstairs waiting for them. In anyone else's world it would be weird to walk into your home and find other people there but on the Upper East Side it was oddly normal. Chuck of course had already started a scotch. He was not quite sure how to throw Humphrey a Bachelor party because he was not really a normal guy. He would not be amused by the likes of strippers or excessive alcohol. Chuck had even offered to fly them anywhere on his Bass jet but Dan said that was not necessary since they were already using it for their honeymoon to Bali. Plus they needed to make it on time to the dinner tonight or Blair's head would explode. So instead they were sitting in the Empire like so many times before. After pouring his own drink, Nate went into his bedroom to grab a few presents they had for Dan. The first was a set of handcuffs engraved with "Dan and Serena December 17th 2017" and Dan actually blushed looking at them, which made Chuck's cries of laughter unstoppable.
"Don't tell me this is your first set of handcuffs Humphrey…" Chuck got out between laughs. Dan said no but he was clearly lying. Chuck's laughing got worse and now Nate and Eric joined in. "There is no way that your fiancé can be best friends with my wife and never had you use handcuffs" said Chuck on the verge of falling over. Dan was now fully embarrassed.
"I guess everyone can't be as weird as you and Blair, Chuck." Nate got out once he could finally catch his breath. Dan was grabbing the next present to hopefully move on to something much less and embarrassing so this incident would be forgotten and never told to anyone. Thank god it was. It was a robe that was very similar to the one Chuck wore far too often with an H embroidered on it. Chuck clapped him on the shoulder and said, "Welcome to the family."
The next small package was from Eric who said, "It's finally your turn to have something we've all had since we were like 12." Inside the box was Dan's very own Black card with his name on it. He had never imagined he would have a credit card with no limits on him. He knew marrying Serena would mean he had an obscene amount of money, even though he had been doing rather well for himself between his books and editing for the Spectator, that was never a motive beyond marrying the love of his life.
"Thank you, Eric" Dan said a little bit in awe. In the next box was an incredible pair of Cartier gold and red cufflinks for him to wear tomorrow. Dan began mumbling something about how these were too much and we could not accept them.
"You are about to officially be a part of our world now, Gossip Girl, you need to learn how to accept gifts properly and expect things such like this. Isn't this what you have been waiting for all these years?" Chuck said laughing at the look on Dan's face when Gossip Girl was mentioned.
"Speaking of Gossip Girl…" Nate also laughed and handed Dan the last of the presents in a flat box.
"I'm scared to see what this is now" said Dan as he unwrapped the present. Inside was a book and on the cover was the infamous picture of Serena in the wet white dress on the Intrepid. The picture that had started it all. The rest of the book was every post and picture that Gossip Girl had documented of the 2 of them, with the last picture being a picture from when Dan had proposed to Serena. Normally something like this would be kind of creepy but it was touching and Dan was happy that someone had spent the time going through the ridiculous number of posts to find all the ones of "S and Lonely Boy." "Thank you all so much. These gifts really mean a lot to me. Even the handcuffs" Dan joked with all the embarrassment set aside. They continued to drink, shoot pool and watch sports until it was time for them to get ready to head downstairs to one of the ballrooms for the dinner.
Jenny had designed all three of the women's dresses for tonight's dinner. Serena's was short, white and lacy. Jenny figured she should wear white at some point in the experience since she would not be for the actual ceremony tomorrow. Blair was wearing a ruby red cocktail dress that was tight up top with a drop waist and a ruffled skirt while Jenny had a navy blue dress with a plunging neckline with a flowing skirt and heart shaped opening in the back. They looked incredible as they got into the limo to head over to the Empire where the event was being held. The location was supposed to be kept secret to avoid any paparazzi from being there but of course when they reached Chuck's hotel there were a few cameras outside. They posed for a few pictures to make it easier on themselves before heading inside. Jenny's heart was beating out of her chest she was so nervous to see Nate after so long. She truly had not felt like that in years and she knew that when she spoke to him she would sound like a bumbling idiot. Blair had made sure they were the last to arrive. Serena walked into the room first since this night was about her after all and Blair and Jenny followed a minute later. As soon as she walked through the door, Jenny was looking for him. She tried not to make it obvious and kept smiling the whole time as she walked over to her seat. Then she finally saw him and she could swear her heart stopped because he was smiling right back at her.
A/N: Ah sorry for the ending I thought it was the perfect place to stop. Don't worry I will update the next chapter rather quickly. Hope yall like it so far and let me know what you think! I would love to hear some opinions!
These are the cufflinks I was talking about Dan getting.
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