Five Years Later…

Jenny steps into Starbucks on the way to Waldorf Designs at six in the morning, preparing for another sixteen-hour day preparing for Fashion Week and hosting the kick off party. She's exhausted, but she this is the first year in the three years she's worked at Waldorf that Blair is letting her lead the designs for the biggest week in fashion. It's a huge deal and she's honored beyond belief that her friend trusts her so much.

Her phone rings as she's standing in line and a picture flashes on the screen. She answers the phone with a grin.

"Hey," she greets.

"Hello, my love. I'm on my way to the office, but I wanted to make sure we are still on for lunch today. I'll swing by and pick you up? Then after lunch we'll head right over to the Waldorf party?"

"Yeah, definitely. I have something to talk to you about anyway." Hopefully, he'll be happy with her news.

"Great," he says, and she can hear the smile in his voice. It is mirrored on her face. "I'll see you at noon then."

"Okay, love you."

"Love you, too."

When she hangs up the phone, her tea is ready. As she is walking out of the store, she collides with a woman walking in. Luckily, she is able to save most of her tea, but some spills on her blouse.

"I am so, so sorry," the woman says as Jenny runs to get some napkins.

And Jenny freezes, because she knows that voice. When she looks up from drying herself off, her fear is confirmed. There stands Serena Van Der Woodson in all of her glory. Serena is smiling, a real smile this time. "Jenny Humphrey! Oh my god, I can't believe it! How are you?" She hugs Jenny gently before pulling away. Jenny shifts awkwardly on her feet, tucking her shorter blonde hair behind her ears.

Serena has been gone for six years. Eric has said that she is doing well working movie producer in California. She doesn't really keep in touch with Nate or Chuck or even Blair. But now she's here. She's back in Manhattan and it terrifies Jenny.

Jenny continues to shift awkwardly on her feet, her heels suddenly feeling like they are forcing her to be off balance. "I… I'm good. How are you?"

"Amazing. I'm living in LA still, just here to visit my mom and Eric and take a vacation from work for Fashion Week!"

They continue to chat for a few minutes and discover that they are going in the same direction, so they walk together. Jenny is shocked to find that she can't help but like this Serena. She's funny and sarcastic and not trying to threaten Jenny. For the first time, she can see what everyone else sees in Serena.

"I… I was thinking of going to the Waldorf party this afternoon. Would that be okay?" Serena asks almost shyly as they stop in front of the building she is going to. Jenny smiles.

"Sure, I'm sure Blair would be thrilled to see you! I'll add your name to the list. Do you need a plus one?"

"No, just me. Are you sure? I know that you and me have a history and whatnot… and, well, I'm sorry. I just really want to support you and Blair." Suddenly the taller girl looks nervous.

"It's fine. It was a long time ago." And Jenny finds that she means it. Her life is so good now that she can't even imagine going back to the girl she was all those years ago. And she figures that Serena deserves the same chance to evolve.

"No," Serena says emphatically, her hand touching Jenny's arm. "It isn't fine. I was such a bitch. I was horrible to you and you didn't deserve it. Nate didn't deserve it either. If I get the chance to see him while I am here, I'm going to tell you the same thing. The thing is, Jenny, I was so threatened by you. Nate loved you so much and I was so insecure because I knew he loved you more than me. It made me angry – it was the first time someone else was wanted more than me. But I've grown up and I realize how ridiculous it all was. And I am so sorry."

"Well, thank you for the apology, but we've all moved on and grown up – it really is fine. And if you're going to the party, you'll see Nate there. He's on the board of Waldorf Design and his paper covers Fashion Weeks events every year." She tucks a blonde curl behind her ear with her left hand, showing off the sparkling diamond on her ring finger and the platinum band that complements it. "Plus, as the lead designer's husband, he has a duty to be there."

Jenny smiles now, thinking about her supportive husband. The Spectator is so busy but he still never misses a Waldorf Design event. Serena looks surprised, but not angry.

"Wow – you and Nate are married? That's amazing!"

"Yeah, it's been just over a year. I… we eloped actually. Chuck, Blair, Dan, Eric, and my parents were the only people there. I can't believe Eric didn't tell you."

"Well, he knows our history and probably didn't want to start anything. It doesn't matter, I'm happy for you, Jenny. Really. You and Nate have always been great together."

She can tell that Serena really means it. And she finds herself actually admiring the older girl's maturity over the situation.

"And what about the famous heartbreaker Serena Van Der Woodson? Has anyone managed to tie you down yet?"

"No! I… there was someone for a while and I thought we had something real, but he moved to New York actually so it ended. I thought I loved him too."

"Well, you're here now, so maybe you'll see him," Jenny offers.

"Maybe…"

They continue chatting for a few more minutes before hugging and going their separate ways. Jenny is smiling when she enters Waldorf Designs and, of course, Blair notices right away. When little Henry comes teetering out of Blair's office to see his Auntie J with his mother behind him, the blonde just watches her best friend as she nurtures her baby boy. So much has changed, she thinks as she picks up her godson and gets interrogated by her best friend. But she wouldn't have it any other way.

She gets to work on the finishing touches and forgets to think about lunch or the party as she hems and evaluates each outfit. They are amazing (in her not at all biased opinion). Blair says this collection will change Waldorf Designs forever and make a name for Jenny. It is a beautiful collection – inspired by gems and jewels. Each outfit is in jewel tones and actual gems are incorporated. It was inspired by the blue of Nate's eyes, which reminds her of sapphires. The silhouettes of the pieces are edgy and contemporary, but still feel classy as all Waldorf Designs clothes are. Jenny just hopes the media and critics love it as much as she and Blair do.

At eleven fifty, Nate comes walking into the studio, a bouquet of roses in his hand. Always the romantic, her husband. Her heart still flutters when she sees him walking into the room, even after all these years. He's wearing a suit and tie, but she can still see the boy she knew who wore jeans and tee shirts and had shaggy hair hanging in his face. He greets her with a kiss and a smile and she can't help but feel like she is floating.

At lunch, they request a secluded booth and spend more time wrapped in each other than they do eating.

During dessert, she tells him the news. He actually tears up, he's so happy. He laughs and smiles and hugs her close.

When they leave, there are a couple reporters waiting, asking if he is going to run for mayor, as has been speculated. They've talked about his career in politics, given his family history, but he wants to think about it and wait until they are more settled. Jenny has agreed – it's too soon, they are much too young. So he once again denies it, but he does announce that he is going to be a father in just a few months.

The reporters go wild. They snap a picture of the couple with his arms around her waist and his hands resting on her stomach. It will run in the papers tomorrow, the reporters say.

At the party, Jenny declines champagne and Blair immediately knows. She hugs her best friend close and tells her how excited she is – because they are going to have babies together! When she discovers that her best friend is pregnant, too, Jenny squeals so loud that their husbands come over to check on them. Chuck is carrying his son, who is wearing a bow tie, and the two couples congratulate each other.

Dan shows up at the party, fresh from three years in California. He's just finished his new book and he decided to move back to New York to teach creative writing at NYU. When Jenny tells him the news, he's thrilled.

Vanessa isn't there. She and Dan broke up four years ago and since then Vanessa has been traveling the world and 'finding herself.'

They party is in full swing by the time Serena arrives with her mother, Eric, and Eliot. But, of course, all eyes are on the blonde bombshell as soon as she walks through the door. Except Nate's. Those baby blues are planted firmly on the woman standing next to him. She is radiant and he can't help but fall more in love with her every day. Her hair is shorter and her face is fuller, but she is still the girl of his dreams.

And now she is giving him the greatest gift of all. A baby. He's going to be a father. He is sure as hell that he is going to do a better job than his parents did because there is real love in their home.

Jenny no longer feels threatened by anyone, even the mystical Serena. Nate loves her more than anything. She knows that no matter what happens, he is hers just as much as she is his.

She is all smiles and lets Serena speak to Nate privately so she can apologize. Within minutes, he is back at her side, letting her know what Serena had to say. It feels nice to have closure to that chapter in their history.

And then Serena sees Dan as he comes over to give Nate the beer that he got him.

She drops her glass of champagne and he looks like he has seen a ghost.

Jenny can't believe her eyes. Serena is stumbling over her words and Dan is silent. Neither of those things ever happens. They stare at each other.

Jenny and Nate are surprised. Nate leans over to whisper in her ear, "What do you think is going on with those two? I didn't even know that they kept in touch." Jenny shrugs.

But Jenny just knows. She can see it in their eyes. Dan and Serena are in love.

It turns out that Dan is Serena's California boy. He left her for the teaching job in New York and broke her heart. But she still loves him and his sister knows that he still loves her as well. So she gives him a much needed pep talk and watches as her brother approaches Serena, takes her hand, and pulls her to a corner of the room where they quickly fall into conversation.

Her husband takes her hand and escorts her to the dance floor, smoothly guiding her in a slow dance.

"Looks like everyone gets their happy ending," she whispers, looking back at Serena and Dan and then Blair and Chuck, who are dancing with their son.

"Looks like it," Nate says before leaning in and meeting her lips with his.

The End.