I have recently become obsessed with Gossip Girl. I'm bingeing on Netflix right now, on Season 5. I fell in love with Nate and Jenny and I was disappointed with the way they were portrayed and their relationship played out. So I am channeling that frustration into writing. This short story is completely written and I already have another one in the works. I own nothing but the plot. Please enjoy my first foray into GG fan fiction!

They are dating. They love each other. You're nothing but a distant memory. A friend. Someone he has to take care of. He'll never look at you like he looks at her. Jenny's mind won't shut up, the thoughts just keep echoing. Seeing Nate walk down the street hand in hand with Serena makes her lose her breath. He looks good, better than she even remembers. His brown hair is a little shorter than it used to be but it's still just as messy, like he just woke up. His blue eyes sparkle as he talks to his girlfriend, a smile lighting up his face.

Most of all, he looks happy. Nothing like the mess that Jenny is.

…

Jenny met Nate on a warm August day when she was a freshman in high school and he was a sophomore. He was a new friend of her brother, Dan, and he quickly became a regular fixture in her family's Brooklyn loft. Apparently, his parents weren't home much and Dan took pity on him, inviting him to family dinners, movie nights, and their dad's concerts. Jenny liked him. Despite his Upper East Side upbringing, he fit in in Brooklyn. His shaggy hair and relaxed personality molded well with the hipsters that lived over the bridge. And, more importantly, he fit in with the Humphrey family.

When Dan started dating Vanessa, he had less time for Nate. But Nate still didn't have a real family and had already adopted Jenny's, so he was still around all the time. Jenny didn't mind. He was nice to her, noticed her, and looked out for her. In return, she made him laugh and idolized him.

She may have had a slight crush, but knew nothing would ever happen. He was with Blair, he had been since he was fourteen, and he loved her. Plus, Jenny was like a little sister to him. So she swallowed her feelings and became very good at hiding the truth. She'd rather have him as a friend than not have him at all.

Within months of Dan ditching the two of them for his girlfriend, Nate and Jenny were best friends.

Blair and Nate would fight and Jenny would comfort him, telling him that he deserved better than Queen B, that he deserved someone who would treat him right. He'd smile and ruffle her hair before turning back to the movie on TV.

She'd get a bad grade in chemistry and Nate would tutor her, helping her understand the atomic makeup of oxygen and hydrogen and more. He'd hug her when she aced the next test.

They both liked action movies and books and laughed at stupid things. They enjoyed walking and running in Central Park. Jenny joined him on those rare occasions when his father was around and the trio would run in the park.

Jenny helped "style" Nate and, in return, he gave her advice about school, her family, and life.

They liked the same music. Jenny would never forget when he took her to her first concert at Madison Square Garden. She had never smiled so hard in her life. The band's t-shirt was a staple of her wardrobe. The selfie they took that night, with both of them radiantly happy and disgustingly sweaty, was the background on her phone.

He met her every morning on the steps of The Met, a vanilla latte with her name on it in his hand and a smile on his face. She greeted him every morning with a hug and a kiss on the cheek. Blair often joined them, smiling to Jenny's face and glaring at her when her back was turned.

When she found out that Blair was cheating on him with his (other) best friend, she had to tell him. It made her sick that someone as good as Nate could be treated so terribly by someone that said she loved him. She kept it in, she didn't want to be the one to break him, but he discovered it anyway. He told her that felt betrayed – she knew and she didn't tell him. She was supposed to always be on his side.

She called a hundred times, leaving voicemails explaining that she just didn't know how to do it – how to tell him. That she didn't want to hurt him. That she cared.

He texted her back that he'd lost his girlfriend and both of best friends that night. And it fucking hurt him.

It took a week for him to forgive her. But eventually, he gathered her into his arms and kissed her hair, telling her he was sorry for taking out his heartbreak on her. She bought him ice cream and chips and they went to the roof of his building to share a joint and the snacks. It was the happiest she'd been since the day he found out.

A few days later, he told her that he didn't think he'd ever really loved Blair. She was convenient and his family adored her. So he stayed with her way past their expiration date. But it was over, and he was done being heartbroken over it.

After that, they spent even more time together. Nate would sleep over – Rufus insisted that he bunk with Dan or sleep on the couch ("it doesn't matter that you're just friends, Jenny, he's a teenage boy with hormones and you're my little girl," her father would say to her). They had all day movie binges and he took her out on his beloved sailboat. At school, she would walk with him, purposefully ignoring his former friends.

Eventually he forgave Blair and Chuck. They were good together, he decided. They were inevitable. Meant to be. Just like we are, Jenny caught herself thinking when he told her that. And when they had lunch with the new couple, Nate said he was happy for them. Blair smiled at Jenny for the first time that day. They became friends. Once they were no longer vying for Nate's attention, Blair was actually sweet and took Jenny under her wing.

Everything was sunshine and roses until Serena Van Der Woodson returned to the Upper East Side.

At the beginning of Jenny's sophomore year, and Nate's junior year, Serena waltzed back into their lives, fresh back from a year in boarding school.

Jenny couldn't help but be jealous of the blonde. She was taller, slimmer, and more glamorous than Jenny would ever be. She'd known Chuck, Blair, and Nate their entire lives. She was an insider, and Jenny knew she would always be on the outside.

But Jenny had Nate. Until she didn't.

It was revealed that Nate had slept with Serena before she left for boarding school. He'd lost his virginity to her and always loved her, even though he was with Blair. Jenny would watch as Nate followed Serena like a lost puppy, begging for her attention.

He stopped coming to Brooklyn, choosing to spend time with Serena and her family instead.

Jenny felt betrayed.

One night, when Jenny was on the phone with him, he told her that he'd asked Serena to be his girlfriend. Serena had accepted with a kiss and a squeal. Jenny let silent tears fall as she told him how happy she was for him. When Dan asked what was wrong, she told him she stubbed her toe.

She and Nate continued to drift apart. Soon, she only saw him when he was hanging out with Dan before soccer practice. And he never really talked to her; she was just kind of there. Dan and Vanessa went on double dates with Nate and Serena and they were so fucking cute that Jenny wanted to throw up.

And the hole in her heart continued to grow.

The last straw came when she was hanging out with her friend Erik, who happened to be Serena's brother. He too was overshadowed by his popular, alluring older sibling, and the two immediately bonded. He was the only person in the world who knew about her crush on her ex- best friend. That fateful day, she walked into Serena's room to ask her a question for Erik when she saw them.

Nate was shirtless, laying on top of Serena, who was in her bra and panties. They broke apart when she gasped and apologized for barging in. Nate's cheeks went red and he jumped up, awkward and embarrassed and reaching for his clothes. Serena didn't even blush. She just gave Jenny a snide look that said it all.

It said: he's mine.

And Jenny broke. She ran out of the room, ignoring Nate's calls after her. She took the train back to Brooklyn and asked her dad if she could go to Hudson and stay with her mom for a while. Rufus, overwhelmed by his teenage daughter sobbing with mascara running down her face, agreed.

She was on a train to Hudson the next day. She didn't say goodbye to anyone but her family. But she cried all the way to her mom's house.

Where are you, Jen? Nate would text. She ignored all of them.

She started at a new school, made new friends. Met a boy named Tyler and tried to forget that Nate and the Upper East Side existed.

Dan came to visit one weekend and Nate tagged along. He looked like a stranger in his fancy clothes with his shorter-cropped hair and Sperry's. He was no longer her best friend. He didn't make her laugh anymore. Instead, she just hurt inside when he was around. He innocently asked her what was wrong. The look of concern and sadness in his eyes made her break even more. So she ignored him. He went home and didn't text again.

A year passed before she went back to Manhattan. Her mom was going to Paris for a year to run an art exhibit at the Louvre, which was an amazing opportunity, so Jenny didn't have a choice but to move back to Brooklyn and return to her school. She didn't cry when she left Tyler or her friends. By this time, she was a senior in high school and Nate was gone. She heard from Dan that he was at Columbia. She breathed a sigh of relief that she wouldn't have to see him every day.

But he was Dan's roommate in an apartment halfway between Columbia and NYU. She didn't know until the first time she went by the apartment and saw Nate there, getting out of the shower. She'd stumbled and stuttered, asking if Dan was home. He said no and offered to let her wait. She declined and ran out of the apartment. She didn't catch her breath until she was home.

Her heart never healed. She was alone and angry. When she graduated high school, she decided to go to Columbia despite his presence on campus because they had a good business program and she already had the fashion skills, she needed the business skills. She got an internship at Waldorf Designs, working for Blair's mother.

She worked and went to school, but her life was empty. Blair was around and so was Dan. But Blair was Serena's friend, so it was awkward. And it wasn't like she could talk to Dan about her problems. He'd worry too much. At least she was able to avoid running into Nate.

She was alone.

…

So when she sees them on the street, laughing and smiling, her broken heart doesn't shatter anymore. She doesn't hurt. It's been too long. She's just hollow now.

He freezes when he sees her. Serena looks startled, looking around until she locks eyes with her. The blonde's eyes narrow. It's clear she isn't happy about Jenny's unplanned reappearance in their lives.

Jenny swallows as they approach. She can't help but notice that he releases Serena's hand as they get close. Then she kicks herself for even caring.

"How are you, Jenny?" he asks, sadness filling his bright eyes suddenly. Does he look remorseful? No, it isn't possible – she is positive that he has no regrets. He is with his one true love. They've been together for two years.

"I… I'm okay. How are you?"

"Good," he says. "Dan said you were at Columbia, I was wondering when I would see you around!" He sounds cheerful and there is a smile on his face, but it doesn't reach his eyes.

It isn't like the smiles he used to send her way, back when they were friends.

Serena is silent, texting fiercely on her phone as Nate chats with her. Jenny can feel the hostility coming towards her in waves and she knows Nate feels it too. It's uncomfortable to talk to him, especially with Serena just there, observing them.

So she finds an excuse and leaves.