A/N: This suddenly came to me so I decided to make this. It's mostly talking about what already happened in Gossip Girl but the ending part is the part I made up about what happens in the future. Please R&R!
Disclaimer: I don't own Gossip Girl!
Jenny Humphrey used to be sweet and innocent. Just a regular Brooklyn girl who had no place in the high life of the rest of the Upper East Siders. Because right then she was content with just being the sweet little sister to Dan Humphrey, the daughter that Rufus Humphrey wanted and was proud of, and admirer of Serena Van der Woodsen. Because at the time she didn't care that she wasn't noticed by Nate Archibald, the Prince of St. Jude, that she didn't live the high life the rest of the kids at Constance and St. Jude lived, that she was unnoticed by everyone that was someone.
Then one day Jenny wasn't content with being who she was. She didn't want to be little sister to Dan, she didn't want to be the daughter Rufus wanted because she no longer wanted to be that girl, Jenny didn't want to admire Serena; she wanted to be Serena. The girl that the boys all wanted and the girl that the girls either wanted to be or be friends with. And she cared now about Nate not noticing her because she liked him and wanted him; she wanted to be the Princess (or Queen. It didn't really matter as long as she had him) to his Prince. She wanted the glamorous life that the others had. Jenny wanted to be noticed.
So Jenny slowly changed herself and things changed around her. She wasn't Dan's little sister anymore because she wasn't noticed much because her brother managed to snag the Serena Van der Woodsen. She's pretty sure the only reason she got a spot in the little group known as Blair's minion was because her brother was dating Serena and Serena was Blair best friend. But Blair didn't like her and neither did her minions. And she was finally noticed by Nate, just not the way she wanted to be. She wanted him to want her the way she did. He only had eyes for Blair Waldorf and Serena Van der Woodsen. So Jenny just kept on changing because it wasn't enough because she kept on wanting and wanting more things each time.
Soon Jenny had changed so much she hardly recognized herself and things kept changing alongside her. She now acted like the Upper East Siders to fit in, she wore tons of makeup to be as pretty as the other girls, and she did everything to fit it. And suddenly she was Queen of the Upper East Side. But that wasn't enough for her; nowadays she felt that nothing was ever enough. But not everyone adored her like they adored Blair when she was queen. Nate was nicer to her (she was glad they were still friends even though they didn't work out but she still wanted him) but she could tell he still liked Blair and Serena better (she was pretty sure he always would no matter what), more guys noticed her but it was lust not love like it was with Serena. She tried (she really did) but no matter how much she tried her father was never happy with the new her. It was never enough for her. She wanted everything to be perfect for her the way it was with others in the Upper East Side.
It was then Jenny realized the lives of the Upper East Siders weren't as perfect as she thought. People betrayed each other to get to the top; to get the better life, they lied to get what they wanted, and they did everything that proved the UES life wasn't perfect. But she wanted the perfect life. But she didn't get it. Instead to Jenny it seemed like everyone around her got the better things. Rufus got his dream girl, Lily Van der Woodsen, Dan had Vanessa to cheer him up and help him move on about Serena, Blair and Chuck had each other, and no matter how much she didn't want to admit it; Nate got the girl he's wanted since the masquerade ball, Serena. So where did that leave Jenny? She was pretty sure her so called "minions" were watching closely to find a mistake she made so that they could dethrone her and bring back Blair. She messed up her friendship with Eric, Serena, and Dan. Her life was far from the perfect life.
Jenny had completely messed up everything. After realizing that she would never have Nate especially since she was sure he and Serena would get back together anyways (but like always she still wanted him) she slept with a heartbroken Chuck. But Blair came back to Chuck the way she always did but Nate never came for Jenny. So she just left. Then what she had done had finally sunken in so she told what happened. And she ruined things for herself. Dan had made a big deal and stormed to where Chuck and Blair were. He had punched Chuck and it all went down from there. Blair had sent her away, banished her away for Upper East Side; the place she loved despite how things turned out for her. So she left for Hudson to go live with her mom and left her wonderful Upper East Side.
It had been a year since she had been banished from Upper East Side. But she still read Gossip Girl to see what was going on. And one day she went on and wanted to cry. Nate had finally proposed to Serena, the two had fixed things between them awhile after Jenny had left and were happily in love. Chuck and Blair had a harder time fixing their relationship but they managed it because they were a match made in heaven. He hadn't proposed yet but there were rumors that he was going to. Dan and Vanessa had just started dating but they were still happy and were acting as if they had been long lost lovers. She thought it was unfair that everyone else was having their fairy tale ending but her, especially since she was the one who had so desperately wanted one in the first place. And as Jenny looked back, she realized she wished that she was still the sweet and innocent Jenny she once was. She wished she was the girl she once was.