Because his parents weren't millionaires, Dan Humphrey was one of the most relatable characters on Gossip Girl. We looked into the elite world of Upper East Side through his eyes and we were all mortified when we learned that he was the infamous Gossip Girl all along.
Since he was the destructive force that toyed with the private lives of Serena, Chuck, Blair, Nate, and even his sister Jenny, it's hard to say that he has any redeemable qualities. Dan Humphrey AKA Lonely Boy was a pretty sad character; a young man, obsessed with the idea of getting the prettiest girl and having as much power as those he surrounded himself with.
10 He Shared A Sibling With Serena
Of all the people in the world, Dan fell in love with Serena, the daughter of his father's supposed soulmate, Lily. What are the chances of that happening? What's even worse, Serena and Dan share a sibling: Scott Rosson is Rufus's and Lily's love child. He briefly appeared in seasons 2 and 3, his plotline being one of the most redundant and hated on the show.
Even if Scott didn't exist, Dan and Serena still had to come to terms with their parents being in a committed relationship. Technically, they were step-siblings.
9 He Felt Like An Outsider
Dan built his whole persona around being an outsider. Dan's best quotes often reflect that this is how he perceives himself: "You’re no one until you’re talked about." Additionally, both Dan and Jenny felt like the poor kids, just because they rode the train to school. Realistically speaking, their loft in Brooklyn suggests that they belong to an upper-middle-class family.
The fact that he felt like an outsider wouldn't even be such a bad thing if Dan didn't see it as such. Considering all the drama and unhealthy relationships in the world of the Upper East Siders, being an outsider doesn't sound too bad.
8 He Watched Jenny's Life Crumble
Jenny was a truly tragic character since she was only fourteen years old when the show kicked off. Dan cared about his little sister, but there was almost nothing he could do to protect her from the harsh reality of Constance, and above else, herself.
While Dan was also involved in several scandals and mean Gossip Girl blasts, Jenny was at the forefront of all the gossip. Her frenemy status with Blair certainly didn't help her mental well-being. When it comes to everything Jenny had to go through because of Gossip Girl, it really doesn't make any sense that it was her own brother plotting her demise all along.
7 He Didn't Have A Best Friend
Dan didn't have any friends, at least no such friends that truly empathized with him. The closest friend he ever made was Nate, but calling them real friends would be a stretch.
No wonder Dan was so fixated on infiltrating the high society since that would at least mean that it looks like he has friends. Dan truly was a Lonely Boy, and it's no wonder he became the Gossip Girl since he didn't actually care about anyone but himself.
6 He Was Bullied By Blair
From the second Jenny introduced Dan, Blair didn't like him and didn't want Serena to be with him. She was always condescending towards him, trying to humiliate him like the true bully that she was. For example, she started a rumor about Dan and Rachel Carr in season 2. Despite everything Blair has done to him and Jenny, Dan still wanted to be friends with her.
Later on, the two realized they shared a lot of common interests and ended up having a romantic relationship, kept on the hush-hush. Hooking up with Dan was one of the most annoying things Blair ever did, and it made both characters seem very inconsistent.
5 The School Didn't Appreciate His Talent
Dan was an avid reader in his spare time, so it's no wonder he also made for an excellent student. Unfortunately, the school prioritized those students who had rich parents, which meant that students like Nate and Chuck got priority treatment, even though they didn't necessarily deserve it.
Nate automatically won the Dartmouth usher assignment for Ivy League mixer, even though he never even showed interest. Despite his talent, the school didn't treat him fairly.
4 Serena "Cheated On Him" And Ran Away
Serena was the ultimate femme fatale for Dan, especially because of all the drama that came with her. In the season 1 finale, she lied to him and told him she cheated on him just to get him to break up with her: "Maybe I want to break up with you. Maybe I can't just let it go. You lied to me over and over and it was easy for you," Dan told the beautiful blonde.
No couple went through as many unnecessary ups and downs as Dan and Serena. While there are many reasons why we should all feel sorry for Serena, Dan didn't have it easy either while he was dating her.
3 He Was Tricked By Georgina
Georgina first entered Dan's life in "Desperately Seeking Serena", introducing herself as Sarah. Dan was so easy to manipulate, so he was probably Georgina's biggest victim. After all, this vindictive lady lied about being pregnant with his child.
If it wasn't for Rufus and his basic knowledge of genetics, Dan would have raised baby Milo without ever knowing he was actually the son of a random Russian hook-up.
2 He Became The Type Of A Person He Despised At First
Dan despised Blair because she was manipulative, Chuck because he thought he was better than anyone else, and everybody else because of their entitlement.
It turned out that Dan was just like them, if not even worse. The show always made the villain of one of the "poor" characters, which sounds like something from Agatha Christie's Poirot. Self-righteous Dan transformed into someone just as manipulative, selfish, and entitled as the squad from the Upper East Side.
1 He Will Never Be Inside
No matter how much Dan tried, he could never truly be "inside". He devoted his life to making it seem like he is one of them by including himself in numerous Gossip Girl blasts, which is pretty pathetic and a little bit psychotic.
With the exception of Serena, there is no way Dan will ever form meaningful friendships with people like Blair and Chuck - especially when it turned out that he was the cyberbully who almost ruined all of their lives.
"gossip" - Google News
December 17, 2020 at 12:30AM
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Gossip Girl: The 10 Saddest Things About Dan, Ranked | ScreenRant - Screen Rant
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