Dan entered the world of Gossip Girl as an outsider, nicknamed, "Lonely Boy." He attended the same elite school as Chuck and Nate, but he didn't move in their circle. While he longed for a date with the elusive but beautiful, Serena, she didn't notice him until she returned to New York, ready to make changes in her life.
Presented as brilliant and kind, Dan became a friend to the Gossip Girl group. Although he frequently criticized them, he also benefitted from their association, and at times, he was a huge freeloader. Other times, he showed moments of profound generosity--a generosity of time, friendship, and kindness, rather than money.
10 Huge Freeloader: All Of The Many Parties
As much as Dan may poke fun at his wealthier peers, he also takes part in the parties. These are parties that he and his family don't pay for, and through Serena (and others) he becomes a nearly constant addition. Likewise, at these parties, he meets people who can help forward his career.
Lonely boy may complain of being an outsider, yet he's invited into this privileged world quite easily and consistently.
9 Super Generous: Rufus's Rekindled Romance
When Dan discovers that his dad, Rufus, once was in love with Lily when the two were younger, it's an odd moment, especially since Lily is Serena's mother. Yet, when Rufus and Lily rekindle their romance, he supports his dad.
When that romance flourishes into something more, Dan and his sister notice Rufus eying a ring in a vintage store. They know that their father plans to propose to Lily. Dan warms faster to the idea than his sister, but they both pool their money to buy the ring for their father--a way to show that they support his decision. While Rufus pays them back, this was a sweet and generous gesture.
8 Huge Freeloader: The Internship
In Season 4, Dan gets an internship at W Magazine as does Blair. The reason that Dan got this internship was through Lily's connections. He assumes that Blair also got the internship through her influential mother. However, after he sabotages Blair (something that they had agreed not to do), he learns how wrong he was.
While he got this internship through his now privileged connections, Blair worked to get hers--even faxing her application letter to the 332 machines in the building. He apologizes, and she quickly responds, "What the fact that you were willfully ignorant is supposed to make me feel better? You wanted an internship. I wanted this one."
7 Super Generous: Georgina's Baby
At the end of Season 3, a very pregnant Georgina comes to see Dan and tells him that she's pregnant with their son. In Season 4, Dan grapples with being a father, and he accepts Georgina's story that Milo (the baby) is his son. He signs the birth certificate. His father is warier and discovers that Milo isn't Dan's.
Georgina abandons Milo with Dan. Then Dan decides that if Milo isn't biologically his, he is still willing to raise him, even if it complicates his life. Georgina comes back, confesses, and takes Milo--a pain that hurts Dan as he had gotten attached.
6 Huge Freeloader: Exploited Friendships for Stories and Fame
In Season 2, a jaded writer recommends that Dan get the gritty stories of others and use those stories to write something great. At first, he listens to the writer and asks Chuck for an introduction into Chuck's world. During this crazy day, Dan learns that Chuck believes that his birth caused his mother's death. Despite the writer's urging, Dan decides not to publish the story-not wanting to exploit the dark stories of others for his own personal gain.
If only this were to stay that way throughout the series. His first novel is a thinly masqueraded version of his friends' lives. He acquires fame (and a theatrical performance) due to this exploitation. One could say that it's a memoir because he is in the story as well, but he also benefitted from writing unfavorably about his friends, especially Serena.
5 Super Generous: Advice to Blair About Her Mother
There are many times when Dan was called on for advice by multiple characters in the series. Serena even once brought Blair over to Dan's for advice about Chuck. So why then is this moment in Season 1 stand-out? Why is it generous?
Blair had been told that she was to be the face for her mother's new fashion line. Serena, who was just supposed to be there to support Blair, became the face. Dan overhears their argument, and it's clear that Blair is in pain, and Serena is oblivious that she took the spotlight from her best friend. Up until this point, Dan thought Blair to be what he hated about the Upper East Side. It's in this moment that he realizes that she's vulnerable, human, and hurting. He shares a vulnerable story about his own mother in order to help her find the strength to confront hers.
4 Huge Freeloader: Vanessa's Publishing Connections
Dan wasn't ready to have his novel published, but Vanessa "stole" it from him to give it to a publisher. On one hand, this happened after the two had a fight, and Dan wasn't sure if he was ready for it to be published. On the other hand, Dan had his first novel published easily, and it received acclaim.
He didn't have to shop his novel around or revise it a hundred times. He didn't have to cold-call agents. Vanessa, his friend, had connections, and then it was published. She did the work for him, and he complained about it.
3 Super Generous: Rescues and Believes in Serena
Dan rescues Serena many times and in many different ways. No matter what, he never gives up on her and believes in her when others doubt. One example is in Season 4; it seems like Serena is back to her destructive ways when she overdoses.
She insists that she didn't do it, and initially no one believes her but Dan. Later, Blair and Dan work together to track the real culprit. This is just one example of the lengths that Dan will go to for Serena.
2 Huge Freeloader: Gossip Girl
In the final season, it's revealed that Dan was Gossip Girl all along. As Gossip Girl, he wrote horrible things about his friends and family members (even his sister). He wrote about personal stories, spread rumors, and made their lives difficult.
As much as he shamed Blair and Chuck for manipulating and scheming; ultimately, he was worse. Dan comes across as the villain and the freeloader--making his earlier morals about exploiting the dark stories of others seem strange and hypocritical. On top of this, he suffers no consequences for his actions, and he's forgiven and easily accepted back into the fold.
1 Super Generous: Blair's Trauma and Pregnancy
Dan and Blair become good friends. This friendship becomes even more solid when Blair is set to marry the prince. Blair finds out that she's pregnant, but she isn't sure if the baby is the prince's or Chuck's. Dan supports and encourages her to find out. In the end, he tells her that he'll be there for her, no matter what.
When she has the accident, he is also there for her. Ultimately, when she decides to run away from her "ideal" future with the prince, he rushes to her aid. This is where friendship starts to become a romance. However, regardless of that, Dan gave his time and support to Blair. He became one of the few people that she trusted, and even as Gossip Girl--he kept everything secret.
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January 04, 2021 at 12:30AM
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Gossip Girl: 5 Times Dan Was A Huge Freeloader (& 5 He Was Super Generous) - Screen Rant
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