The CW's Gossip Girl has been over for almost a decade, and fans of the CW drama are still torn about who Dan — or should we say Gossip Girl — should have ended up with. In the polarizing season finale, the self-proclaimed Lonely Boy marries the love of his life, Serena, even after revealing to her that he was behind the terror that Gossip Girl had unleashed on the wealthy students of the Upper East Side.
While Derena may have won, Danessa fans are still quite adamant that Vanessa was the girl for Dan. The novels wrote Dan and Vanessa as endgame, which made a lot of sense since they had known each other longer, developed feelings for each other earlier, and understood one another. However, the show depicted the fairytale(ish) romance between the poor Brooklyn boy and the privileged yet rebellious Upper East Sider with great flair. So, did Dan make the right choice? Or was Vanessa the one that got away?
Vanessa: Dan's First Love
When Vanessa arrived at the Humphrey loft, things were a little awkward for her and Dan. Before she had left for Vermont with her parents, Dan had confessed his romantic feelings to her, which she had rejected at the time.
Vanessa was Dan's first love, and their affection for each other grew organically and wholesomely over the years. While Vanessa may have turned Dan down initially, she accepted her feelings for him later and they had a mutually supportive relationship for a while.
Serena: Dan's True Love
Although Dan had a crush on Vanessa first, he fell deeply in love with Serena after they met briefly at a school party. The kind of love that Dan and Serena shared was a very passionate one, and they were both enamored with each other once they went on a few dates and began a relationship.
Both Dan and Serena went to great lengths to sabotage each other, foil each other's plans, and send tips to Gossip Girl (which would be Dan sending tips to himself), but they had a once-in-a-lifetime kind of love which was why they were endgame.
Vanessa: Similar Backgrounds
Vanessa's biggest asset as Dan's partner was that they had a similar upbringing, which enabled them to understand each other deeply. Both artists were born in Brooklyn with more or less the same economic background, which meant that there was no pressure between them to bridge the gap of status.
Vanessa knew what Dan desired and what motivated him to act the way he did because she had been through the same things in life herself. They both had a healthy distaste for the world of the Upper East Siders, which made them perfect for each other.
Serena: Fulfilled Each Other's Needs
Both Dan and Serena lacked certain things in life. Serena thirsted for love and approval, which she never got from her parents — her father had abandoned her and her mother was quite awful to her. Her friends slut-shamed her and she had to live with some bad choices. Dan too craved love, along with company and validation of his talents.
When Dan and Serena met, they fulfilled each other's needs for love, approval, warmth, and a measure of control over their lives.
Vanessa: Made Dan's Career
Nobody helped Dan with his career like Vanessa. Manhattan's Lonely Boy was a writer who couldn't wait to get published but lacked the confidence to do so. In season 1, Vanessa sent Dan's story to The New Yorker, which they published, and later in season 4, she found his novel about the Upper East Side, which she managed to get published by Simon & Schuster.
Vanessa not only supported Dan emotionally, but she also made sure he got his place in the spotlight. As a partner, she was bolstered by his career, too.
Serena: Accepted Dan's Flaws
While Vanessa and Dan ended their relationship because they were too manipulative with one another, Serena accepted the worst in Dan. Anybody else would have run in the opposite direction when they found out that their partner was Gossip Girl, but not Serena. Dan had humiliated Serena, revealed her secrets, and spread terrible rumors about her as Gossip Girl, yet she decided to stay with him and make their relationship work.
While it was also incredulous that Serena stuck with Dan after the havoc he had wreaked on her life, it spoke volumes about her devotion to Dan — whether he deserved it or not.
Vanessa: Understood Dan's Creativity
The two Brooklyn lovers had a lot in common. Vanessa and Dan were both artists — Dan was a writer and Vanessa dabbled in fine art and filmmaking. Shared interests between the two made for a fulfilling relationship where Vanessa understood Dan's creativity and gave impetus to it wherever she could. While Dan didn't do much for Vanessa (in fact he impeded her chance at a scholarship out of jealousy), Vanessa made sure that Lonely Boy/Gossip Girl's prose saw the light of day.
Serena: Opposites Attract
Serena may belong to a different world than Dan, but as the old adage goes, opposites attract. Serena was part of the glamorous Upper East Side, with her connections and parties, while Dan belonged to a middle-class Brooklyn family.
However, Serena gave Dan an entry into the seductive world of the rich and famous that he so desperately longed for. She showed him a different side to life and gave him the chance to associate with people he wouldn't have met otherwise. The Upper East Side was the primary subject of Dan's successful novels.
Vanessa: Childhood Friends
The warm progression from best friends to lovers was natural and wonderful for Dan and Vanessa. They had a special bond that started in their childhoods, which gave Vanessa an edge over Serena. Vanessa had watched Dan grow up and understood who he truly was, as Dan did with her. They knew each other's families and histories, which helped avoid any nasty surprises in the relationship. They were very functional and healthy before they got involved with the Upper East Siders, which was a shame.
Serena: Put Dan First
While fans may think that Dan didn't deserve it, Serena always put him first. Right from the start, she made sure that he had what he needed, sometimes at her own expense. Right from the first date, she supported Dan when he got an SOS from Jenny at the Kiss on the Lips party, even though she was trying to avoid the party herself.
Serena teamed up with Vanessa to give Dan a Christmas gift he would really want, and put him on a pedestal sometimes because of his writing talent. Serena made Dan her top priority, and never stopped loving him, which is why they were meant to be.