Gossip Girl begins with the return of Serena, the resident "it" girl, back to the Upper East Side. No one knows why she left and why she returned, but two guys are especially interested in her. We have Nate, her best friend's longtime boyfriend, who harbors affection for her. Once intimate with her, Nate wonders if she left because of him. Then we have Dan who has liked Serena for years, but he has only been able to admire her from afar until now.
While ultimately Serena falls more for Dan, eventually ending up with him, who was really better for the beautiful "it" girl? Was it Lonely Boy (Dan)? Or the Upper East Side Prince Charming, otherwise known as Nate?
9 Nate: Comes from the Same World
Nate and Serena grew up in the same world of the Upper East Side. Because of this, they understand its culture and each other's backgrounds. They both come from wealthy families, which makes it seem that they were born with more advantages than others. However, they also understand the pressure and corruption present in that world.
On top of this, they grew up together. This means that they have shared memories, a true knowledge and understanding of each other, and the same group of friends.
8 Dan: Comes from a Different World
While it's good that Nate and Serena come from the same world, Dan expands Serena since he has had other experiences. At the time when we first meet Serena, she is tired of her pretentious world and thirsts for something different. Dan represents that something different.
Serena never judges Dan for his background, and she actually sees him as better than others from her background. To Serena, Dan's world seems more real and sincere. She can let her hair down more there. Visiting Dan in Brooklyn doesn't feel like slumming it (as her friend, Blair, suggests), but coming to a place where she can be more uniquely herself away from the family role that she has been frequently forced to play.
7 Nate: Not Judgmental
A big vice that Dan has is that he is pretty judgmental. Nate is the opposite. He is open to meeting others and doesn't judge them. All around, Nate is an accepting person. While sometimes Nate can seem a little more innocent than other friends in their group, he believes the best in others.
However, even when he learns of vices, he gives people chances. He does love Serena, despite all of her vices. This means that he sees her as a real person, rather than the popular pretty girl on a pedestal.
6 Dan: Is Intelligent and Challenges Her
Dan is very smart, and he challenges Serena to be better in many ways. He talks about their income differences and makes Serena acknowledge her privilege. Making things better, Dan encourages Serena when shes goes for career opportunities.
Since Serena is a beautiful and fun-loving person, others don't notice her other qualities. Dan sees that she is kind, and that she is smart. By being with Dan, Serena is forced not to settle for the easy road. Her relationship with Dan causes her to grow.
5 Nate: Is Her Friend Above All Else
Serena's relationship with Nate started in friendship. In some ways, this makes it a healthier relationship than the one that she has with Dan. Even if she and Nate aren't together, he will always be there for her. Nate values Serena's friendship. While we could say many things about Nate, one of his strongest qualities is his sense of loyalty to his friends. He would be there for them in a heartbeat.
In contrast, Dan has always seen Serena as a potential romance. He hasn't gotten to know her as a friend. Although he cares about her, it isn't exactly the same.
4 Dan: Is Willing To Become Part of Her World
While the last season complicates this point, the first seasons show a Dan willing to put up with snobby people and awkward encounters for Serena. It's clear that those in Serena' s world don't think highly of Dan. Although he probably wants them to like him, he still stays true to himself. This means that he isn't going to sacrifice who he is just to belong to that world.
However, he puts himself in situations that aren't comfortable or welcoming in order to be there for Serena. He's willing to become a part of her world for her.
3 Nate: Doesn't Scheme
Dan may claim the moral high-ground, but he is a master schemer (as we find out more towards the end of the show). Nate, on the other hand, rarely schemes.
He may be conflicted about his desires, as he once was between Blair and Serena, and he may be used by others, but overall Nate is pretty honest. When we compare him to his peers, Nate definitely comes out ahead in this department.
2 Dan: Adored Her For Years
Dan has always had a thing for Serena, and he adored her from afar for years. She even became a muse to him when he wrote a story about a first time that they met a couple years before Gossip Girl. When they finally become a couple, he is incredibly romantic with her. Additionally, Dan stirs the romantic in Serena, and she does incredibly romantic things for him.
One example is when she creates winter for him for his Christmas present, creating an art installation of winter scenes, snow, and a nice blanket in the middle of it. Serena has been a person for which things come easy, but being with Dan inspires her to work more for their relationship. She really wants to make him happy and to share parts of herself with him. Initially, her relationship with Dan seems to be one of the healthiest that she's ever had. Of course, it changes and becomes more complicated, but at first it is sweet.
1 Nate: Is the Male Serena
While Nate may not be as bright as Serena, he does share a lot of her attributes apart from being extremely good-looking. Nate dates those not of his income class, too. He doesn't really care about neighborhoods or wealth. He's willing to get to know people, and he's open-minded. Although he can be more serious than Serena, he cares about people just as she does. In addition, he's willing to change and grow, too.
We can understand if Serena wouldn't want to date the male version of herself, but sometimes it would make sense if she dated Nate more than casually. In the show, Serena loved Dan above everyone else, still we wonder if he was the best for her or if Nate would have been better. Perhaps, another character she hadn't met yet would have been better than both of them.