Romance is an integral part of Gossip Girl. However, the show is far from an example of healthy, loving relationships. What makes the series so entertaining is how awful everyone behaves towards each other.
Healthy relationships on Gossip Girl are rare since they're mostly motivated by greed. Even many of the best couples on the show have cheated, lied, and used each other. After all, what's love without a little drama?
Lily And Rufus
Lily and Rufus had plenty of ups and downs throughout their relationship. They were each other's first love, and never really got over one another, despite multiple marriages in between their reunion. They try to move on from one another with other people. They finally decide to embark on a relationship and get married in season three. Though they constantly fight and almost never see eye to eye, they love each other and make each other happy.
When it's revealed that Bart is still alive, Lily has to choose which marriage she wants to annul. Tired of all the fighting, she ends things with Rufus and gets back together with Bart. Rufus and Lily's separation brings out the worst in each of them, as Lily turns into a stone-cold monster and Rufus enters a relationship with a young woman he once thought was his niece.
Dan And Vanessa
Dan and Vanessa make a lot of sense if you're into the whole "date your best friend" thing. They're both supposedly "poor", even though Dan lives in an enormous loft in Brooklyn. They're both sort of pretentious and really enjoy judging other people. They look down their noses at the kids from the Upper East Side, and yet won't stop trying to get "in".
It really would have saved them and everyone else a lot of trouble if they would have stayed together and stayed out of all of the drama. Unfortunately for Vanessa, Dan's obsession with Serena gets in the way of their relationship when he cheats on her with Serena, and Vanessa engages in some deception of her own as well.
Blair And Dan
Few would believe that Dan and Blair would have ever been a couple based on their interactions in the first three seasons of Gossip Girl. They disliked each other from the start, and Dan was dating Blair's best friend, Serena. They eventually formed a sweet friendship when they intern for the same magazine, and Dan sees that Blair is actually a more decent person than he'd realized.
They also bond over their shared love for old movies, and Dan begins to realize that his feelings for Blair are deeper than friendship, though she doesn't return them. By sticking by her side throughout all of her drama with Chuck and Louis, Dan is able to win Blair over, and the two enter into a sweet relationship. If it weren't for Blair's connection with Chuck, the two would have made a good match.
Chuck And Raina
When Chuck and Raina first meet, Chuck finds that he's met his match. Both come from high-powered businessmen for fathers, and each have a very laid-back, no-strings-attached approach to sex. At first, their relationship is very casual, but Chuck thinks that he can save his company from Raina's father if he can make her fall for him. In the process of wooing Raina, Chuck finds that he really does care about her.
Just as it appears as though their relationship could be the real thing, Raina discovers Chuck's nasty habit of putting business over family and breaks things off.
Eric And Jonathan
Eric and Jonathan are mostly background characters, but the two seem to have a sweet, drama-free relationship (at least when Jenny isn't bullying them). Jonathan is the first guy Eric really gets serious with, and they're together for a while before things go south. Eric tires of Jenny's rudeness and decides to start fighting back.
He sabotages her cotillion, and things continue to escalate and become increasingly nasty. Jonathan finds this side of Eric unattractive and breaks things off.
Chuck And Eva
When Chuck is robbed and shot in Prague, Eva finds him nearly dead and lying in the street. She saves his life, and he lies to her about who he is. After losing Blair, Chuck wants to leave his old life behind and wants to be a better person with Eva. When Blair finds him and asks him to come back, he and Eva return to New York.
Chuck tries to follow Eva's charitable influence, but he can't resist Blair's schemes and ultimately ruins his relationship by refusing to trust Eva.
Nate And Vanessa
Nate and Vanessa were a surprisingly sweet couple, even if they were a little dull. They might not have much drama, but this adds to the charm of this pairing. When they're still in high school, Nate is obsessed with being different from his parents, and Vanessa represents something outside of the Ivy League, trust-fund type his family would choose for him.
Nate and Vanessa are two of the kinder characters on the show, and they have a genuine affection for one another until Vanessa falls into scheming herself.
Carter And Serena
Carter and Serena start spending time together when he starts helping her track down her father. They spend the summer trotting the globe, searching for William and develop feelings for each other. Serena avoids Carter, preferring to stay in denial about her father's indifference towards her, but he makes her face the truth. Carter and Serena share a few things in common: they each have a wild past, and they both spend most of their time telling other people how much they've changed while continuously getting into trouble.
Carter really does stay faithful to Serena, but when old debts come back to haunt him, they disagree on how to handle the situation. Serena uses deception to try to get him out of the sticky situation, but Carter prefers to face his issues head on, and leaves Serena brokenhearted.
Blair And Chuck
Chuck and Blair have the most in common out of any of the couples on the show. The two love scheming and are willing to go to great lengths to get what they want. Chuck's promiscuity allows Blair to let go of her perfect image, and the two have a lot of fun together. It takes a while for Chuck to be mature enough to be in a relationship, but his feelings for Blair force him to grow up and face his feelings.
The two have a relationship that works well for them until Chuck's greed ruins everything. He never stops loving Blair, even when she's engaged to Louis and dating Dan. After seeing how much he's grown, Blair is ready to be with Chuck again. They settle what they need to in their careers and finally get married in a truly dramatic fashion.
Cyrus And Eleanor
Cyrus and Eleanor are the healthiest couple on the show. In fact, the only squabble they appear to have is when Cyrus fails to tell Eleanor he cheated on his first wife. Cyrus is a lovely and kind person who makes Eleanor happy and brings a good dose of light-hearted fun to the Waldorf family.
They remain unproblematic and removed from most of the drama, and Cyrus' worst quality is having Aaron for a nephew.