Gossip Girl: The Best (& Worst) Trait Of Each Main Character

The beauty of following the characters on Gossip Girl was that just when you invested in liking (or hating) each of them, a situation would arise and their behaviors would have you switching sides.

We’d love Blair or Chuck when they were showing their softer more vulnerable sides, then she’d turn around and throw Serena under the bus, or Chuck would pick a fight with Dan and embarrass him at a highfalutin social affair, and we’d throw our collective hands up. Or we’d cheer for Serena or Nate getting their acts together, and out of nowhere she’d be sleeping with her professor or Nate’s married cousin, and he’d be bedding a high school girl. But good, bad, or ugly, we tuned in anyway.

10 Georgina: Engaging (But Deceitful)

Georgina (Michelle Trachtenberg) engages the others with passive/aggressive behavior, sucking them in by being accommodating, caring, and a good listener.

On the other hand, if pot-stirring were an Olympic event, Georgina would take the gold. How low would she go? She slips Serena drugs so the high society blonde missed the SATs, outs Eric (Connor Paolo) as gay, manipulates a way to be Blair’s roomie at NYU, and gets pregnant and convinces Dan that son Milo is his.

9 Vanessa: Down-To-Earth (But Insecure)

Dan’s childhood friend and a budding filmmaker, Vanessa (Jessica Szohr), is grounded in a way that the Upper East Side set is not. She believes in Dan’s writing and submits his story to “The New Yorker,” hence is responsible for him getting published. She managed to hold her own with Blair & Co. by remaining true to herself.

But, it’s always clear to Vanessa that she’s an outsider when not dressed fancy enough for Blair’s 17th birthday party, competing for a college internship against those with connections, and made to be the subject of ridicule as when Jenny offers her an unlined dress for the Snowflake Ball, which exposes her silhouette when she stands in the light.

8 Jenny: Creative (But Desperate)

“Little J,” as she’s also known, is a talented fashion designer garnering an internship with Blair’s mother at Waldorf Designs. Jenny (Taylor Momsen) is very sweet and a good friend to Eric.

However, she is desperate to be part of the Upper East Side world of money, glamour, and sophistication – three things not innate to her upbringing – so she compromises herself by doing Blair’s bidding, stealing an expensive dress while at a sleepover, and, after Blair graduates from Constance Billard, taking her place on the steps of The Met complete with a headband.

7 Rufus: Free-spirited (But Self-Conscious)

Once the frontman for Lincoln Hawk, Rufus (Matthew Settle) now runs an art gallery and takes care of Jenny and Dan as a single dad. He tends to see the best in others, but when it comes to his children is very protective, like when he took on Georgina and made his son get a paternity test. He sends his kids to Manhattan for school because he wants what’s best for them.

That being said, Rufus still carries a torch for one-time groupie/muse Lily and the feeling is mutual. They marry, but the fighting and eventual divorce comes about because the now-socialite was not about to leave her penthouse for The BK. Living in Lily’s world only diminishes the salt-of-the-earth guy who cannot compete with the money and power.

6 Lily: Sophisticated (But Snobbish)

The multi-married Lily (Kelly Rutherford) is an Upper East Side doyenne with moey and influence and uses both mostly to keep her children out of trouble. She has a big heart, which she opened to motherless Chuck during and after she was married to Bart Bass.

Lily may be kind to “the little people” in a noblesse oblige way, but is merciless when crossed. When Serena was in boarding school and (untrue) rumors flew that she was having an affair with a teacher, Lily had him thrown in jail; the consequences being his sister, Juliet Sharp (Katie Cassidy), showed up to enact revenge.

5 Chuck: Generous (But Angry)

Chuck (Ed Westwick) is a hotel scion who grew up without a mother and with a disaffected father. His hard shell envelops a heart that wants to give and get love. His goodness comes out when friends are in trouble, such as when Blair’s family would have gone broke paying her dowry to end her sham marriage to Prince Louis of Monaco. Chuck footed the bill.

Nevertheless, this cool bad boy can turn into a genuinely bad guy taking mean to the nadir, such as when he almost succeeded in sexually assaulting Jenny.

4 Nate: Charming (But Disheartened)

“To All The Girls I’ve Loved Before” could be the theme song of this member of the Vanderbilt family (on his mother’s side). No one is safe from his charisma as the heir has courted Serena, Blair, Jenny, and Vanessa from the core UES squad, Juliet Sharp, his married Hamptons neighbor Duchess Catherine Beaton (Mädchen Amick), his boss Diana Payne (Elizabeth Hurley), and on the other end of the spectrum, 17-year-old Sage (Sofia Black D’Elia).

When Nate’s criminal dad, Howard Archibald, flees the country and his mother moves from Manhattan in shame, the one-time golden boy is left with no money and an empty townhouse. He eventually gets back on his feet, only to realize his grandfather and politician cousin Tripp are dishonest.

3 Dan: Good-Natured (But Duplicitous)

Dan (Penn Badgley) is totally out of his league with the UES crowd, but because he lacks the swagger of the male scions at St. Judes, the budding author attracts the attention and affection of Serena, who needs a bit of normal infused into her chaotic life. Eventually, easy-going Dan is embraced by the group.

For all his “aw shucks I’m the cater waiter serving my friends at one of their penthouse parties” demeanor, Dan not only writes a book exposing the private lives of his friends, but it is revealed that he is indeed Gossip Girl, who has been telling their secrets, hence making trouble for them, all along.

2 Blair: Trendsetter (But Elitist)

If everyone on Manhattan’s Upper East Side is wearing a headband, Blair Waldorf (Leighton Meester) is who to thank. She held court on the steps of The Met with mini-me minions doing her bidding, planning parties to which everyone wanted an invite. When there was a caper to be carried out, Blair took the reins and masterminded the agenda. She saw herself as a princess and had two royal love affairs, but ended up with an heir to a fortune.

Blair’s competitiveness can only be bested by her snobbery. For a lot of the series, she treated Dan (who she called Humphrey) like dirt because he hailed from an outer borough. The mean girl thing extended to Jenny, whom she tolerated long enough to take advantage of, and called Serena her BFF, yet was so jealous of her that Blair was always willing to sell her out, as in when she told Sage she’d break up her dad Steven and Serena if the teen would wear a Waldorf Design dress to cotillion.

1 Serena: Bohemian (But Self-Destructive)

The stunning and independent It Girl may have been part of the UES crowd, but always stood out in it. From her effortless-chic take on her high school uniform (that would have gotten anyone else a detention slip for slovenliness) to flowing gowns or micro-mini cocktail dresses she wore to society events, when Serena walked in all eyes were on her. Unlike Blair, Serena didn’t want to be copied; she enjoyed the cachet of being one-of-a-kind.

“Beautiful things grow to a certain height and then they fail and fade off.” Serena quoted from F. Scott Fitzgerald’s The Beautiful and Damned to a movie director after a chance encounter with his assistant who was reading the book. “I relate to it more than I should admit,” she added before he offered her a  production assistant position. For all her good fortune, Serena often feels worthless and not taken seriously, so she acts out with men and was known to abuse substances.