Gossip Girl: The 5 Best Friendships (& The 5 Worst) | ScreenRant – Screen Rant

Gossip Girl is notorious for teenage drama, scheming, and the ups and downs of life on the Upper East Side of Manhattan. Throughout the six seasons of the show, characters naturally drifted away from one another and fell back together as the drama proceeded.

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Following the likes of Serena van der Woodsen and Blair Waldorf around New York City is nothing short of exciting, but there are some duos from the show that weren’t always as fun to watch. As the show added more characters, some amazing and odd friendships blossomed. Certain character’s friendships are totally iconic, while some are just plain strange. Here are the five best and worst friendships from Gossip Girl.

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10 Best: Nate Archibald & Chuck Bass

Nate and Chuck have their ups and downs like any friendship. The fact that someone as calm as Nate can be such good friends with somebody as intense as Chuck is – honestly – surprising. Although things got rocky when Chuck started making passes at Nate’s then-girlfriend, Blair, they made it through as any strong friendship should.

Through girls, college, and business deals; this pair was always there for each other in a way that one could only describe as brotherly. They are both flawed guys, but their opposing personalities truly bring out the very best in each other.

9 Worst: Juliet Sharp & Vanessa Abrams

Talk about one of the evilest duos in Gossip Girl history. Even though deep down Vanessa was a good person, the fact that she even teamed up with Juliet in the first place is crazy. Juliet’s mission in life was to take down Serena, regardless of who she destroyed along the way.

After such a long time of Dan not choosing her over his new group of friends, Vanessa finally had enough and decided to join forces with Juliet to take down the Upper East Side snobs.


8 Best: Eric van der Woodsen & Jenny Humphrey

Before Jenny got totally sneaky, her friendship with Serena’s little brother Eric was really sweet. They leaned on one another as they attempted to navigate the rules of high school royalty, and gave each other sound advice as they grew up among the craziness that is their two families.

7 Worst: Serena van der Woodsen & Georgina Sparks

What started as harmless high school fun, quickly warped into the most destructive friendship on Gossip Girl. Not only was Georgina Sparks just plain mean, but she was also manipulative and scary. She understood Serena’s thought process and knew exactly how to play mind games on her.

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Serena was close to Georgina when she was young and in a phase of constant partying and drinking, but this toxic relationship paired with Serena’s terrible judgment at the time only produced horrible situations for this pair.


6 Best: Dan Humphrey & Nate Archibald

Dan never really fit into the world of Nate Archibald, but even in the early seasons when everyone else was so against Dan, there was a glimmer of positivity from Nate. In those times when Nate shut out the world, somehow Dan could relate and help him out of whatever dark place Nate found himself in.

They both could somehow relate to not completely fitting into the worlds they were thrown into, and they had each other to seek out in times of drama.

5 Worst: Dan Humphrey & Blair Waldorf

There wasn’t anything necessarily terrible about this pair, but it just felt like they never fit together. Whether they were strictly friends or locked in a weird and secretive romance, this pairing felt forced.

Deep down, they both knew they were truly too different to ever make anything work. It was good that they had their time together without Blair totally degrading Dan (she barely ever called him by his first name) but it kind of felt like two puzzles pieces that just did not go together.


4 Best: Serena van der Woodsen & Blair Waldorf

The most iconic friendship in Gossip Girl history goes to these two. Serena and Blair had the type of friendship that people aspire to find. Despite occasionally trying to sabotage each other, deep down Serena and Blair shared a mutual love that always brought them back together.

Regardless of the ways they tried to hurt each other, you always knew they would be back together again ruling the halls of Constance, as well as the rest of Manhattan. Every other character envied these two because they couldn’t be them…S and B forever!

3 Worst: Jenny Humphrey & Agnes Andrews

Poor little J could never catch a break. When she tried to make it on her own as a designer alongside model friend Agnes, things went south fast. Agnes was irresponsible and carefree, but Jenny had her entire future riding on her shoulders.

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At first, it was a fun friendship that allowed Jenny to chill out a bit. Unfortunately, she quickly realized that all Agnes brought into her life was trouble. She never took their business partnership seriously, burned Jenny’s designs, and drugged her at a fashion show. It’s safe to say that this relationship was extremely toxic.


2 Best: Blair Waldorf & Dorota Kishlovsky

This friendship was more of a mother/daughter relationship than anything. Although Dorota technically worked for Blair, she never failed to stand up for her, be her shoulder to cry on, or be the first one to buy her macarons when she was upset.

Dorota played the role of mom while Mrs. Waldorf was jetting off to Paris. Dorota knew all of the teenage drama, and many people thought she was the person behind the ‘Gossip Girl’ website. Blair just confided in Dorota about everything. Dorota was her right-hand man, so to speak, and Blair supported her right back.

1 Worst: Rufus Humphrey & Ivy Dickens

Ivy was really just the worst. She took advantage of nearly everyone in the Van der Woodsen/Humphrey family. Nobody really understood how Rufus could fall for her games, but he sadly did.

Ivy was definitely good at manipulating Rufus’ feelings, we will give her that much. Nothing is worse than the way she played Rufus and his kind heart. Luckily, Ivy got hers when William van der Woodsen completely fooled her into thinking he was on her side.

NEXT: Every Major Gossip Girl Couple, Ranked


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