As most teen dramas do, Gossip Girl deals with its fair share of deep issues and controversial topics. The characters all reach rock bottom at one point in the series, and the atmosphere feels rather solemn at times. However, it's also one of the rare shows that manage to balance itself out.
Gossip Girl focuses on a group of spoiled students from the Upper East Side, who tend to overreact to minuscule issues. The means that they go to solve problems is often comedic, and the characters can make anything funny through the way they interact.
9 Dan & Blair Fight Over Their Internship
Dan and Blair had just started to realize that they enjoy each other's company when they both end up with the same internship at W Magazine. Blair needs to be the best at everything, but Dan knows Blair and how she operates.
Their entire first day is hilarious, and they take whatever opportunity they can to make the other look bad. A simple stapler starts a scuffle, and they end up in a free-for-all at the W Party. Dan and Blair both get fired when their boss catches them tussling on the ground. Anytime Blair and Dan share a scene, chaos is almost guaranteed to ensue.
8 Blair Steals Chuck's Shoes
Chuck and Blair's relationship didn't age well, but they had a fair share of funny moments when it comes to making viewers laugh. Even when they were a couple, the two were always trying to one-up each other. They were more competitive than supportive, and they both did whatever it took to win.
When Blair realizes that Chuck has been trying to distract her with sex to obtain the photograph they both want, Blair leaves to go get it herself. She grabs Chuck's shoes along with her own things, leaving Chuck in a state of confusion.
7 Georgina Is Found In An Unlikely Place
There's nothing wrong with celebrating a person's faith, but a camp that preached love and forgiveness was the last place Chuck expected to find Georgina. It was startling to see the most manipulative and unapologetic character on the show have such a massive change of heart.
Georgina had gone from selfish to selfless, and because viewers hadn't seen the transition, it was hard for everyone to wrap their heads around it. The Upper East Siders' reaction to the new Georgina was comical in itself.
6 The School Play Gets Personal
Constance's production of "The Age of Innocence" goes south when the characters get too caught up in their own issues. Dan and Blair argue during their performance, but continue to act in love, confusing the audience. Dan and Blair are one of the best duos in the series, and they could single-handily turn the show into a rom-com.
They weren't the only students diverting from the script, and Nate starts telling off the director during a big scene. It leads to everyone breaking character, which causes chaos to ensue. The funniest scenes in Gossip Girl always seem to happen in the midst of disaster.
5 A Group Of College Students Mistake Dan For Nate
The Archibald legacy was in tatters thanks to Howard, so Nate decided to be someone else for the day. He told everyone at Yale that his name was Dan Humphrey, unaware that he was putting a target on Dan's back. Nate is one of the few characters on the show who doesn't do things with malicious intent, and when he makes a mistake, he does whatever he can to make it right. A group of students mistake Dan for Nate and leave him tied to a statue in his boxers.
The act itself was more mean than funny, but the comedy comes from Dan's reaction. He attempts to get the attention of bypassers by yelling, "I know this is a strange request, but could you untie me?" Nate did comes to Dan's rescue and offer an apology, but he didn't miss the opportunity to poke fun at his friend. When the girl that Dan's crushing on comes toward them, Dan panics because he's not proud of his choice of boxers. Dan definitely learned to always be prepared when attending Yale.
4 Blair Walks In On Georgina & Dan
By the time Gossip Girl Season 3 rolled around, Blair and Dan were still enemies. In fact, one of the only people Blair hated more than Dan, ended up becoming her roommate at NYU. Blair ignores the sock on the door and enters her dorm, only to find Dan making out with Georgina on her bed.
Blair's reaction is comedy goal, and she acts as if her eyes need to be flushed with holy water. She screams "ew" repeatedly and throws things at Dan while he scrambles to button up his shirt. Georgina, on the other hand, is completely unfazed.
3 Chuck Traps Serena & Blair In The Elevator
Blair and Serena had their fair share of good and bad moments. There were times when they were friendship goals, but they would also backstab each other at every opportunity. It wasn't abnormal for them to end up in a fight, and they called things quits on more than one occasion.
Blair and Serena are so stubborn, that the only way to get them to make up is to physically lock them in a room together. Chuck takes it upon himself to trap Blair and Serena in the elevator, and their reaction is hilarious. However, the funniest part is when Chuck mentions that he stocked the elevator with macaroons to sustain them.
2 Georgina Locks Dorota In A Closet (With Snacks)
Surprisingly, Dorota is one of the funniest characters in Gossip Girl. She may work for Blair, but she has no problem chastising her and letting her know when she's making a mistake. Although it's a job, Dorota's loyalty to Blair has nothing to do with money. She genuinely loves her and treats her like family.
After her wedding takes a turn, Blair tries to flee the country to get an annulment. Georgina walks in on Dorota packing Blair's bag, but Dorota refuses to give up her location. Georgina locks Dorota in the closet out of revenge, but because she's now a mom, she makes sure to leave her with some snacks.
1 Blair & Dan Go To A Live Reading Of "Inside"
Blair was determined to prove to Serena that she didn't have feelings for Dan, but the number of great quotes they have suggests the opposite. To show that she isn't avoiding him, Blair seeks Dan out and finds him at the rehearsal of a live reading of his book. Blair and Dan bicker as normal, clearly trying to avoid what's going on between them.
Blair even offers to hold Dan's hand for support which he immediately rejects. She tends to do more harm than good, and a lot of the show's drama comes from how far Blair will go to prove a point. Blair kisses Dan to display how a Claire/Dylan kiss should be like "petting a dog," but it quickly turns real. One of the best moments of the episode is when they pull away and Blair scolds Dan for ruining the case in point.
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