Top 10 Gossip Girl Moments
The best of the best Gossip Girl moments will just leave you wanting more.
These were the moments that had viewers everywhere yelling three letters: O-M-G! Join MsMojo as we count down our picks for "Top 10 Gossip Girl Moments."
For this list, we’re looking at the biggest shockers, cliffhangers, and sexy hookups of the hit teen drama. We’ll be heading into some spoiler territory here, as the fates of a few characters are revealed on this list– so, spoiler alert!
Kicking off our list, we have the moment that started it all. The first episode begins with Serena returning to Manhattan after disappearing for a year to boarding school. She didn’t tell anyone why she left, although we soon find out that she had a pretty good reason. When Blair, her best friend, decides she’s ready to take the next step in her relationship with her boyfriend Nate, he reveals to her that during a wedding last year, he cheated on her with Serena. It’s the confession that spiraled the tense, up-and-down “frenemy” relationship between the two girls; although, they manage to work things out by the end of the series.
Ah, the beginning of the end of the mystery that opened Season Four. Juliet Sharp arrived on the scene innocently enough—or so it seemed. But we soon learned that she had an agenda of her own: Ruin the life of Serena van der Woodsen. It’s later revealed that Serena had a relationship with Juliet’s brother who ended up in jail, which Juliet is convinced is Serena’s fault. As part of an elaborate revenge scheme, Juliet Sharp, with the help of Jenny Humphrey, drugs Serena. She then places her in a taxi and sends her off to somewhere unknown, leaving Serena in a very dangerous position.
The first of several Chuck and Blair moments to appear on this list, this one came from the winter finale of Season Five. Despite her engagement to a prince, whose baby she is also carrying, Blair cannot deny her eternal love for bad boy Chuck, so the two decide to run away together. However, they’re tailed by paparazzi following a Gossip Girl blast, leading to a car crash that cost the life of Blair’s unborn child, and left Chuck at death’s door. It was a heavy cliffhanger to leave us on during that very cold winter, to say the least.
Following his return from his fake death at the end of Season Five, Bart Bass wastes no time taking back his empire from his son, Chuck. Between scandals and even trying to have Chuck killed at one point, it all leads to a tense showdown on a rooftop. Father and son wind up in a brief scuffle that ends with Bart hanging by his son’s arm over the ledge of a building, with Blair arriving just in time to see Bart fall to his definite demise. Quite the set up for the series finale… and Bart, try to stay dead this time, okay?
By Season Four, it was one of the few pairings on the show that hadn’t been explored yet. Blair and Dan didn’t have many positive interactions since the start of the series; however, as time went by, things started to lighten up between the two, resulting in a genuine friendship. But come on, you can’t just be friends on Gossip Girl for long. Those pesky feelings eventually pop up, and, strangely enough, they were mutual. Even if it didn’t last very long, the first kiss between Blair Waldorf and Dan Humphrey was one for the ages, and had the fan base flipping out.
Ever since the beginning of the series, Blair and Chuck have a bond that rivals the show’s core friendship of Blair and Serena. At the end of the second season, Blair ups the game a bit by telling Chuck she loves him, and asks him to reciprocate those three special words. When Chuck finds himself unable to, Blair backs off, breaking the hearts of viewers. But don’t worry—Chuck more than makes up for it by the end of the episode, when after a brief tour of Europe, he returns to Blair with some of her favorite presents. He finally tells her those three big words, beginning their long-awaited relationship. It was about time.
If Season Two’s ending of Blair and Chuck’s blossoming romance was a happy ending, the end of Season Three was a tragedy. Believing he has lost Blair for good, a depressed Chuck ends up sleeping with Jenny Humphrey. Once this bombshell drops, Chuck gets punched by Dan and exiled by Blair. Heartbroken, we find Chuck stumbling through Prague. Robbed at gunpoint, Chuck refuses to give up an engagement ring meant for Blair. The final moments of the season show Chuck getting shot and left to die in a pool of his own blood. They really wouldn’t kill Chuck off… would they?
Georgina Sparks is a real piece of work, and one of the many recurring antagonists on the show. A master schemer, she causes plenty of damage to the lives of the core Upper East Siders. So how could she get any more despicable? Well, when Dan was ready to follow Serena to Paris to try and work things out, he gets a surprise visitor. That’s right: Georgina was at his door, AND she was very much pregnant. Oh, and the child could very well have been Dan’s, although we later find out he wasn’t. Seriously, Dan, a one night stand with the enemy really did prove to be your biggest mistake.
It was the question we asked since Episode One. Who was the anonymous, faceless blogger who was both a secret friend and the greatest enemy to the Upper East Side cast? Following a montage of reactions, including one from the voice of Gossip Girl herself, Kristen Bell, the final curtain was drawn back. Did anyone ever expect Dan Humphrey of all people to be the one and only GG? We sure didn’t. This could have been an entire episode in and of itself, walking us through all of Dan’s exploits throughout the series. Still, it was one of the best final gifts from our favorite series.
Before we unveil our top pick, here are some scandalous honorable mentions:
- Dan's Threesome with Vanessa and Olivia—“The Last Days of the Disco Stick”
- The Final Scene—“New York, I Love You XOXO”
- Serena's Confession—“Woman on the Verge”
- Serena and Blair's Catfight—“New Haven Can Wait”
- The Dance Number of the 100th Episode—“G.G”
It is fitting that the beginning of Chuck and Blair’s romance takes the top spot of our list. After a disastrous night with her then boyfriend, Nate, Blair finds her way to Chuck’s burlesque club, where she accepts a dare to dance on stage. The sight of a gorgeous Blair enjoying herself is enough to make anyone fall for her, especially Chuck. It’s no wonder that, on the ride home in Chuck’s limo, the two finally give into their passions and the obvious heat between them. It was the beginning of the longest and most beloved romance of all of Gossip Girl.
Do you agree with our list? Which moments had you calling or texting friends in excitement and shock? For more jaw-dropping Top 10s published daily, be sure to subscribe to MsMojo.