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The 20 best things that happened on Gossip Girl
The CW Television Network

The 20 best things that happened on Gossip Girl

There may not have been a show that took as many wild twists and turns on The CW as Gossip Girl did. It also was a series that helped launch the careers of Penn Badgley and Blake Lively. When watching Gossip Girl, it was impossible not to see what was happening with these teenagers and eventual 20-something-year-olds and think how fabulous that lifestyle would be. Gossip Girl was ahead of its time when it came out, and for that, it remains a show that is just as rewatchable now as it was when it first came out. 

 
1 of 20

Kristin Bell’s Narration

Kristin Bell’s Narration
The CW Television Network

Her voice can still be heard to this day by any fan of this show. Her narration was timely and clever, and she always delivered a bit of snark, which gave each episode and each Gossip Girl blast exactly what it needed. There are a lot of iconic moments on this show, but the “XOXO” that was voiced by Bell remains atop the list.

 
2 of 20

Rufus and Lily

Rufus and Lily
The CW Television Network

These two had a bond that went back well before the show first began. Seeing the love they had for one another in the past created a touching journey, one that saw them get back together at one point. Things were a little weird when they were together at the same time their kids were, which ultimately made things weird for them, too. 

 
3 of 20

The Met Steps

The Met Steps
The CW Television Network

Their iconic for a reason. Every step needs it queen and Gossip Girl delivered with this backdrop. The Met Steps weren't just a work of art, they served to show the hierarchy of society within the walls of Constance St. Jude's. 

 
4 of 20

Nathan's Stand Against His Father

Nathan's Stand Against His Father
The CW Television Network

This was a tough one to watch but it laid the groundwork for Nate's arc as well as the redemption story that his father would undergo. It's never a good thing when it comes to blows between a father and son but that's what had to happen when Howard Archibald put the blames of his cocaine on his son. Nate turned him into the police after his father punched him, which ended up getting his father to realize how far he had gone in his downfall. 

 
5 of 20

Chuck and Blair’s Paris Moment

Chuck and Blair’s Paris Moment
The CW Television Network

The "Double Identity" episode finally reunites Blair with a much different Chuck, who was brought back to health after being shot in Prague. This is the episode where Blair learned that Chuck was intending on proposing to her before the incident, to which Blair goes and finds him at the train station to stop him from leaving Paris and to return to New York. 

 
6 of 20

Dan and Serena’s First Date

Dan and Serena’s First Date
The CW Television Network

They were opposites in every way imaginable in this world. That didn't stop Dan from pining for Serena's attention, so when he finally gets that date with her, a huge sense of relief was lifted off of his shoulders. Of course, that meant he would actually have to come up with something that would impress her (or so he thought) which led to Dan realizing that she didn't need a fancy dinner, just some quality time meeting his Dad and having to rescue his sister from the ugly grip of Chuck Bass. 

 
7 of 20

Lily Finally Appreciates Dan

Lily Finally Appreciates Dan
The CW Television Network

There was a moment in the 10th episode of Season 1 where Serena realizes her grandmother has been lying to her. Lily had already known her mother to be deceitful, so there was a whole chain of lying going on. Lily realizes that Dan is actually the one for her daughter in this moment, giving him a call to come fight for her at the cotillion. A memorable exchange occurs between the two as Lily opposes him dating his daughter, with her telling him she knows what her daughter has become since she met him and that "she returns home every night at a reasonable hour." 

 
8 of 20

The Thanksgiving Episodes

The Thanksgiving Episodes
The CW Television Network

Every show has its usual holiday that it owns. For example, Modern Family had a tremendous run with its Halloween episodes (and Valentine's Day). For Gossip Girl, it was Thanksgiving. These episodes were always juicy. There were five of them in total, with the Season 1 remaining its best. That was when Dan and Serena learned their parents had a history. Rufus had actually begun to get back with his ex-wife despite leading Lily on again, and it culminates in some touching family scenes to close it out. 

 
9 of 20

Dan’s Reveal

Dan’s Reveal
The CW Television Network

The biggest question of this entire series was always who the person was behind Gossip Girl. As we came to learn in the end, it was Dan Humphrey all along. The first episode even hinted at this by showing him on his bed with a laptop in front of him as the narration began. Still, it was never known until the end. While Dan was the one behind the operation, as he told everyone, Gossip Girl wasn't just one person, it was all of them since they all provided tips, photos and information to "her" over the years. 

 
10 of 20

Nate’s Newspaper Gig

Nate’s Newspaper Gig
The CW Television Network

Nate had a lot going on for him, but he was always hit with some major roadblocks that seemed to keep him off course. He eventually landed on his feet as the head of a digital newspaper, The Spectator. This was the outlet that eventually revealed Gossip Girl's identity and became a major player in the media landscape as was shown in the five-year time jump. Good job, Nate! 

 
11 of 20

Blair Being a Boss

Blair Being a Boss
The CW Television Network

Blair Waldorf is an iconic character. She was someone who had it all, then lost it and got it back. This was a character who very easily could have been unlikeable, and sometimes she was meant to be so, but the way in which Leighton Meester portrayed her gave her so much to offer that she couldn't help but steal every scene she was in. She's a Queen Bee for a reason. 

 
12 of 20

Blair and Dan’s Brief Fling

Blair and Dan’s Brief Fling
The CW Television Network

When a show is on long enough, strange relationships and hookups are bound to happen. No one saw Dan and Blair getting together but it did and it actually wasn't that bad. It was brief, but there actually was something there... it turns out that it was just a friendship. That being said, it still is amazing these two reached the point of actually like one another after so staunchly dismissing one another in Season 1. 

 
13 of 20

The Wild Brunch Episode

The Wild Brunch Episode
The CW Television Network

The second episode of Gossip Girl set the tone for what was to come. Serena invited Dan to his first real Upper East Side event, which was drama-filled. This is where fans get the first look at the love triangle between Dan, Nate, and Serena. another punch by Dan to the face of Chuck, the messiness of a Blair and Chuck plan comes to light and Dan learns that Lily and Bart have something going on. All of these things come into play throughout the show's run. 

 
14 of 20

Hillary Duff’s Character

Hillary Duff’s Character
The CW Television Network

She played a famous actress, Olivia Burke, who attended the same college as Dan and Vanessa, becoming a roommate with the latter. Olivia gets involved romantically with Dan and befriends Vanessa. Things get weird as Dan deals with dating a celebrity. The bizarre part is when the three of them engage in a threesome as part of Olivia heading overseas for a movie, which is conveniently canceled. The three are never the same after that as the relationship is called off. 

 
15 of 20

The Show Being Ahead of its Time

The Show Being Ahead of its Time
The CW Television Network

Gossip Girl was released in 2007. Twitter came out the year but took a few years before it really hit the mainstream. The idea of someone running a website and a notification system that would signal phones truly wasn't a major part of society like it is today when this show came out. It's pretty remarkable seeing this show’s foresight into what would become a pretty common thing down the road.

 
16 of 20

Bart’s Story Arc

Bart’s Story Arc
The CW Television Network

Who doesn't love a fake death? Chuck's father, Bart, is one of the more powerful men in New York City. He is seen in a relationship with Lily before eventually proposing to her. A Season 2 car crash is where he meets his demise... until Season 5. That's when he reappears, alive and well, with Diana Payne, whom Nate had been dating and working with. Bart faked his death to keep his family safe. 

 
17 of 20

The Messiness of Ivy

The Messiness of Ivy
The CW Television Network

Ivy, Charlie, Ivy? Whatever her name is, this was an extremely calculated character. Ivy first appeared as Charlie after being hired by Carol Rhodes to be her daughter and access her trust fund. She ends up taking the money for herself before being caught, and it's revealed her name is actually Ivy. Despite all of this, she remains in the picture, eventually dating Rufus and William as she makes the rounds through Lily's exes. Ivy was truly a messy character and one that was only written for the show and not included in the book. 

 
18 of 20

Dan and Serena Getting Married

Dan and Serena Getting Married
The CW Television Network

This is how it had to happen, right? Dan and Serena were always the end goal. There was always a back-and-forth between these two and untimely breakups that never lined up. Eventually in Season 6, they said this is our last shot and it's shown in the five-year time jump that they do, indeed, marry. 

 
19 of 20

Georgina’s Chaotic Schemes

Georgina’s Chaotic Schemes
The CW Television Network

Georgina has to be the most controversial character on this show, which says something. Her storylines were all over the place, from being a born-again Christian, telling Dan that she's pregnant with his son (which we later learn that Milo is not his son), and eventually taking over as Gossip Girl. She even was one of the few OG characters to return in the short-lived HBO reboot. 

 
20 of 20

Brittany Snow’s Episode

Brittany Snow’s Episode
The CW Television Network

There was only one episode that starred Snow but it was an important one for the character development of Lily. The Season 2 episode showed a young Lily in California who was kicked out of boarding school and has her own troubles to deal with, including a rebellious sister. The whole point was to show a comparison between her and her daughter, Serena. 

Kyle Phillippi

Kyle is a freelance writer who spent many years covering Philadelphia sports before honing in on the world of entertainment. Kyle's bylines include The Philadelphia Inquirer, SI.com, Metro, NBC Sports and more recently, Collider. Kyle can be found on Twitter, @Kyle_Phillippi.

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