Summary

• Rewatch Gossip Girl for iconic drama, witty quotes, and Upper East Side scandals.
• Streaming services make binge-watching easy, relive all the best moments now.
• Memorable quotes showcase drama, relationships, and character growth on the show.

Gossip Girl is one of the most rewatchable teen dramas in recent memory with some snappy Gossip Girl quotes that certainly stick in the mind. The original series, inspired by a series of novels, follows a group of teenagers who live a privileged and dramatic life on the Upper East Side, but have their every move watched and blogged about by the mysterious Gossip Girl.

Thankfully, streaming services have made rewatches possible and fans can easily binge all of their favorite episodes. Now is a great time to relive all the best Upper East Side moments. The best Gossip Girl quotes are as funny, smart, and dramatic as the tone of the series. From the Gossip Girl sign-off to funny Gossip Girl quotes about Blair scheming or Dan being the one behind all the messages, there are definitely countless quotes that are entertaining and fan-favorites.

“Whoever Said Money Doesn’t Buy Happiness Doesn’t Know Where To Shop.”

Blair - Season 1, Episode 16 “All About My Brother”

In the first season of Gossip Girl, Blair and her friends are seen as superficial by outsiders. This particular line might seem like it plays into that, but there is more to it than simply Blair being superficial.

Though Blair grows a lot as a friend and a person in general throughout Gossip Girl, one thing that remains consistent about her character is using things she loves to allow herself a break from the drama in her life. She loves pastries from Paris, classic movies, lavish parties, and shopping for the latest fashions.

That’s best exemplified in this season 1 quote from Blair. While the old adage “money can’t buy happiness” is often thrown around, it’s undeniable that money can give someone access to activities that can help them feel better, if not happy, as well. Blair understands that idea, even if this line is thrown out for laughs.

“... On The Upper East Side, We All Know Love Is Pain.”

Gossip Girl - Season 3, Episode 5 “Rufus Getting Married”

While some viewers might have tuned into Gossip Girl for the backstabbing, and others might have tuned in to try to figure out the identity of the title character, more often than not, the real entertainment in the show is the relationships. The relationships - both romantic and platonic - are the driving force behind the show and its storylines. Even narrator Gossip Girl knows that, which prompts this quote from her in season 3:

Some say love is a river, some says love’s a silly song. Some say love is all around us. It lifts us up where we belong. Some say love is hearing laughter in the rain. But on the Upper East Side, we all know love is pain.

One of the things that becomes evident in the series is that the people the characters love the most are the ones able to hurt them the most. The audience sees that time and again with the conflicts between Chuch and Blair, Serena and Dan, and even Blair and Serena. Their love comes with a whole lot of pain as they all repeatedly hurt one another, go their separate ways, and then come back together. Ultimately, their pain is worth it as they all get their happy endings.

“I Look Forward To Never Seeing You Again.”

Blair - Season 4, Episode 6

Blair isn’t shy when it comes to people she considers her enemies. While she, like anyone raised on the Upper East Side, can display social niceties when prompted, even toward people she doesn’t like, she doesn’t often feel the need to pretend. That means if she doesn’t like someone or doesn’t trust someone, they know it. That’s certainly true when things come to a head between her and Jenny Humphrey.

Jenny, after being banished from her hometown, returns for a fashion competition. Even though Blair gives Jenny her permission to be back in town for this one thing, Blair doesn’t just let bygones be bygones. It’s Blair at her worst as she digs into her hatred of Jenny. This line isn’t one of Blair’s best insults in the show, but it demonstrates just how hard she hangs onto a grudge. Blair can’t help but see Jenny off by reminding her that she never wants to see her again.

"Looks Like Blair And Chuck Showed Up With Quite An Appetite — For Destruction That Is."

Gossip Girl - Season 1, Episode 2 "The Wild Brunch"

While there are many fabulous events on Gossip Girl, season 1's brunch is one of the best since it's when Serena and Blair's tricky friendship shows its real complexities. Now that they're part of the same friend circle again after so much time apart, it's not easy for either of them. Blair also has to deal with hiding her feelings for Chuck. While many of Gossip Girl's quotes are fun, this is one of the most compelling since it explains exactly who Chuck and Blair are: schemers who always come out on top.

This particular line appearing so early in the show demonstrates that Gossip Girl, anonymous at the time, knows exactly how Blair and Chuck operate despite not being a member of their inner circle - yet. It's a great indicator that, even though Blair maintains a good-girl image and is very particular, others know that she rules her school with an iron fist.

“I Tried To Warn You. There's A Price To Pay. I Always Knew A Girl Like You Couldn't Afford It.”

Blair - Season 1, Episode 16 “All About My Brother”

In the first season of Gossip Girl, Jenny Humphrey manages to make an enemy of Blair Waldorf. Jenny initially idolizes Blair for her sense of style and the respect she commands from other students. Blair, however, points out early on that she doesn’t believe Jenny has what it takes to be the Queen Bee, and when Jenny eventually agrees, Blair gives this memorable Gossip Girl quote.

While Blair’s line is more of a dig at the Humphreys not having as much money as the families that make up Blair’s inner circle of friends, it’s also in response to Jenny’s ission that she’s done things completely out of character for herself. Blair might look like she has everything together at all times, but her image is carefully cultivated and maintained, and as a result, not many people know the real Blair. That’s the price she pays.

“You Can't Be Worse Than The Guys I Do Know."

Serena - Season 1, Episode 1 “Pilot”

Long before Dan is revealed to be Gossip Girl, he’s just a classmate wanting Serena’s attention. When he decides to get up the courage to ask Serena out, and she surprises him by agreeing, he voices his additional surprise that she would be willing to go out with someone she doesn’t even know. Serena responds, “You can’t be worse than the guys I do know.”

Serena’s line is a little prophetic. After all, most of the guys that Serena knows are willing to lie, cheat, and steal to get what they want. They don’t care about who gets hurt along the way. While Dan takes on some of those traits as he becomes more embedded in her Upper East Side friend group, he’s not any better or any worse than most of the other guys she dates throughout the series - other than the reveal that he's really Gossip Girl in the end.

“You Two Have Some Strange Force Field Effect On Each Other. Physicists Should Study It.”

Dan - Season 5, Episode 19 “It Girl, Interrupted”

Though Dan and Blair become close for a while, the two ultimately decide to go their separate ways, and they end up with their previous partners - Serena and Chuck. Dan, however, isn’t oblivious to the pull between Blair and Chuck, and though he doesn’t exactly like Chuck, he has a lot of respect for Blair. When she and Chuck find themselves drawn to one another again in season five, he tells Blair this particular Gossip Girl quote.

This quote in particular resonates with fans because a lot of them weren’t expecting to be so drawn into the Blair and Chuck dynamic in the series. Their relationship is, arguably, a toxic one as they both use one another and treat other people horribly in their attempt to be loyal to one another. They do, however, both learn from their mistakes with one another and grow into better people by the end of the series as a result of their pull toward each other.

"Destiny Is For Losers. It's Just A Stupid Excuse To Wait For Things To Happen Instead Of Making Them Happen."

Blair - Season 3, Episode 19 “Dr. Estrangeloved”

Though Blair and her friends are born into a life of privilege that opens a lot of doors for them, Blair is not the type of person to just wait around for things to be handed to her. Instead, she is a big proponent of making things happen for herself. In some cases, that might just mean ordering her minions to do things for her, and in others, that might mean going after an internship that she thinks will open even more doors for her.

It also means that Blair doesn’t wait for her handsome prince to come to her. While she thinks there’s an element of living out a fairy tale when she meets Prince Louis, Blair doesn’t just wait for someone she thinks is worthy to find her. She seeks out relationships, both romantic and platonic, with those she believes are a good fit. Sometimes, she’s right, but other times, her instincts are wrong. That doesn’t mean she doesn’t keep trying.

“The Only Thing More Shocking Than The Truth Are The Lies People Tell To Cover It Up.”

Gossip Girl - Season 1, Episode 16 “All About My Brother”

Near the end of the first season of the show, Blair and Jenny officially become rivals as Jenny angles to become the next Queen Bee at school and tries to steal Blair’s minions out from under her. While that happens, Jenny also gets a boyfriend, who it is eventually revealed is seeing Serena’s younger brother behind Jenny’s back. The lie from Asher and the truth from Eric are what prompts this voiceover from Gossip Girl.

While it applies specifically to Jenny and Asher’s relationship in the show, it’s also an accurate way to describe quite a few of the twistiest storylines in the show. Lies upon lies are told by the characters to cover up how they really feel or something they’ve done in the past. This is only the tip of the iceberg in the first season.

“For People Like Us, A College Degree Is Just An Accessory.”

Chuck - Season 3, Episode 2 “The Freshman”

As is true with any television series aimed at teenagers, the senior year of high school for the Gossip Girl teens puts a large focus on getting into a good university to pursue higher education. Characters like Dan and Blair have lofty goals, while Serena and Nate struggle with figuring out what they want and what’s expected of them, but Chuck has his own ideas about going to college.

Chuck embraces his life of privilege more than most. He understands that the wealth and connections of his family are going to open doors to him that might not normally be open to him, even with a college degree. He doesn’t see the need for a college degree when he’s already been in the middle of the family business since his teen years. Chuck is open about not wanting to go to college, unlike the rest of his friends.