The Worst Episodes of Gossip Girl: Scandals That Failed to Impress

Hey Upper East Siders, it’s time to dish on the worst episodes of Gossip Girl. As a self-proclaimed TV junkie, I’ve watched every episode of this iconic show, and let me tell you, there were some real clunkers in the mix. Whether it was cringe-worthy plotlines or downright terrible acting, these episodes are the ones that even die-hard fans skip over during a re-watch. But fear not, dear readers, as I’ve done the dirty work for you and compiled a list of the absolute worst episodes of Gossip Girl. So grab your headbands and get ready to relive some truly cringe-worthy moments. XOXO.
How to Succeed in Bassness

How to Succeed in Bassness

Season 3 – Episode 7

Air Date: 2009-10-26

In need of publicity for his new hotel, Chuck decides to move up his club’s opening and enlists Serena’s help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chuck’s approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivia’s infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.

The Return of the Ring

The Return of the Ring

Season 5 – Episode 24

Air Date: 2012-05-14

When Gossip Girl goes after Blair as she’s never done before, Serena admits she may have unintentionally played an important role in Blair’s latest nightmare. Meanwhile, Nate invites Lola to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode’s end, Blair will make a choice between the two men in her life…will it be Chuck or will it be Dan?

The Last Days of Disco Stick

The Last Days of Disco Stick

Season 3 – Episode 10

Air Date: 2009-11-16

Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien, the son of an ambassador who is staying at Chuck’s hotel, but the experience proves to be a lot more intriguing than she expected.

The Debarted

The Debarted

Season 3 – Episode 12

Air Date: 2009-12-07

On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma.

Rhodes To Perdition

Rhodes To Perdition

Season 5 – Episode 9

Air Date: 2011-11-28

Lily, Charlie and Serena eagerly anticipate the Studio 54 party being thrown in CeCe’s honor. Nate takes on a new role at the Spectator, but his first big story turns out to be about someone he knows all too well. Blair turns to an unlikely person for help.

Dirty Rotten Scandals

Dirty Rotten Scandals

Season 6 – Episode 3

Air Date: 2012-10-22

Feeling the pressure to make her first Waldorf Designs fashion show a success, Blair must rely on help from an unlikely source, but some unexpected scheming causes a scandal on the runway. Serena discovers that befriending Steven’s daughter Sage is trickier than she thought, especially when she is forced to put her issues with Blair aside to make Sage happy. Nate publishes Dan’s first serialized article causing a stir and producing a serious threat. Meanwhile, Chuck begins to look into the clue that Amira left behind, which may help uncover what Bart is hiding.

G.G.

G.G.

Season 5 – Episode 13

Air Date: 2012-01-30

The much-anticipated 100th episode will open with a musical dream sequence featuring Serena, Blair and all the men in their lives. Also, while Chuck wrestles with the reality that Blair is about to walk down the aisle with Prince Louis, the return of Georgina Sparks might make the royal affair a royal disaster.

Salon of the Dead

Salon of the Dead

Season 5 – Episode 20

Air Date: 2012-04-16

To celebrate their official coming out as a couple, Blair and Dan host a glamorous British-themed Salon, including guests Julian Tepper and Jenna Gribbon Lola lands the audition of a lifetime, but Gossip Girl may have other plans for the Upper East Side’s latest It Girl. Meanwhile, Lily and Rufus disagree over the best way to handle the Ivy situation, and Serena and Diana face-off over secrets they both would prefer remain secrets.

Despicable B

Despicable B

Season 5 – Episode 21

Air Date: 2012-04-23

Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that doesn’t happen. Meanwhile, Lily throws a family gathering – including William, Carol and Lola – in an attempt to prove the van der Woodsen family is as united as ever. Finally, Nate digs into Diana’s past and is surprised by what he discovers.

Raiders of the Lost Art

Raiders of the Lost Art

Season 5 – Episode 22

Air Date: 2012-04-30

Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.

The Fugitives

The Fugitives

Season 5 – Episode 23

Air Date: 2012-05-07

Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne.

Carrnal Knowledge

Carrnal Knowledge

Season 2 – Episode 17

Air Date: 2009-02-02

Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.

The Big Sleep No More

The Big Sleep No More

Season 5 – Episode 7

Air Date: 2011-11-14

Several of our favorite Upper East Siders attend a performance of Punchdrunk’s provocative theater experience, “Sleep No More,” which translates to masks, anonymity and some surprising romantic twists by the end of the evening. Meanwhile, Diana sets her sights on Serena in her quest to ruin Gossip Girl. Dan is out on his book tour, but things aren’t exactly as they appear to his friends and family.

All The Pretty Sources

All The Pretty Sources

Season 5 – Episode 8

Air Date: 2011-11-21

Serena is hard at work planning a dream bridal shower for Blair, but it should come as no surprise that Serena has to plant some false information about the shower in order to keep Blair from finding out all the details. Chuck and Dan decide to spend the day together to distract themselves from the fact that they didn’t make the invite list for Blair’s shower. Nate and Serena find a silver bullet in Diana’s war against Gossip Girl, but struggle about whether to use it or not.

Gone Maybe Gone

Gone Maybe Gone

Season 6 – Episode 1

Air Date: 2012-10-08

After a brief encounter abroad, Chuck and Blair make a promise to each other about their relationship, which leaves them once again apart. Dan, with some help from an unlikely ally, Georgina, is writing a scathing tell-all book that can only mean trouble. As the sole head of The Spectator, Nate is making his own decisions and is ready to go up against Gossip Girl. As word spreads that Serena is missing, the gang bands together to find her and are shocked by what they find.

High Infidelity

High Infidelity

Season 6 – Episode 2

Air Date: 2012-10-15

Trying to prove herself in adult society, Serena hosts the Central Park Conservancy’s big gala, of which she is now the newest Board Member, and she and Nate both learn something shocking about their significant others. Blair prepares to debut her new fashion line, but a rival from her past holds the key to her future. With the help of Georgina, Dan lands some meetings with publishers, but he must decide if he is willing to sacrifice his integrity in order to get his work published. Meanwhile, Chuck tries to persuade Amira to help him look into his father’s past, even if it means jeopardizing Lily and Bart’s relationship.

The Empire Strikes Jack

The Empire Strikes Jack

Season 3 – Episode 16

Air Date: 2010-03-29

Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.

Memoirs of an Invisible Dan

Memoirs of an Invisible Dan

Season 5 – Episode 4

Air Date: 2011-10-17

After much deliberation, Dan decides to gather Serena, Blair, Nate, Chuck, Rufus and Lily to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair and Louis hit a crises point after Louis reads Dan’s book. Diana learns incriminating information about one of Nate’s friends and uses it to her advantage.

The Princess Dowry

The Princess Dowry

Season 5 – Episode 17

Air Date: 2012-02-27

Blair thinks Cyrus may have found a potential loophole in her prenup. Chuck and Georgina partner up in a scheme, but it has an unpredictable outcome.. Meanwhile, a family crisis brings William van der Woodsen back to the Upper East Side.

Con-Heir

Con-Heir

Season 5 – Episode 18

Air Date: 2012-04-02

Chuck invites Jack to town to thank him for saving his life, but finds the trip doesn’t go exactly as planned. Blair and Dan attempt to consummate their new relationship — but unexpected roadblocks get in their way. Meanwhile, Ivy finds an unlikely ally in William in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper.