10 Worst Things Gossip Girl Did To Blair Waldorf


  • Blair faced constant hardships and betrayals from those closest to her, including her best friend sleeping with her boyfriend and leaving the city without warning.
  • Her family life was dysfunctional and complicated, with her father leaving her for a man and her mother prioritizing her fashion empire over their relationship.
  • Blair’s relationships with Chuck were filled with heartbreak, from him running away after she said “I love you” to him trading her for a hotel and sleeping with her arch-rival.



Although Gossip Girl‘s Blair Waldorf was the glamorous Queen Bee of the Upper East Side, she was no stranger to hardship and woes, with a number of terrible things being done to her over the course of the show. A complex and fascinating character, Blair quickly became one of the most intriguing parts of the show. Her relationships with her fellow characters, including Serena and Chuck, added to the nonstop drama of this scandalous show and made for a number of interesting storylines.

Despite her undeniable privilege and untouchable facade, Blair’s life was actually incredibly complicated. Her situation at home was far from ideal and her fierce loyalty often served as her downfall. Every season of Gossip Girlhas her facing some unbelievable hardship that would lead many of the other characters to crumble. Blair managed to handle it all in stride, though, and her ambition and determination allowed her to push forward and accomplish her lofty goals.

10 Blair’s Best Friend Slept With Her Boyfriend & Then Left The City

Season 1, Episode 1, “Pilot”

Blair and Serena sitting on the steps in Gossip Girl

Although best friends, Serena did a number of really terrible things to Blair. In the very first episode, it was revealed that Serena slept with Blair’s boyfriend, Nate. This is obviously an awful thing to do, but it managed to get even worse with the revelation that Blair had been in love with him since kindergarten. Then, Serena added to the betrayal even more by deciding to high-tail it out of New York City to a boarding school in Connecticut, without letting Blair know what happened. This meant that Blair was still with Nate, completely in oblivion about his indiscretions, and also lost her best friend with no warning.

Related: Gossip Girl Cast – Where Are They Now?

9 Blair’s Dad Left Her Family & Then Moved Away To Another Country

Season 1, Episode 1, “Pilot”

Blair's dad is giving her a hug in Gossip Girl.

In the pilot episode of Gossip Girl, Blair explains to Serena that her father left her mother for a man. He moved to Paris to be with his partner, which was very hard on Blair because she looked up to her dad and was very close to him. Blair was also navigating an eating disorder during the early seasons of the show, and her mother was emotionally unavailable. To leave Blair without any adults besides Dorota, invested in her well-being and being there for her day-to-day was awful and made her feel unloved at times.

8 Blair’s Mother Replaced Her With Her Best Friend For A Modeling Job

Season 1, Episode 4, “Bad News Blair”

Blair and Eleanor are eating in Gossip Girl.

Unfortunately, Blair and her mother, Eleanor, were never able to develop a strong mother-daughter relationship. Eleanor remained extremely focused on building and maintaining her fashion empire, which left little time to tend to her teenage daughter. This left Blair desperate for Eleanor’s attention and approval, which led her to participate in a photoshoot for her mother’s new line. At the last minute, Eleanor made the decision to replace Blair with Serena in the shoot. This came as a huge betrayal to Blair, who was excited about doing something with her mom, and it was made worse by the fact that Serena became her replacement, who she already compared herself to.

7 Blair Said “I Love You” To Chuck, Only For Him To Run Away

Season 2, Episode 13, “O Brother, Where Bart Thou?”

Blair and Chuck in white in the season 2 premiere of Gossip Girl

Given how complicated Blair and Chuck’s relationship was, it doesn’t come as a surprise that the two turned saying “I love you” into a twisted game. When Chuck’s father died, Blair decided to swallow her pride and “lose” by being the first to say those three important words. Chuck doesn’t say them back and, instead, leaves the scene entirely, leaving Blair crushed and humiliated.

Seeing Blair feel so strongly for Chuck and wanting to help him through his dad’s death, only to be shut down made for one of the most heartbreaking moments of the show. She manages to get herself to say it to him again, later on in the show, only for him to turn away from her for a second time. Blair was known for being closed off and mean at times, so it was unfortunate that Gossip Girl made one of her most vulnerable moments go so terribly.

6 Blair’s Boyfriend Traded Her For A Hotel

Season 3, Episode 17, “Inglorious Bassterds”

Blair and Chuck meet on a bridge in Gossip Girl

One of the most shocking and memorable parts of Gossip Girl is when Chuck decides to trade Blair to his uncle for his hotel. The fact that he was able to go through with this twisted plan and use Blair in such an awful way was horrific. It made Blair question their entire relationship and come to the conclusion that the two of them were no good together. Given how emotionally invested Blair was in Chuck, this was a devastating thing to have happened to her. It was made worse by the fact that Chuck took advantage of Blair’s love and her commitment to stand by him no matter what.

5 The Love Of Blair’s Life Slept With Her Arch Rival

Season 3, Episode 22, “Last Tango, Then Paris”

Chuck and Blair are talking while Blair holds flowers in Gossip Girl

Blair and Jenny had a deep-seated rivalry, so it came as the ultimate betrayal when Chuck slept with Jenny after Blair didn’t show up at the Empire State Building. The truth came out right as Chuck got down on one knee, ready to propose to Blair, which made things even worse. This was a moment Blair had dreamed about, and it was so terribly marred by this news. Given how deeply in love Blair was with Chuck and how she was willing to move past the horrible hotel situation he put her through, it was devastating that he hurt her once again.

4 Blair Got In A Car Crash & Lost Her Baby

Season 5, Episode 10, “Riding In Town Cars With Boys

The car accident was horrible for Blair for multiple reasons. She lost her baby as a result of it, which was very damaging for her. On top of that, she did not know if Chuck was going to survive. In a moment of desperation, she promised God that she wouldn’t be with him and would, instead, follow through on her promise to marry Louis if Chuck survived. When he did survive, Blair was forced to keep herself from being with him, despite so badly wanting to. Before the accident, Blair was prepared to marry Chuck and raise her baby together, so this terrible car accident completely derailed her future plans.

3 Blair’s Husband Only Married Her To Keep Up Appearances

Season 5, Episode 13, “Father And The Bride”

Blair decided to go through with her wedding, despite her undying love for Chuck, because of a promise she made to God. She couldn’t help but share with Chuck, one more time, that she loved him on the day of her wedding. She was unknowingly being recorded, and Louis ended up seeing the video. It would have made perfect sense for Louis to have felt extremely hurt by this and call off the wedding but instead, he pretended to forgive her and the day carried on. After they were officially married, he revealed that they would only be married in name only and that she was dead to him.

Louis’ hurt was completely justified, but this was an awful situation for Blair to be put in. She was forced to scramble to figure out a plan to get a divorce and, ultimately, had to continue on with the marriage to save her family from financial ruin. Given that she had pure intentions of saving Chuck by getting married, it was unfair that an entire year of her life was derailed by this.

2 Blair Watched Her Boyfriend Kill His Dad

Season 6, Episode 9, “The Revengers”

Blair and Chuck in formal attire in Gossip Girl

Although Blair was well aware of Bart’s villain-like behavior in Gossip Girl, it was still scary for her to watch Chuck push him off the side of a building to his death. Blair was then put in a position of having to help Chuck cover up the murder and went on the run with him. While it leads to her getting what she had always wanted, marrying Chuck, it was still traumatic to have to watch this unfold and have to figure out how to save the love of her life from getting in serious trouble.

1 Blair Had Her Entire Life Under A Microscope Thanks To Gossip Girl

Season 1-Season 6

One of the worst things Gossip Girl did to Blair Waldorf was having her entire life dissected by the masses thanks to the online gossip site. So many horrible things happened to her as a result of this, like being terrified about going back to school after Gossip Girl outed her worries about being pregnant or her whereabouts being revealed when she was running away from Louis. Even the pages of her diary were leaked to the site, causing her personal relationships to become strained. Given that Gossip Girl ended up being Dan, someone she dated at one point, it was even more cruel that all of this went down.

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