Top 10 Saddest Gossip Girl Moments

Chuck and Blair notoriously love playing games with each other. But when it comes down to it, they share a genuine connection. At least that’s what Blair thought at the end of season 2. After spending time in an on again off again relationship, both parties end up betraying the other by sleeping with someone else. But Blair thought all would be forgiven if she finally told Chase those 3 little words. Unfortunately, he was not so quick to forgive. Thankfully, this break was only temporary and the couple would eventually endure. But the scene was absolutely devastating at the time.

Jenny and Eric fit so perfectly in the sibling relationship that they never asked to be put into. They definitely fight and bicker like family. But when Jenny is really in need of support, Eric is often there for her. Initially their friendship started out to fight the power-hungry Queen that was Blair Waldorf. But after Blair leaves Constance, Jenny gets the crown and slowly turns into a vindictive mean girl. Her new mean streak drives a wedge between her and her stepbrother. After messing with Serena’s relationship and sleeping with Chuck, J is at her lowest point. At least Eric is there for her for this dark moment.

Through an elaborate plan of schemes and faking identities, Georgina Sparks exposed some of Serena’s darkest secrets to her boyfriend Dan. Although this plot broke them up, their fiery chemistry brought them back together at the start of the next season. Unfortunately, they never worked out the problems that split them up in the first place. The couple gets locked in an elevator going to a party and are forced to face their crumbling relationship. Serena and Dan brought out the best in each other. This is why many fans were gutted to see them fall apart during this episode.

Rufus has always made sure to try to keep a tight knit relationship with his kids. When Jenny started to turn rotten, he still fought to keep her on the right path. Even when she ruined the charity event that Lily hosted, he stood by her. But Jenny takes it a step too far when she tries to mess with both his relationship as well as Dan and Serena’s. After Rufus finally sees her behavior as destructive to those around her, he and little J’s mom Alison make a decision. Jenny has to move in with her mom. Despite everything J has done, her goodbye to her family is nothing but heartfelt.

Chuck puts on this facade that makes him seem like a heartless, uncaring person. But his father broke that facade. C had a tumultuous relationship with his father Bart. And when you found out how awful his dad was, it’s hard to blame him. But the young Bass took it very hard when Bart “died” in season 2. At the funeral Chuck is not even recognizable as the man who was all about girls, business, and always being best dressed. While in mourning, he decides to throw a party at the club he bought. But in his sorrow, he ends up on the roof of the building dangerously close to the edge. Watching Blair talk him down was almost too much to handle.

Chuck and Blair. Blair and Chuck.Their names even sound like they are meant for each other. The “it” boy and the mean girl indulged in games with each other for years, even when they were broken up. But as they grew into adults, the stakes in the game grew also. A serious rift eventually formed between the two. And just when it seemed like B was getting her fairytale ending on her own, C came back. And so did all of their passionate feelings for one another. He showed up on her wedding day to tell her not to marry a literal prince...and she turns him down. We still get chills watching this extremely emotional scene.

As an audience, it can sometimes be agonizing to watch Chuck and Blair pretend like they are not absolutely perfect for each other. C had a really rough year throughout the second season of the show. And B stood by him, for the good and especially for the bad. But when Nate wants Blair she has to give Chuck an ultimatum. And he turns her down this time around. It’s hard to watch Blair’s heart shatter. To make matters more emotional, we learn that Chuck didn’t even mean his cruel words in the very next scene. He just loved her so much that he wanted her to have someone better than himself.

After much suspicion we finally learn that Blair really is pregnant. In the wake of her and Louis revealing they are expecting, a ton of drama unfolds. At the same time, she comes to terms about how she feels about Chuck. But everything takes a dark turn when the two get in a car crash. While Chuck is severely wounded, Blair loses her baby. This tragedy encourages B to keep her distance from him in order to keep them both safe. Watching Blair lose the most important things in her life is absolutely soul crushing.

Before there was Chuck and Blair, there was Blair and Serena. Their lifelong friendship was also full of ups and downs. But one of the lowest points came when Serena left Manhattan. When she returns, she sees Blair trying to tear her friend down. Eventually, B decides it's time for the truth and reads S the letter she wrote for her but never sent. It makes for a raw and emotional experience. We finally get to see what is behind B’s mean girl armor. Seeing how sad Blair is and how rough her family and friendships have been definitely made us feel bad for her.

Before we unveil our top pick, here are a few honorable mentions.

Eric Sets Blair Straight
Blair Accuses Serena of Being in Rehab, but Eric Tells Her He Was the Patient

Serena Stands up for Herself
Dan Tries to Fight for Serena, but She Tells Him She Doesn’t Belong There

Serena Opens up About Her Father
He Left for a Business Trip & Never Came Back

Nate Has His Dad Arrested
His Father Truly Crossed A Line

Serena Tells off Her Dad
Her Dad Wants to Know His Other Daughter & She Tells Him How She Feels About It

Chuck was willing to have Blair be with Jack for a hotel. That definitely bears repeating. Chuck would’ve let Blair, someone who truly loved him, sleep with another man for a hotel. This horrendous moment of lapsed judgement was made worse by the fact that Chuck orchestrated it. Although he tries to defend himself, Blair lets her emotions out. Chuck has done a lot of horrible things to Blair in the name of their game. But he truly outdid himself with this betrayal. In the end, he does grow from the mistake and redeem himself with his one true love. But this depressing scene still sticks with us.