Gossip Girl is known for its fair share of high drama, and while characters like Blair Waldorf and Serena van der Woodsen often took center stage in the world of elite scandals, Vanessa Abrams—although a bit of an outsider—also had her moments of epic embarrassment.

Whether she was trying to fit in with the Upper East Side’s elite or navigating her relationships with the main characters, Vanessa often found herself in awkward, cringe-worthy situations. Here are 10 times Vanessa embarrassed herself on Gossip Girl:

1. When She Tried to Fit In With the Upper East Side Crowd

• From the start, Vanessa was the outsider trying to break into the world of wealth and privilege that Blair, Serena, and Chuck navigated effortlessly. Vanessa’s attempt to fit in was often painfully awkward, and no one could miss her efforts to “class up” her look and behavior to match the elite standards. Whether it was attending high society events or trying to align with Blair and Serena, Vanessa’s discomfort and need to belong often came off as desperate and forced, embarrassing her in front of those she wanted to impress.

2. The Nate Kiss That Was Awkwardly Public

• One of Vanessa’s most awkward moments occurred when she kissed Nate Archibald, despite knowing that he was still emotionally involved with Serena. In the world of Gossip Girl, kissing another character in front of your ex is a fast track to embarrassment—and that’s exactly what happened when Vanessa couldn’t hold back her feelings for Nate. The public kiss stirred up tension with Serena, Nate’s feelings remained unclear, and Vanessa was left feeling exposed and caught in a very messy love triangle.

3. When She Called Out Blair at the Party

• Vanessa and Blair were never the best of friends, and their rivalry came to a head during an intense moment when Vanessa tried to publicly call out Blair at a party. Her attempt to take down Blair backfired spectacularly as she was quickly shut down by the queen bee herself, leaving Vanessa humiliated in front of their high-society peers. The scene highlighted just how out of place Vanessa was trying to challenge Blair, who had long been the reigning queen of the Upper East Side.

4. Her Failed Attempt to Be Gossip Girl

• In one of her more cringey moments, Vanessa tried to use Gossip Girl’s platform to take down the elite world of Manhattan that had always made her feel like an outsider. By attempting to expose secrets and take control of the Gossip Girl empire, Vanessa found herself being humiliated as it became clear she was out of her depth. Her plan didn’t work, and she ended up looking foolish in her effort to manipulate the scandalous world that had so often ridiculed her.

5. When She Exposed Her Relationship with Dan

• While Vanessa’s relationship with Dan Humphrey was not exactly embarrassing in itself, the way she chose to reveal it definitely was. She announced it publicly, in a very clumsy way, making sure that the entire social scene knew about their relationship. The timing couldn’t have been worse—Dan was already entangled with Serena at the time. Vanessa didn’t exactly win any social points by making such a dramatic reveal, leaving her looking like the other woman and making everyone around her uncomfortable.

6. Her Drama with Jenny at the Fashion Show

• The showdown between Vanessa and Jenny Humphrey at the fashion show is one of the most awkward moments of Vanessa’s Gossip Girl run. Vanessa was completely out of her element, trying to get involved in the fashion world while still maintaining her outsider status. When Jenny shut her down at the show, Vanessa was left embarrassed, looking like she didn’t belong in the high-fashion environment that was so natural to Jenny. The public confrontation did not help Vanessa’s social standing one bit.

7. When She Was Caught Lying About Being Friends With Blair

• Vanessa often tried to pretend she was closer to the Upper East Side clique than she actually was, and one of her most embarrassing moments came when she was caught lying about being friends with Blair. When Vanessa falsely claimed she was tight with Blair to gain favor or make herself more important, it backfired. Blair quickly called her out, and Vanessa was exposed for her attempt at social climbing, leaving her looking more foolish than ever.

8. Her Desperate Attempt to Break Up Dan and Serena

• Vanessa’s jealousy and bitterness toward Serena often led her to make questionable decisions, including trying to break up Dan and Serena in several embarrassing ways. At one point, Vanessa tried to sabotage their relationship by involving herself in their personal drama and creating conflicts where none existed. She ended up looking petty and vindictive, only alienating her friends and confirming that she was more of a troublemaker than a trustworthy confidante.

9. When She Stole the Spotlight at Rufus and Lily’s Wedding

• Vanessa’s ill-timed drama at Rufus and Lily’s wedding made for one of the more cringeworthy moments in her storyline. At a time when everyone was supposed to be celebrating, Vanessa tried to stir up problems with Dan and Serena’s relationship and drew unwanted attention to herself. Her behavior, while dramatic, was completely out of place and made her the center of attention for all the wrong reasons, embarrassing herself and ruining the mood at the celebration.

10. Her Relationship With Dan After She Told Him She Was in Love with Him

• Vanessa’s confession of love for Dan was one of her most cringe-worthy moments, as it was clear he didn’t feel the same way. When she opened up about her feelings for him, Dan didn’t reciprocate, leaving her feeling exposed and awkward. This not only strained her relationship with Dan but also made her appear vulnerable in a way that she hadn’t anticipated. Her emotional honesty in that moment was not met with the return of affection, which only amplified the awkwardness of the entire situation.

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While Vanessa Abrams might not have had the level of drama that some of the other Gossip Girl characters experienced, her moments of embarrassment were both frequent and unforgettable. Whether she was trying too hard to fit in, causing unnecessary drama, or simply misreading the social dynamics of the Upper East Side, Vanessa managed to give fans a fair share of cringey moments. Despite her awkwardness and misguided decisions, Vanessa’s character left a lasting impact on the show, proving that even the most “out-of-place” characters can find themselves at the center of high drama.