Exclusive Inside Scoop: Unveiling Blair & Jack's Scandalous New Year's Affair!

Summary

Blair and Jack Bass had a secret encounter on New Year's, but it was never explicitly revealed or explained on Gossip Girl.

Blair and Jack's secret may have been based on unverified information from Gossip Girl, hinted by a tip on the computer screen. Gossip Girl's revelations left numerous mysteries unanswered, such as why Chuck allowed his father to perish and why Chuck and Nate utilized public transport despite their wealth.

What really transpired between Blair (portrayed by Leighton Meester) and Jack Bass (played by Desmond Harrington) on New Year's Eve in the television series Gossip Girl? The CW drama delved into the lives of the New York elite, with an anonymous blogger known as Gossip Girl tantalizing fans with juicy details about the scandalous happenings on the Upper East Side. While the show featured various storylines, all eyes were always on Blair Waldorf and Serena van der Woodsen (portrayed by Blake Lively) — their actions, their fashion choices, and most importantly, their romantic relationships.

Serena's love life was tumultuous, as she dated multiple men, making it difficult for fans to predict her ultimate partner. Blair's romantic journey, on the other hand, followed a slightly different path — while she had her fair share of suitors, and even entered into a marriage with a prince, it was abundantly clear that her heart belonged to Chuck Bass (portrayed by Ed Westwick), Gossip Girl's Chuck Bass. Despite numerous breakups, they always found their way back to each other, ultimately ending up together. However, there was a period in Blair's life when she hadn't yet developed feelings for Chuck, which led to an unexpected encounter between Blair and Jack Bass, Chuck's uncle.

Who Was Jack Bass?

What Jack & Blair Did On New Year's

Introduced in season 2, episode 14 of Gossip Girl, titled "In the Realm of the Basses," Jack was the head of Bass Industries in Australia and resided there. He returned to New York after receiving news of his brother, Bart Bass' (played by Robert John Burke) death. As Chuck's sole surviving relative, he assumed the role of his legal guardian, bringing him back from an adventure in Asia following the passing of his father. However, tensions arise between the remaining Bass men when Jack discovers that Bart left the company to his son instead of him. This leads to a tense power struggle between the two. Adding to the complexity, Blair's secret relationship with Jack in Gossip Girl would have worsened matters even further. So, what exactly occurred on New Year's in Gossip Girl?

After successfully rescuing Chuck from the rooftop, Blair engages in a conversation with Jack Bass regarding the events of New Year's. She adamantly expresses her belief that Chuck should never uncover the truth about that particular night. Although the specific New Year's that Blair refers to remains unspecified, considering Jack's absence from New York until that juncture, it can be deduced that this incident occurred prior to the commencement of Gossip Girl.

In the series finale of Gossip Girl, titled "The Goodbye Gossip Girl," Jonathan Whitney reveals to Serena, Jenny Humphrey, and Eric van der Woodsen that he hacked into Gossip Girl's server and found all the tips he had been receiving. Among the files on the computer monitor, there is a tip from Joel Custer stating that Blair Waldorf hooked up with Jack Bass on New Year's Eve. Eric and Serena theorize that Gossip Girl may have held off on sending those emails because he couldn't prove their accuracy, suggesting that the information about Blair and Jack may have been unverified at that time. However, considering Blair's insistence that Chuck never finds out, it is likely that her secret involves her previous involvement with his uncle. Furthermore, now that it is revealed that Dan Humphrey was Gossip Girl, it is possible that he purposely withheld damaging information about those close to him.

Gossip Girl Left Other Questions Unanswered

What happened on New Year's between Blair and Jack Bass is only one of so many unanswered Gossip Girl questions. The unanswered questions range from the menial to huge series mysteries. At the beginning of the series, Chuck and Nate take a bus to school, and while that doesn't seem out of the ordinary, the two would never get public transportation given how filthy rich they are. There are other big-picture questions too, such as why Chuck let his dad die. Chuck refusing to save his father was one of the most macabre and extreme moments in Gossip Girl, and there was no clear reason what made Chuck stand back.