Summary
- Blair and Jack Bass had a secret encounter on New Year's, but it was never explicitly revealed or explained on Gossip Girl.
- The secret between Blair and Jack may have been unsubstantiated information held by Gossip Girl, as hinted by a tip on the computer monitor.
- Gossip Girl left many unanswered questions, including why Chuck let his dad die and why Chuck and Nate would take public transportation despite their wealth.
What really happened between Blair (Leighton Meester) and Jack Bass (Desmond Harrington) on New Year's in Gossip Girl? The CW drama revolved around the high society lives of the New York elite, with anonymous blogger Gossip Girl feeding his fans with the most salacious information in the Upper East Side. While the show tackled a string of narratives, the focus was always on either Blair Waldorf and Serena van der Woodsen (Blake Lively) — what they did, who they wore, and most importantly, who they were dating.
Serena's love life was a roller coaster; she dated various men making it difficult for fans to gauge who she'd end up with. Things were a little different for Queen B — while she went out with a string of guys, and even got married to a prince, it was always clear that her endgame was Gossip Girl's Chuck Bass (Ed Westwick). No matter how many times they broke up, they kept on coming back to each other, ultimately ending up together. However, there was a point in Blair's life when she wasn't yet hung up on the youngest Bass, leading to an encounter between Blair and Jack Bass, Chuck's uncle.
Who Was Jack Bass?
Introduced in Gossip Girl season 2, episode 14, "In the Realm of the Basses," Jack ran Bass Industries in Australia and was based there; he only returned to New York following news of his brother, Bart Bass' (Robert John Burke) death. As his only surviving relative, he became Chuck's legal guardian, bringing him home from an Asian escapade following the demise of his father. However, things go awry between the remaining Bass men when Jack finds out that Bart left the company to his son instead of him. What follows is a tense tug-of-war between the two, and if that's not complicated enough, Blair's secret with Jack in Gossip Girl would've made things a lot worse — but what happened on New Year's in Gossip Girl?
What Jack & Blair Did On New Year's
At the end of the same episode, after Blair successfully brought Chuck down from the rooftop, Blair and Jack Bass have a discussion about what happened on New Year's. Blair tells Jack that his nephew should never find out about that night. There's no indication what New Year's she's actually talking about here, but since Jack didn't return to New York until that point, it's safe to say that this happened before Gossip Girl began.
Gossip Girl never explicitly provided an answer about this topic even though Jack appeared in the series a handful more times, but later in the season 2 finale, entitled "The Goodbye Gossip Girl," Jonathan Whitney (Matt Doyle) revealed to Serena, Jenny Humphrey (Taylor Momsen), and Eric van der Woodsen (Connor Paolo) that he hacked into Gossip Girl's server and discovered all the tips he's been getting. Zooming in on the files on the computer monitor, there's a tip from Joel Custer that "Blair Waldorf hooked up with Jack Bass on New Year's Eve!"
As Eric and Serena said, their theory was that Gossip Girl held off from sending those emails because he wasn't able to prove them yet, meaning that the information about Blair and Jack Bass might have been unsubstantiated at that time. That being said, there are very few choices as to what their secret is and why Blair was insistent that Chuck never finds out about it — having previously hooked up with his uncle is one of them. In addition to that, since Dan Humphrey (Penn Badgley) was the Gossip Girl all along, it's also possible that he intentionally withheld tips that could seriously harm those close to him.
What happened on New Year's between Blair and Jack Bass is only one of so