10 Unanswered 'Gossip Girl' Questions The Reboot Def Needs To Explain

Despite being in love with Serena for pretty much the entire series — as well as falling for Blair, Vanessa, Juliet Sharp, and even one of Serena's short-term boyfriend's daughter, Sage — Nate ended up alone at the end of the series. While his job at The Spectator seemed to be going well (at least, judging by the private jet he stepped out of) and he hinted he'd be running for mayor, he attend Serena and Dan's wedding sans date.

Maybe his character evolved, but for someone so cute with such a desire to find ~the one~, it's strange he was the only main character without a special someone.

From the very first episode, it was clear the Upper East Side teens partied. But instead of just stealing booze from their parents' well-stocked liquor cabinets, they were running around the city buying bubbly and, in Chuck's case, an entire bar. Just because they're well-known socialites, that doesn't mean every establishment would be down to risk their liquor licenses to serve some spoiled minors, right? So, how did they manage to always get drinks, and will the new generation be just as stealthy?

Vanessa was a crucial part of the show (much to Blair's dismay), but after making up and breaking up with Dan a few times — both platonically and romantically — she eventually peaced out and left the city for good. Even though she got a good opportunity in Spain, it seemed like a pretty extreme departure, since she and Dan were lifelong friends.

What's more, she still cared enough to be getting Gossip Girl/Spectator blasts from across the pond, which means she probably wasn't as over the Upper East Side as she made it seem. Considering everyone forgave Dan for, well, everything, it's kinda sh*tty V was still left out in the cold.

During Season 2 and 3, Scott Rosson, who turned out to be Rufus and Lily's love child, was introduced. After bonding with the Humphreys and van der Woodsens, and even standing by their side as his parents said "I do," it seemed like there was going to be another main character on the show. In fact, he even said Lily invited him to come back anytime (and that he planned to take her up on the offer), but oddly he was never seen again.

Even though everyone acted like Scott was ~family~, he literally just disappeared, which is pretty strange since Rufus loved to play the "best dad ever" card. Ultimately, it doesn't even make sense why Scott was introduced, other than to make Dan and Serena's (bad) relationship a little bit more taboo.

The story of Chuck's mom is so fuzzy and complicated, it seems like the writers just wanted to make viewers as pissed about her identity as Chuck was. In the pilot episode, Chuck referred to his mother in the present tense (saying he should have swiped some of her antidepressants) and gave no hint that she's dead. But then the fact that he thought she died during childbirth and had lots of guilt surrounding it was a major plot point in the first few seasons.

This is confusing on its own, but then add in the whole "wait his mom might actually be alive" storyline and things got really wild. First, it seemed like Elizabeth Fisher (aka Evelyn Bass) was Chuck's mom. But then she said she was actually lying just to get his hotel for his uncle Jack. And then Diana Payne said she was his mom, but it seemed like that was just a front to hide the fact that Chuck's dad, Bart, was still alive. Ultimately, it looks like Elizabeth Fisher/Evelyn Bass actually is his mom, but the inconsistencies are enough to stress out even the chillest fan.

If there's one episode you should skip during a rewatch, it's probably the "Valley Girls" episode (Season 2, Episode 24). While the episode was originally supposed to serve as a backdoor pilot for a spinoff, the new show never got picked up, which made for a lot of open storylines. Throughout the episode, after having Serena thrown in jail, Lily had flashbacks to getting arrested when she was younger. The episode showed a young Lily (Brittany Snow) running away to live with her sister, Carol (Krysten Ritter), in Los Angeles. It's there that Lily met a few people who seemed like they'll matter in the series, only for them to be completely forgotten about.

First, there's Owen, the cute guy who worked with Carol. Young Lily was seen flirting and dancing with him throughout the episode, and it was pretty clear there were some major sparks and relationship potential there. Except Owen was never mentioned again in Lily's backstory, and neither was Keith van der Woodsen, who young Lily also met in Los Angeles. While Keith is probably related to Lily's future (ex) husband, William, none of it was ever explained.

Few characters in the history of television have as much turmoil as Jenny and Blair, which is why the final episode is so confusing. After literally banishing Jenny from the city, Blair made it clear she absolutely despises the youngest Humphrey, especially after it was leaked that Chuck slept with Little J. So, Jenny went away to live with her mom in Hudson and Blair happily went on to torments others.

When Jenny was seen carrying a "J by Waldorf" bag in the final episode, however, it's clear she has a line through Waldorf Designs. Granted, she worked for the company on and off and she definitely had drive and talent, but B and J could barely co-exist in the same city together. How could they possibly have a respectful and functioning working relationship?

After a stressful Season 1, in which Jenny and Dan's mom (who had moved out of the family's Brooklyn loft "to think") came back to the city and got back together with Rufus, she then decided things just weren't going to work out. And just like that, Alison Humphrey all but vanished.

While her name was brought up on occasion (like when Jenny got written out of the show and her character went to "live with Alison" in Hudson), by the end of the series, it was like she never existed. You'd think she'd at least make an appearance at Dan's wedding, but the mother of the groom was no where to be seen.

When Lily's sister, Carol, hired Ivy Dickens to pretend to be her daughter in order to get access to her trust fund, it all mades sense in an Upper East Side kind of way. The problem, however, was the fact that when Ivy (pretending to be cousin Charlie) bumped into Serena for the first time, they reminisced about being on a yacht when they were 12. When the real Charlie (who goes by Lola) came into the picture and confronted her mom, she mentioned being hidden away and never knowing that part of the family existed. So was Lola being dramatic (she was an actor, after all), or did Carol just hire fake Charlies for Lola's whole life?

I'm not the first — and I definitely won't be the last — fan to be perplexed by Gossip Girl's true identity. Even though the reasoning behind the decision makes sense (Dan wrote himself into that elite world! Genius!), the fact that there were so many times Dan himself was shocked by a Gossip Girl blast took away from the big reveal. Why would he have to act like a surprised reader when he was, say, alone in his loft?

Regardless, the series will forever be a classic, even if some of the finer print doesn't exactly add up. Manicured fingers crossed the reboot is just as iconic, with a few fewer plot holes.

The original Gossip Girl is streaming now on HBO Max and the reboot is set to premiere on the streamer sometime in 2021.