The television show Gossip Girl made a big splash in the media when it came out. It aired on September 19, 2007 on The CW, and there was almost nothing like it. It had all the drama of a soap opera, but had all the ritz and success of a higher-brow show. Plus, it was aimed at a teen audience. The teens seemed to be worldlier than the teens of shows like The O.C. or One Tree Hill. At one point, New York magazine even called it the “Greatest Teen Drama of All Time.”
The show is narrated by the omniscient blogger known as Gossip Girl, who is voiced by actress Kristen Bell. Throughout the entire series, viewers are left to wonder who Gossip Girl is. The show follows upper class “it” girl Serena van der Woodsen –played by Blake Lively—through her life and experiences with her friends (and frenemies) as she takes over Manhattan’s Upper East Side. The plot also follows Penn Badgley’s character Dan Humphrey, who—because of his socio-economic status—is an outsider looking in at the glamorous lives of his Upper East Side counterparts.
If you already knew all that stuff, and consider yourself a big fan, be aware that this quiz has a lot of spoilers. It is only for real fans who know all the ins and out to the lives of S, the Queen Bee and Lonely Boy.
1Where was Serena when she left the city for a year?
The first character viewers meet in the pilot is Serena van der Woodsen. She is gorgeous, blonde and has legs for days. She is the daughter of William and Lily van der Woodsen. She has been away, but is now back in New York City. She comes to realize that a lot has changed in her world while she was away. A lot of her friends are not pleased that she is back, especially her best friend Blair Waldorf. She was away from the city for a year. Where was she?
2Where do Nate, Chuck, and Dan go to high school?
Nate Archibald is considered the “golden boy of the Upper East Side.” He starts the show dating Blair, but then things get hairy. Chuck Bass is Nate’s best friend and is the TV show’s bad boy that viewers love to hate. He is probably the character who viewers see grow the most. Dan, like mentioned earlier, is an outsider looking in who manages to get a scholarship to the same school where Nate and Chuck also attend. Where do Nate, Chuck, and Dan go to high school?
3Which character was played by a different actor or actress in the pilot?
The gorgeous Serena van der Woodsen is played by Blake Lively, who originally turned down the role because of plans to go to college. Blair Waldorf is played by Leighton Meester, who dyed her hair brown for the audition. Chuck Bass is played by the British actor Ed Westwick, who originally tried out for the part of Nate, but casting directors said he looked too much like a serial killer. Which character was played by a different actor or actress in the pilot?
4Which of Blair’s parties does Jenny make invitations for to gain a spot on the guest list?
Much like her brother Dan, Jenny Humphrey is an outsider looking in. But unlike Dan, Jenny longs more than anything to be part of the Upper East Siders’ inner circle. She is a social climber who will bend over backwards to please Blair, and Blair knows it. Blair often uses Jenny for her own benefit. Interestingly enough, Jenny does not realize that she doesn’t need Blair or any of the Upper East Siders. Which of Blair’s parties does Jenny make invitations for to gain a spot on the guest list?
5What kind of luxury vehicle are Blair and Chuck in when they get together for the first time?
Throughout the entire series, Blair and Chuck have a very on again-off again relationship. Though in the first season of the show she starts off dating Nate, she eventually seduces Chuck with a burlesque dance at his club because she found out that Nate still loves Serena. She loses her virginity to Chuck, and Chuck develops feelings for her, but she immediately regrets it. What kind of luxury vehicle are Blair and Chuck in when they get together for the first time?
6Nate’s family on the show claims to be descendants of which real-life famous family?
Nate Archibald was born to Howard “The Captain” Archibald and Anne Archibald. He is best friends with Chuck Bass. He hopes to be a politician one day. In the series finale, he announces that he intends to run for office as the mayor of New York City. Nate is easily the most pitiable character because he has a lot of family problems, a drug habit and is the only character at the end of the show who remains single. Nate’s family on the show claims to be descendants of which real-life famous family?
7What is Rufus’s favorite breakfast food to serve to his kids?
Rufus Humphrey is the father of Dan and Jenny. He is played by the actor Matthew Settle. After he graduated high school, he opted out of college to pursue a music career instead. Back in the day, he used to date Lily van der Woodsen, and is reunited with her when she comes to tell Rufus that their kids are going on a date together. Rufus is pretty close with his kids. What is Rufus’s favorite breakfast food to serve to them?
8What is the name of the doorman at the Palace?
When the show begins, Serena and her family live at The New York Palace Hotel – also called the Palace – which is owned by Chuck’s dad, Burt Bass. It is a grand luxury four-and-a-half-star landmark hotel along Madison Avenue in Midtown. At one point, the Van der Woodsens and the Bass family move in together when Lily and Bart get together. Chuck ends up getting kicked out of the family penthouse, but still has a space in his Palace suite. What is the name of the doorman at the Palace?
9Blair and Serena love to eat lunch at one of the real sites in New York City. Where is it?
Many of the locations referenced in Gossip Girl are real locations in New York City. For instance, in the pilot episode of the show, Serena is spotted getting off a train in Grand Central Station. Central Park is shown hundreds of times in the show, including as the site for Blair and Chuck’s wedding. The New York Palace Hotel that is owned by the Bass family in the show is a real hotel in Midtown. Blair and Serena love to eat lunch at one of the real sites in New York City. Where is it?
10Which one of these is not a real name of a Gossip Girl episode?
The titles of each episode in the Gossip Girl series are very clever. Each episode’s title is based off the name of a film, movie or book. For example, the episode “Seventeen Candles” was based off the ’80s masterpiece, Sixteen Candles. “The Serena Also Rise” is from the Hemingway novel titled The Sun Also Rises. Of course, “The Blair B*tch Project” is The Blair Witch Project. Which one of these is not a real name of a Gossip Girl episode?
11Where is Dan from?
Dan Humphrey does not fit in with the Upper East Siders at all. Right from the start, he has a hard time adapting to St. Jude’s School for Boys because he is on scholarship there. Like everyone else, he eventually gets caught up in the whirlwind that is Serena van der Woodsen. They have an on again-off again relationship throughout the show, mostly because they are from totally different worlds. She is from the Upper East Side, but where is Dan from?
12Who's the first person Serena dates when she returns to New York City from boarding school?
In the first episode, Serena returns from Cornwall, Connecticut where she went to The Knightley School, a boarding school. Before she left for school, viewers find out that she had a fling with Blair’s boyfriend Nate and that he is still in love with her. This makes Blair furious, but what makes her even more mad is that both Nate and Chuck pursue Serena upon her return to the city. Who's the first person Serena dates when she returns to New York City from boarding school?
13Serena’s mother, Lily, has an ex-boyfriend and an ex-husband with almost identical names. What were their names?
Lily van der Woodsen is an admirable character throughout the whole show. She is played by actress Kelly Rutherford. She grew up in California on a ranch and had a very different life before attending Brown and marrying William van der Woodsen. She even dated Rufus Humphrey before she was married. She is married a total of six times throughout the show, some we see, some are merely mentioned. Serena’s mother, Lily, has an ex-boyfriend and an ex-husband with almost identical names. What were their names?
14Which Disney actress guest-starred as Olivia Burke?
Olivia Burke is a character who shows up in Season 3 of the hit show. She is a famous actress, but introduces herself as Kate when she meets Dan—even though he has no idea who she is. Dan eventually pieces together who Kate is, but the two of them end up dating anyway. Vanessa Abrams, Olivia’s roommate and Dan’s childhood best friend, is jealous of Olivia and tries to sabotage Dan’s relationship with Olivia. Which Disney actress guest-starred as Olivia Burke?
15The show is based on books written by who?
Gossip Girl is not only a TV series, it is a book series. In fact, the show was based off the book series. There are 13 books in the series, written by an author as well as a ghostwriter. Many of the characters are very similar to the characters in the show, but the producers of the show took many liberties with the characters. A lot of the big plotlines are the same, but many of the smaller plot points differ. The show is based on books written by who?
16What was the name of Lily and Rufus’s secret son?
Before Lily married William van der Woodsen, she dated Rufus Humphrey. The pair had a love child that Lily did not tell Rufus about and whom she gave up for adoption. Their son shows up at the end of Season 2, unbeknownst to his biological parents. He befriends Vanessa and Dan. He even starts to take guitar lessons from Rufus. By season 3, Rufus and Lily find out who he is and have a wonderful reunion. What was the name of Lily and Rufus’s secret son?
17What is Serena’s dream college?
Though the characters’ lives are filled with drama, somehow each of the teens do well enough in school to go to top tier colleges. Dan pursues writing at NYU. Vanessa also attends NYU. Blair goes to both NYU and Columbia at different points in the show. Nate goes to Columbia though his family wanted him to go elsewhere. Chuck does not end up attending college and neither do Jenny or Georgina as they all have other pursuits. What is Serena’s dream college?
18By the end of the series, Georgina appears to be divorced and with Jack Bass at Dan and Serena’s wedding. Dan thought Milo was his what?
At the end of the season three finale, a very pregnant Georgina shows up. After she has Milo, she conveniently disappears because she needs a spa trip. When she returns from her trip, she explains the whole story. By the end of season four, Georgina and Milo live with Philip Becker, Georgina’s new husband. By the end of the series, Georgina appears to be divorced and with Jack Bass at Dan and Serena’s wedding. Dan thought Milo was his what?
19What test was Vanessa studying for when she met Nate?
Season one of Gossip Girl is all sorts of crazy for Nate Archibald. His dad is on drugs and he is very confused by his on again-off again feelings for Blair. He begins the show thinking that he is in love with Serena, but is still dating Blair. Eventually, they break it off and he regrets it. They get back together, but Blair had a fling with Chuck, Nate’s best friend, and he stops talking to both Chuck and Blair. In the midst of all the drama, he meets Vanessa. What test was Vanessa studying for when she met Nate?
20Where did Georgina go when she left New York City?
Georgina Sparks grew up with the Upper East Siders. She briefly attended high school with Serena and Blair, but left to tour the equestrian circuit. Unfortunately, she sold her pony for cocaine and was sent to boarding school. However, she shows up in season one and starts making a mess of things for Serena and eventually everyone else. Dan ends up working with Blair to take Georgina down. They summon Georgina’s parents back to town, and her parents send Georgina away. Where did Georgina go when she left New York City?
21How many seasons of Gossip Girl were there?
Gossip Girl began in 2007. In its heyday, the show succeeded greatly. Based on The New York Times bestselling novel series, the pilot received many positive reviews. Though it deviated from the novels greatly, people still ate it up as a guilty pleasure. Its final season had a very abrupt ending with only 13 episodes. In the final episode, Gossip Girl’s identity was revealed—and it led to a lot of controversy. How many seasons of Gossip Girl were there anyway?
22Which guy is Serena never related to at any point in the series, by blood or marriage?
There are many twists and turns throughout the show and many secrets are revealed. Who is related to who is constantly changing. Blair, for instance, ends up related to Chuck. She also is related to Lily van der Woodsen at one point. She even becomes Princess of Monaco when she becomes related to Louis Grimaldi. Serena becomes even more intertwined with all of the characters. Which guy is Serena never related to at any point in the series, by blood or marriage?
23Over the course of the series, which love interest did NOT consider proposing to Blair?
Blair is a total serial dater. She dated Lord Marcus Beaton briefly during season two of the show. She had a one night stand with Jack Bass, Bart Bass’s slimier younger brother. She even had a hot fling with Carter Baizen, who appears on and off throughout the whole show. She manages to date just about everyone, including Chuck, Nate, Dan and Prince Louis. Over the course of the Gossip Girl series, which love interest did NOT consider proposing to Blair?
24Before they played a couple on-screen, which two Gossip Girl actors playing these characters were home schooled together as kids?
Did you know that Penn Badgley, who plays Dan in the series, was named after the tennis ball company Penn? Or that Taylor Momsen, who played Jenny, first appeared in acting as Cindy Lou Who in How The Grinch Stole Christmas? This next one is pretty crazy. Who knew that actors and actresses had lives outside their popular shows, right? Before they played a couple on-screen, which two Gossip Girl actors playing these characters were home schooled together as kids?
25So, last but not least, who is Gossip Girl?
Throughout the entire series, viewers are left wondering what Gossip Girl’s true identity is. Many misleading hints are dropped along the way. Gossip Girl makes a mess of everyone’s lives time and time again. The secret blogger’s identity is finally revealed in the series finale, “New York, I Love You XOXO,” after Nate and Sage try to figure out who it is, but fail. The revelation of the identity was fairly controversial and disappointed many fans. So, last but not least, who is Gossip Girl?