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140 Gossip Girl Trivia Questions, Answers, and Fun Facts

How much do you know about Gossip Girl? This category is for trivia questions and answers related to Gossip Girl (Television). Each one is filled with fun facts and interesting information.
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1 What is Nate's surname?
Answer: Archibald

Nate Archibald was played by Chace Crawford. Nate had a lot of charm when it came to the ladies as he shared relationships with Serena, Vanessa and Blair. He even shared a kiss with Jenny. Nate went through some rough patches throughout the seasons including turning his father in to the police, losing all his money and having to live in a sleeping bag in his house. But everything got better for him in the end, he ended up working at the "New York Spectator" with talks of him running in an election. We last see him getting on a private plane.
  From Quiz: Who's Who in 'Gossip Girl'?
2 In the beginning of the episode, Jenny is on the phone with a colleague. What nationality did she refer to when putting down the phone?
Answer: Italians

She was talking about the buyers for Bloomingdales' meeting that would be on that day. Elenor Waldorf put her in charge of the designs.
  From Quiz: "Gossip Girl"-Season 2 Episode 8
3 At the beginning of the episode, who does Dan save from being hit by a cab?
Answer: Serena

Dan had actually saved Serena from a cab Thanksgiving the year before the majority of this episode actually takes place. While saving Serena, the pie Dan had bought got destroyed.
  From Quiz: "Gossip Girl"- "Blair Waldorf Must Pie!"
4 Episode 11: 'Roman Holiday' What is the name of Blair's father's gay lover?
Answer: Roman

Blair's father, Harold, brings Roman along with him to the house for Christmas holidays. Neither Blair nor her mum are very happy to see them.
  From Quiz: 'Gossip Girl' - Season 1 - Part 3
5 Episode 6: 'The Handmaiden's Tale' What is the name of Dan's childhood friend?
Answer: Vanessa

Vanessa is Dan's childhood friend, and now that she has returned, Dan is confused between her and Serena as he doesn't know whom to choose.
  From Quiz: 'Gossip Girl' Season 1 - Part 2
6 Episode 1: 'Pilot' What is the name of the 'It' girl who returns to the Upper East side from boarding school?
Answer: Serena van der Woodsen

Everyone finds out about Serena's return back to Manhattan from the from the Internet site of 'Gossip Girl'. No one has any idea about her identity, but she always knows everything about everyone and people love to gossip about the things she posts on her site, as they are almost always true.
Serena returns to the Upper East Side because of her younger brother Eric, who is admitted in the Ostroff center because he attempted suicide.
  From Quiz: 'Gossip Girl' Season 1 - Part 1
7 Why isn't Serena happy about her date with Dan?
Answer: He tries to be too fancy

Dan tries to impress Serena with a limo and a fancy restaurant, but that's not what Serena wants. She wants things different from what her life is like. She thought that going out with Dan would bring that but she was wrong. She lets Dan know that fancy is not what she wants, so Dan takes her to a pool hall where she enjoys herself a little more.
  From Quiz: "Gossip Girl" - "Dare Devil"
8 Who is interested in carrying Eleanor Waldorf's line in their store?
Answer: Henry Bendel

Blair's mother, Eleanor, returns from Paris at the beginning of this episode with the news that Bendel wants to carry her line, Eleanor Original. She thinks that this could be their biggest shot.
  From Quiz: "Gossip Girl" - "Bad News Blair"
9 It's Ivy Week at Constance Billard and St. Jude's. What are the girls and guys in charge of respectively?
Answer: The Friday night mixer and ushers for the representatives

It's tradition that the Constance Billard girls are in charge of the Friday night mixer while the boys of St. Jude's were interviewed to find out who would escort which Ivy League representative.
  From Quiz: "Gossip Girl" - "Poison Ivy"
10 The day after Blair's Kiss on the Lips party, another party is held by the upper class. Where does Sunday Brunch take place?
Answer: The Palace

When it comes to Manhattan Upper East Side, what is never bound to change is that as soon as a social event is done - Blair's Kiss On The Lips Party - another one is right on the way: Sunday Brunch at The Palace.
  From Quiz: "Gossip Girl" - "The Wild Brunch"
11 Who does the voice of Gossip Girl?
Answer: Kristin Bell

Kristin Bell has a role on the NBC hit series "Heroes". She also played the title character on "Veronica Mars".
  From Quiz: "Gossip Girl" - Pilot Episode
12 Why was Serena's brother, Eric, in the hospital?
Answer: he tried to commit suicide

Eric's mom told everyone that he was visiting his aunt in Miami to avoid embarrassment, which aggravated Serena.
  From Quiz: "Gossip Girl" - Pilot Episode
13 What is Blair's surname?
Answer: Waldorf

Blair Waldorf was played by Leighton Meester. Blair went through so much during the show including, losing her virginity to Chuck, the on-off relationship she went on to share with him, the car crash, getting married to a prince and her miscarriage plus her very quick wedding with Chuck. We last see Blair at the wedding of Dan and Serena with her family including her husband Chuck and her son, Henry.
  From Quiz: Who's Who in 'Gossip Girl'?
14 Who was in the bathroom when Jenny opened the door?
Answer: Nate

Nate has been living with the Humphreys because his house is being seized for not being paid. He was living in his living room while sleeping in a sleeping bag. When Dan found out, he invited Nate to stay with him and his family for a while.
  From Quiz: "Gossip Girl"-Season 2 Episode 8
15 In which season finale does Chuck finally say "I love you" to Blair for the first time?
Answer: Season two

When Chuck announces that he loves Blair, she asks him to say it twice. He then says it over and over counting the amount of times he says it. The credits come on after the fifth time.
    Your options: [ Season three ] [ Season two ] [ Season one ] [ Chuck never said "I love you" to Blair ]
  From Quiz: "Gossip Girl" Seasons 1-3
16 What is Nate's full name?
Answer: Nathaniel

Chuck often calls Nate his full name, too. Later that episode, Nate walked in his house and found his father lying on the ground.
  From Quiz: "Gossip Girl"- "Blair Waldorf Must Pie!"
17 Who says this quote? "Was she just about to tell me she loved me?"
Answer: Dan

This was when Nelly Yuki was about to profess her love to Dan, before she saw Serena and got scared, which caused her to run away.
  From Quiz: The Goodbye Gossip Girl
18 Episode 12: 'School Lies' Who says the the key to the swimming pool was his to save Blair from the headmistress?
Answer: Nate

Nate tells the Headmistress that he broke into the swimming pool in the night because he thinks it was Blair. He does that to save her career. But he later finds out that Blair was just keeping the key for someone else.
  From Quiz: 'Gossip Girl' - Season 1 - Part 3
19 Whom does Nate mistakenly kiss at the ball, thinking she was Serena?
Answer: Jenny

Nate tries to confess to Serena that he still has feelings for her but ends up telling that to Jenny instead as she was wearing Serena's mask.
  From Quiz: 'Gossip Girl' Season 1 - Part 2
20 What is the name of the party Blair organises in the first episode?
Answer: Kiss on the Lips

Blair organises the 'Kiss on the Lips' party and doesn't invite Serena. But Serena ends up coming anyway with Dan to help his sister, who was getting molested on the rooftop of the party by Chuck Bass.
  From Quiz: 'Gossip Girl' Season 1 - Part 1
21 How does Jenny manage an invite to Blair's sleepover?
Answer: Serena bails out

Because Serena drops out of the sleepover, her unhappy BFF looks for a replacement for her and Jenny just happens to be perfect. Of course the sleepover ends up being more of an initiation for Jenny than a bunch of friends getting together for popcorn and pillow fights.
  From Quiz: "Gossip Girl" - "Dare Devil"
22 While throwing a boys' weekend, Chuck and Nate are visited by an old friend. What is his name?
Answer: Carter Baizen

Carter Baizen is a former student of St. Jude's. He used to be a party animal, like Chuck, but claims to have changed his ways after traveling the world and filming documentaries. Nate thinks he's cool, Chuck, on the other hand, is suspicious of him.
  From Quiz: "Gossip Girl" - "Bad News Blair"
23 What school does Nate's father want him to attend?
Answer: Dartmouth

The keywords to the Captain's future for Nate: Dartmouth, law school, Blair. Nate tries to reply that maybe he has his own plan, but the Captain doesn't seem that interested in listening to it.
  From Quiz: "Gossip Girl" - "Poison Ivy"
24 Who does Serena visit at the beginning of this episode?
Answer: Eric van der Woodsen

Serena, former-bad-girl-turned-into-SS aka Saint Serena, is filling her brother Eric in on how Dan ended their date with a wave. Eric is kind of stunned and claims that he definitely "wouldn't have taken Dan for a waver".
  From Quiz: "Gossip Girl" - "The Wild Brunch"
25 At the beginning of the episode, Serena van der Woodsen is seen returning to Manhattan from boarding school. What happened to make Serena leave and go to boarding school?
Answer: she slept with her best friend's boyfriend

We soon find out that Serena has betrayed her best friend, Blair Waldorf, by sleeping with Blair's boyfriend, Nate Archibald. She couldn't face Blair after what she had done and chose to leave and go to boarding school.
  From Quiz: "Gossip Girl" - Pilot Episode
26 Who is (or was) Serena's best friend?
Answer: Blair

The first day Serena returned to school, Blair made it obvious that things were not the way they used to be. She refused to give Serena an invitation to her party, Kiss on the Lips.
  From Quiz: "Gossip Girl" - Pilot Episode
27 Tell me who I'm talking about. She's blonde, young and her surname is Van Der Woodsen.
Answer: Serena

Serena Van Der Woodsen was played by Blake Lively. Serena was the first character that we saw a Gossip Girl blast being written about. She had a very hard time during the show as she was drugged, had to come to terms with the fact that she had played a part in a mans death and deal with her mother's illness which turned out to be the result of her father giving her medication to make her feel the symptoms of being ill. She was one half of the 'will they? Won't they?' couple, the other half being Dan. The last time we see her is when she is getting married to Dan.
    Your options: [ Lily ] [ Serena ] [ Lauren ] [ Lola ]
  From Quiz: Who's Who in 'Gossip Girl'?
28 What does Chuck want from Blair?
Answer: He wants her to say "I love you" to him

In the previous episode, Blair played with Vanessa in order to get to Chuck. In the end, Chuck wanted Blair to admit that she loved him before he gave in.
  From Quiz: "Gossip Girl"-Season 2 Episode 8
29 Who gets pregnant in the third season?
Answer: Dorota and Georgina

We find out Dorota is pregnant in "The Treasure of Serena Madre" and she delivers her baby in the finale. We also find out Georgina is pregnant in the finale.
  From Quiz: "Gossip Girl" Seasons 1-3
30 After they were uninvited from the Waldorfs' Thanksgiving dinner, what did the van der Woodsen household plan on eating for dinner?
Answer: A raw pumpkin and a duck

Serena told Dan that she and her family were going to have raw pumpkin and a duck, and he insisted that they join his family for dinner. He also mentioned that his family had a very large table in their dining room.
  From Quiz: "Gossip Girl"- "Blair Waldorf Must Pie!"
31 What does Chuck find out Blair did on New Year's?
Answer: She slept with Jack Bass

Gossip Girl reveals that Blair slept with Jack, and Blair in turn finds out that Chuck slept with Vanessa.
  From Quiz: The Goodbye Gossip Girl
32 Episode 13: 'A Thin Line Between Chuck and Nate' Who gets spotted buying pregnancy tests?
Answer: Serena

Serena goes to buy pregnancy tests for Blair because she is scared that Blair became pregnant when she lost her virginity to Chuck. Gossip girl reports this on her website and soon everyone thinks Serena is pregnant.
  From Quiz: 'Gossip Girl' - Season 1 - Part 3
33 Episode 7: 'Victor/Victrola' What does Chuck want to invest in?
Answer: A strip club

Chuck decides to invest money in a strip club to impress his father and make him proud. Bart is sceptical of the idea at first but then agrees as he wants to test his son's potential.
  From Quiz: 'Gossip Girl' Season 1 - Part 2
34 Episode 2: 'The Wild Brunch' Whom does Serena have sex with before leaving town?
Answer: Nate

Nate is Blair's boyfriend and Serena feels really guilty about having sex with him because he was her best friend's boyfriend, so she leaves town. Blair tries to seek revenge against Serena as soon as she finds out about this.
  From Quiz: 'Gossip Girl' Season 1 - Part 1
35 Why doesn't Serena attend Blair's annual sleepover?
Answer: It's her first real date with Dan

DAn and Serena have attempted their first date a couple times and are determined to get one right. Blair is not happy about Serena's absence, but she does approve of her friend's reason for it.
  From Quiz: "Gossip Girl" - "Dare Devil"
36 What actor does Chuck claim Carter looks like when he's between movies?
Answer: Matthew McConnaughey

Sebastian Stan (the actor who plays Carter), is best known for his role as Chase Collins in "The Convenant", which also starred Chace Crawford. Crawford has called Stan his best friend.
  From Quiz: "Gossip Girl" - "Bad News Blair"
37 Which rep does Dan want to be an usher for?
Answer: Dartmouth

Dan attends the interview in order to get the usher position for the Dartmouth rep; he claims Dartmouth is his dream and that he shares Dartmouth's principles of integrity, responsibility and consideration thanks to St. Jude's and his parents who sacrificed all to let him attend that privileged high school.
    Your options: [ Dartmouth ] [ Harvard ] [ Princeton ] [ Yale ]
  From Quiz: "Gossip Girl" - "Poison Ivy"
38 What kind of dress does Blair give Jenny to extend friendship to her?
Answer: an Eleanor original

Jenny stops by Blair's, seeking advice and friendship. After discovering that Jenny is the sister of Serena's mystery man, Blair allows her to enter her inner circle by giving her an expensive dress as a gift. An Eleanor Original, also known as "the uniform of B's private army".
  From Quiz: "Gossip Girl" - "The Wild Brunch"
39 Why did Serena return to Manhattan from boarding school?
Answer: her brother attempts suicide

Serena rushes home when she finds out that her brother, Eric, attempted suicide. Serena's mother, Lily, tries to hide Eric's absence by telling everyone that he's visiting his aunt in Florida.
  From Quiz: "Gossip Girl" - Pilot Episode
40 Who was Blair's boyfriend?
Answer: Nate

Serena was intimate with Blair's boyfriend, Nate. That is the reason why Serena left. When she returned, Nate tried to hook up with Serena again, but she turned him down.
  From Quiz: "Gossip Girl" - Pilot Episode
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