Can you answer all 25 of these questions about Serena van der Woodsen from Gossip Girl? Only diehard fans actually can.

1. Serena described the boyfriend she dated at the end of her freshman year. Who was he?

• The captain of the lacrosse team
• The captain of the swim team.
• The captain of the basketball team.
• The captain of the soccer team.

Serena admitted she dated the captain of the swim team, which is how she got keys into the school pool.

2. What was Serena’s drug of choice before she turned over a new leaf?

• Cocaine.
• Molly.
• Shrooms.
• Xanax.

Serena was down to snort tons of cocaine during her party days.

3. How old was Serena when she finally returned to New York City from her stint in boarding school?

• 15.
• 16.
• 17.
• 18.

Serena was 16 years old when the events of Gossip Girl first began, and the show started with her return from boarding school.

4. How many brothers does Serena technically have by the finale of Gossip Girl?

• One.
• Two.
• Three.
• Four.

Serena technically has three brothers by the finale. Eric van der Woodsen as her biological brother, Chuck Bass as her adoptive brother, and Scott Rosson as her half-brother.

5. Serena started an affair with a married man. What was his professional job title?

• Doctor.
• Professor.
• Chef.
• Politician.

Serena had no business dating Tripp van der Bilt because he was a married politician.

6. How is Serena related to Lola Rhodes?

• Her half-sister.
• Her cousin.
• Her half-sister-cousin.
• Her niece.

Serena and Lola share the same father. Lola’s mother is also Serena’s aunt and Serena’s mother is Lola’s aunt, making them half-sister-cousins.

7. Serena dated a photographer who displayed her photos throughout Time Square. Who was he?

• Aaron Rose.
• Antonio Rose.
• Alex Rose.
• Abel Rose.

Aaron was the charming photographer who loved snapping pics of Serena until their inevitable breakup since he was the non-committal type.

8. What motivated Serena’s return from boarding school?

• Eric’s self-unaliving attempt.
• Serena was failing out.
• Lily desperately missed her.
• Blair waged war against her.

When Serena found out Eric tried to end his own life, she returned home right away.

9. Serena dated one of her college professors at Columbia. Who was he?

• Cameron Forestor.
• Cory Forestor.
• Colin Forestor.
• Cleo Forestor.

Serena and Colin dated, even though he was her professor. The power dynamic was problematic for sure.

10. When Serena was partying with Georgina back in the day, they pretended to be alter egos with what names?

• Svetlana and Savannah.
• Aleah and Alara.
• Delilah and Dolores.
• Winnie and Winona.

Georgina and Serena would pretend they were Svetlana and Savannah whenever guys would try hitting on them.

11. Serena dated a con man who swindled wealthy Upper East Siders. Who was he?

• Gunner Edwards.
• Gavin Edwards.
• Grayson Edwards.
• Gabriel Edwards.

Serena’s relationship with Gabriel proved that she was lacking serious discernment.

12. Serena took Nate’s virginity while they were both drunk behind Blair’s back. It went down on a hotel bar at the Shepherd wedding. Who was a witness?

• Chuck Bass.
• Penelope Shafai.
• Nelly Yuki.
• No one.

Chuck admitted that he saw Serena and Nate hooking up that night from an upper angle.

13. Serena dated an older man with a daughter who was almost the same age as her. Who was he?

• Samuel Spence.
• Spencer Spence.
• Steven Spence.
• Stanley Spence.

Serena’s relationship with Steven was bizarre since she wasn’t ready to take on a stepmother role.

14. What name did Dan Humphrey use for Serena’s character persona in his book, Inside?

• Sabrina.
• Selena.
• Satina.
• Siena.

Dan’s novel about the Upper East Side was scathing, and he didn’t hold back with his criticisms of Serena, who he referred to as Sabrina in each chapter.

15. Serena had a short-lived fling with Ivy Dickens’ ex-boyfriend. Who was he?

• Martin Harding.
• Max Harding.
• Matthew Harding.
• Mason Harding.

Serena and Max liked each other, but it didn’t evolve to become anything serious.

16. Serena was caught purchasing a pregnancy test and it was publicized in a Gossip Girl blast. Who was she buying the pregnancy test for?

• Herself.
• Lily van der Woodsen.
• Blair Waldorf.
• Jenny Humphrey.

Serena was buying the test for Blair who was nervous after sleeping with both Chuck and Nate in the same week.

17. Serena tried to slyly film herself hooking up with someone for manipulation purposes. Who did she do that to?

• Dan Humphrey.
• Nate Archibald.
• Carter Baizen.
• Tripp van der Bilt.

Serena wanted to make Blair jealous, so she tried to record herself hooking up with Dan. But Dan caught her in the act and called her out for it.

18. Which university did Serena drop out of at the last minute?

• Harvard.
• Yale.
• Cornell.
• Brown.

Serena wasn’t interested in attending Brown, even though Lily really wanted her to move forward there. She dropped out last minute after initially enrolling in classes.

19. Someone spread a rumor about Serena having an STD. Who sent that Gossip Girl blast?

• Blair Waldorf.
• Juliet Sharp.
• Bree Buckley.
• Vanessa Abrams.

Juliet wanted to destroy Serena’s reputation, so she went for the jugular telling Nate and Dan they should get tested for STDs after sleeping with Serena.

20. Which job title does Serena land in Los Angeles?

• Production assistant.
• News anchor.
• Voice actress.
• Audio technician.

Serena got hired as a production assistant during her time in Hollywood.

21. One of Serena’s ex-boyfriends had a short-lived fling with her mother, Lily. Which one?

• Carter Baizen.
• Tripp van der Bilt.
• Steven Spence.
• Ben Donovan.

Steven is the guy who had a sexual history with Lily before linking up with Serena. Weird!

22. Who was Serena trying to get attention from when she started doing wild things in front of the paparazzi?

• Lily van der Woodsen.
• Dan Humphrey.
• Carter Baizen.
• William van der Woodsen.

Serena desperately wanted attention from Wiiam because she had severe daddy issues and abandonment issues.

23. Georgina Sparks tried to blackmail Serena with a secret. Which of the following secrets about Serena was actually real on Gossip Girl?

• Serena’s eating disorder.
• Serena’s involvement in Pete Fairmain’s overdose.
• Serena’s threesome at boarding school.
• Serena’s abortion from freshman year.

The only secret that really applied to Serena was her involvement in Pete’s OD, even though it wasn’t even actually her fault that he died.

24. Where did Serena first meet Damian Dalgaard?

• Ivy League Mixer.
• Boarding school.
• Chuck’s Victrola celebration.
• Lily & Bart’s wedding.

Serena and Damian first met while they were attending boarding school together, way before he started dating Jenny Humphrey.

25. Why did Serena end up in the Ostroff Center years after her younger brother, Eric, was admitted?

• She partied too hard with Georgina.
• She was arrested for a DUI.
• Juliet drugged her.
• She threatened to unalive herself.

Juliet drugged Serena as part of her revenge plot. Serena didn’t willingly do any of those drugs by herself.

How many of these questions did YOU get right? Let us know in the comment section.