1. New York, I Love You XOXO S6.E10

It was because of this episode that Chuck and Blair were able to avoid having Blair testify against him by getting married. Dan's identity as a Gossip Girl was also exposed in this episode, and Jenny was aware of this when she was exiled by Blair.

2. The Goodbye Gossip Girl S2.E25

High school came to an end in the Season 2 finale. We still have to wonder why Serena chose to attach her graduation tassel to her hair instead of just wearing her cap, but it somehow seemed fitting for her.

3. O Brother, Where Bart Thou? S2.E13 

The drama surrounding a death on Gossip Girl was comparable to that surrounding a wedding. In question was Bart Bass's funeral.

4. G.G. S5.E13 

Serena played Marilyn Monroe in the opening number, and Blair played Audrey Hepburn. They were surrounded by the men in their lives, but Serena lost Dan to Blair. It was unmistakably a metaphor for the remainder of the episode.

5. Double Identity S4.E02 

Season 3 ended with most of the main characters going their separate ways and trying to turn over new leaves. “Double Identity” proved that in the world of Gossip Girl, the more things changed, the more they stayed the same.

6. Last Tango, Then Paris S3.E22 

Serena and Dan stayed out late together, which made their relationships with their respective partners difficult. When Chuck thought Blair didn't want to pursue a relationship with him, he offered her an ultimatum and went looking for solace elsewhere.

7. Pret-A-Poor-J S2.E08 

Season 2 began Jenny’s journey to figure out who she really was. This episode in particular saw her start to let loose a little bit.

8. Woman On The Verge S1.E17 

Serena came face-to-face with her past in the form of Georgina. Georgina knew what happened to push Serena to decide to attend boarding school. She decided to blackmail Serena, and that led to Serena spiraling.

9. The Townie S4.E11

Season 2 marked the beginning of Jenny's quest to discover her true self. She particularly started to let loose during this episode.

10. Valley Girls S2.E24 

It was because of this episode that Chuck and Blair were able to avoid having Blair testify against him by getting married. Dan's identity as a Gossip Girl was also exposed in this episode, and Jenny was aware of this when she was exiled by Blair.