How the f*** did the Gossip Girl writers take us on such a roller coaster?

How did Jenny and Chuck go from an attempted SA in episode 1 to Jenny willingly swiping her V-card with Chuck in the finale of season 3?

How did the relationship between them evolve to this degree?

What happened in Season 2?

Well that’s where power shifts, emotional parallelism, and normalization started taking over.

The dynamic of Chuck and Jenny gradually evolved from predator versus protege to two outsiders with messy arcs in their own individual rights. Chuck began softening as a character while Jenny began growing colder and harder.

In Season 2, Chuck’s storylines revolved around believing his father actually died, grappling with the traumatic guilt of believing he killed his own mother in childbirth, and feeling overly consumed with trust issues about every person around him.

His trust issues even ended up hurting Blair at the beginning of Season 2 because he was so scared of committing to her or showing her any signs of vulnerability.

He ditched her after they made plans to spend a summer of love together in Europe. She jetted off to Europe while he stayed in New York hook up with different girls because he felt too scared of building a serious relationship with Blair.

His emotional immaturity was stunting him in all areas of his life, and he was feeling the pain of that. As far as Jenny goes, she became Queen Bee in Season 2, fully dethroning Blair Waldorf after Blair chose her to be her successor.

She went through a major evolution feeling more confident in her talent as a fashion designer, feeling more independent from her father‘s parenting style, and even feeling more romantically adventurous pursuing a connection with Nate Archibald.

It’s abundantly clear that Jenny and Chuck were both growing in Season 2, however, they were growing in opposite directions. Chuck was becoming more human. Jenny was becoming more ruthless. They built a very strange parallel journey because of it.

But the writers of Gossip Girl began placing them scenes where their motivations were overlapping. They both expressed their desire to lean into deep ambition in Season 2.

Chuck wanted to step up and inherit a position on the board following his father‘s death. Jenny wanted to carve a name for herself in the fashion industry beyond Waldorf Designs where she had been working as an intern. Both Chuck and Jenny felt a lot of loneliness in Season 2.

When Blair insisted Chuck opened up to her with vulnerability by saying those three little words made up of eight letters, Chuck simply wouldn’t say it. He was scared of putting his heart on the line.

Jenny, on the other hand, was interested in pursuing a relationship with Nate, but her older brother Dan sabotaged their connection when he found out what was going on behind his back.

Nate was temporarily living with the Humphrey family, but Dan kicked him to the curb in order to keep him far away from Jenny. Both their relationships crumbled, so to say and were both super lonely in Season 2 is an understatement.

Additionally, they were both feeling frustrated about things in their family life. Chuck felt like he was still disappointing his father, even though his father had “passed away.”

Jenny felt like her father was constantly controlling her and making her life a living hell. From the viewer’s perspective, Chuck and Jenny started being seen as two complicated antiheroes.

The second season of the show normalized the two of them sharing space as characters, even though they weren’t inherently close.

Check back for more analyses of Chuck and Jenny on LoveTravelBeauty.