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?

Chuck tried to SA Jenny in the pilot episode of Gossip Girl at the Kiss on the Lips party when she was just a freshman.

Then by the Season 3 finale, she willingly swiped her V-card with him. Same two people.

Same show. Same universe. How did we get from point A to point Z, point Z being in hell?

This is one of the strangest, darkest, most controversial arcs in Gossip Girl history.

Let’s break down exactly how this relationship evolved and how the writers low-key engineered it from the very beginning.

The dynamic between Chuck and Jenny started as the predator and the protégé.

Chuck was considered one of the shows earliest villains.

Of course, he wasn’t as evil as some of the other bad seeds like Russell Thorpe, Poppy Lifton, or even his own father Bart Bass.

But Chuck was pretty scandalous. Because let’s not forget the fact that he also tried to SA Serena in Season 1 as well, which means Jenny wasn’t the only girl to almost become his victim.

Chuck maintained his bad boy persona throughout Season 1 proving to be a bad influence on his best friend Nate Archibald, a disappointment to his father by showcasing his rebellious nature all the time, and a man whore who slept around without respecting any of the women he interacted with.

And then there was Jenny, also known as Little J. In Season 1, she was depicted as naïve, yet overly ambitious with an insatiable craving for higher status and acceptance.

She wanted to fit in with the rich and popular crowd at her school, but she knew she would never fully fit in with her father‘s budget. Growing up in Brooklyn while going to school on the Upper East Side made her feel like she constantly had to prove herself without enough money in her wallet to actually pull it off.

She desperately wanted to dress the part since all her classmates were wearing designer pieces from New York hotspots like Saks, Bergdorf, and Barney’s.

But maybe even more than that, she was desperate to date the part. She wanted a relationship with a high profile partner, who could help her skip the line toward popularity, and notoriety.

She proved that closer to end of Season 1 when she dated Asher Hornsby who was just using her to hide that he was secretly attracted to other dudes.

Early interactions between Chuck and Jenny were hostile, manipulative, and transactional.

Chuck was all about testing boundaries. Jenny was all about masking her desperation to climb the popularity ladder.

Interestingly enough, Jenny’s early storyline revolved around her desperate desire to become Queen Bee, similar to Blair Waldorf. And Blair happened to be her idol. Jenny looked up to Blair with pure awe and admiration. Yes, Jenny feared the wrath of Blair, but she also wished she could trade places with Blair because Blair was already actively everything Jenny was trying to become. Jenny was Blair’s protege.

Chuck was part of the gatekeeping system that internally made Jenny feel like she would forever be an outsider. There was no emotional intimacy between them, but their storylines orbited each other because Jenny wanted part of the world that Chuck had ownership in.

Not only was he playing the Upper East Side status game, but he was winning. The theme of their energy in Season 1 was that they were opposites. Predator versus protégé.

Chuck was a textbook predator, keeping his eye out for easy targets he could use and throw away, manipulate, and benefit from for his own selfish gains. Jenny was the protégé of Blair and her knowledge of social hierarchy is why she agreed to go up to that rooftop with Chuck in the first place.

Keep in mind that the romance between Chuck and Blair didn’t start blossoming until later in Season 1. So Jenny‘s decision to go to the rooftop with him had nothing to do with Blair.

We can only imagine that Jenny had an idealized belief that Chuck might’ve actually want to get to know her and possibly become her boyfriend, and that’s why she agreed to talk with him privately at the party.

Jenny wasn’t trying to get revenge on Blair when she made the decision because Blair wasn’t even a factor in Chuck’s life just yet. Jenny solely agreed to go to the rooftop because she thought it could lead to the opportunity of a legitimate relationship with one of the most well-known and wealthy boys on campus.

We all know just how terrible that night went and how toxic it really was. Jenny was nowhere near ready to do what Chuck wanted, and it’s safe to assume he wanted to go all the way.

He started applying pressure, he was applying it thick. Jenny continually rejected him, and when she had the opportunity, she privately texted her brother Dan Humphrey to ask for help.

Who knows what would’ve happened between Chuck and Jenny on the rooftop if Dan and Serena hadn’t burst onto the scene to rescue her.

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