We've Finally Figured Out Why Serena van der Woodsen Always Had to Go (A Psychoanalysis of The Upper East Side's It Girl)

By Alexus Mosley

Serena van der Woodsen is the Upper East Side’s certified golden girl. She’s luminous, adored, down to Earth, and yet just out of reach. But beneath the glossy hair and enviable wardrobe lies a restless psyche that can’t sit still and face her problems. Serena isn’t just dramatic; she’s addicted to escape.

Every time responsibility creeps in, she bolts. Whether it’s to boarding school, another relationship, a different city, or a new persona. (Remember the time she skipped town to Poughkeepsie, New York, and started going by Sabrina?) It’s classic avoidance, dressed as boho-chic. Her charisma, free-spiritedness, and beauty mask an underlying fear of accountability.

Psychologically, Serena is the archetype of the anxious avoidant: desperate for love, yet terrified of intimacy. She thrives on the chase, the attention, the chaos, but once she’s caught, she self-sabotages. And when her self-sabotage manifests, rather than confront the issue head-on, she sees it as another cage for her to slip out of.

Still, that’s the secret to Serena’s allure. She embodies the fantasy of effortless freedom, even if it’s destructive. To watch her is to watch someone constantly reinvent herself, even at the cost of stability. Is she intoxicating because she reflects our own secret wish to run away from the messes we’ve made and be forgiven, again and again, simply because we shine when the light hits us?

Serena isn’t just the It Girl of Gossip Girl. She’s also the psychological portrait of what happens when privilege collides with perpetual escape. Beautiful, chaotic, unforgettable… and never fully at peace.