When Serena Van der Woodsen was front and center. The de-facto lead of the show, her unexpected return to the Upper East Side triggered the series' events, even as her best friend, Blair, got more and more weight in the plot.
Throughout GG's six-season run, Serena's storylines mainly had to do with her inability to be alone, her constant need for attention, her jealous and competitive relationship with Blair, her troubled relationship with every member of her immediate family, and the men in her life, in whose plots she constantly inserted herself. Looking at the whole thing, it's easy to see a sad undercurrent to Serena's actions, making it clear she's more troubled than the show realizes.
She Never Finishes What She Starts
Over the course of the show, Serena embarks on a series of short-term projects that she never really ends. These include school, since she loses her spot at Columbia because of her antics, and a string of very high-profile jobs that, for one reason or another, she never seems capable of maintaining.
Perhaps it's because she never takes things seriously, or perhaps it's her constant need to search for whatever it is she doesn't have, which honestly borders on self-sabotage. Whatever the reason, Serena's life is a series of projects without any conclusive ending.
Her Constant Search For Stability And Purpose
Serena never really seems to know jobs she does take lack a clear path. She works at a mayoral election campaign, a PR firm, a movie set, and as a columnist in The Spectator. For a time, she even modeled. In other words, she goes from job to job, basically seeing what sticks.
In the same vein, her personal life is always characterized by a lack of balance. Her volatile relationships with lovers, family, and friends deprive her of any sense of real security. Serena is aimless, always struggling to find something in which she'll truly excel and belong to and never really achieving it.
Her Lack Of Aspirations In Life
What does Serena want, really? Chances are, she doesn't really know. Her many jobs attest to the fact that she has no clear goal in life. During her cotillion speech (the one she actually wrote), she states that she plans to graduate high school and take a year off to teach English in South Asia. That's actually a really noble and ambitious goal, one that she never seems to pursue after graduating Constance, which makes it seem like something she just wrote for the speech, rather than an actual plan.
Like many other characters in the show, Serena mainly seems to go with the flow, just seizing the moment and hoping for the best. This happy-go-lucky attitude can only last so long, though, and the time will come when she'll have no safety net to fall back on.
Her Past Regrets
Serena had a very troubled youth. She heavily abused both alcohol and drugs, which led to some of the darkest episodes in her teenage years. Her drunken affair with Nate while at the Shepherd wedding and the drug-fueled night she spent with Georgina and Pete Fairman, and which ended pretty badly, as fans of the show know, are both stains in her past.
The fact that a lot of these events are constantly weaponized and used against her contribute to her inability to properly let them go, as she's always afraid they'd be used against her in some future argument.
How Everyone Constantly Slut-Shames Her
And speaking of past events being weaponized, Serena spent the entire series being Her boyfriends were always brought into the arguments she had, and so did Blair, who took special pride in reminding her of her love life and putting her down for it.
While it's true that Serena didn't always have the healthiest of relationships, instead of actually helping her, those close to her seemed content with just reproaching and humiliating her for them. If there's any confirmation that the "Non-Judging Breakfast Club" weren't really friends, it's this one.
Her Increasing Insecurities
During the show's 100th episode, "G.G." Serena has a fantasy that features her channeling Marilyn Monroe, singing Diamonds are a Girl's Best Friend, and being showered with gifts and attention from all the men in her life. That is until Blair arrives, in all her Audrey Hepburn glory, and steals the spotlight away.
As the show progresses, Serena's insecurities only increase. Soon, it becomes apparent that her It-Girl persona is just an act to get people to like her and give her the attention she craves for. Serena loves being the center of attention and is willing to do everything to stay there. Whether she's launching a crusade against Gossip Girl or actually becoming Gossip Girl herself, Serena's fears and insecurities always get the best of her.
Her Troubled Relationship With Her Mom
To say Serena and Lily didn't always get along would be an understatement. They were both terribly immature and often acted without care or concern for the consequences. Lily always hid things from Serena and even manipulated her, thinking she knew what was best for her daughter. For her part, Serena enjoyed going against her mother's wishes, especially when Lily's deceptions came to light.
Their tortuous relationship often puts them at odds with each other. And while it's fair to say that Lily was a pretty terrible mother, Serena was no angel either, which made for an awfully poisonous mother-daughter dynamic.
Her Toxic Relationship With Dan
Serena always thought Dan was a better person than he really was. She often saw him as this morally superior overachiever and put him on a pedestal that he definitely didn't deserve, going as far as considering herself lucky that someone like him fell in love with someone like her. As a result, she held him in higher esteem than any of her other lovers and always came back to him, even after all the terrible things he did to her (and she to him).
Dan too put Serena above all others (except perhaps Blair, who he arguably ranked higher in his own chain of perfection) and refused to see her for who she really was, instead preferring the dream version he came up with. Time and again, the two hurt and mistreated each other, only to get back together out of some desire to recover the romanticized version of their relationship, which they had during their high school years.
Her Toxic Friendship With Blair
The argument of whether Blair and Serena calling themselves sisters. On the other, they deeply envied what the other had and were in constant competition, each trying to outshine the other.
While there's definitely real love between the two, the fact that they deliberately hurt each other because they know that, no matter how bad it gets, they'll always be there for one another, is the very definition of toxic.
Her Constant Attempts To Gain Her Father's Love
Serena was perpetually branded by her father's abandonment. She spends most of the series looking and chasing after him, desperately trying to reconnect and win back his love and . William, however, shows no real signs of wanting a relationship with her, often choosing his own well-being over her's.
Serena's abandonment issues are arguably at the center of all her problems. They're the reason why she refuses to let go, why she only sees herself as others see her, why she's terrified of being alone and why she ultimately settles for a man who always kept her at a distance, and whose approval she'll constantly have to work for. It's a sad, bittersweet ending for the girl who started the show as a walking ray of sunshine.