The Fantasy of Serena van der Woodsen

Part Three of Three

[This profile contains discussion of suicide and sexual assault.]

The season opens with Serena still in California, working on the set of The Beautiful and Damned. California Serena is thriving in bright oranges and yellows, sunny colors for the summer weather. For example, she wears this pink-and-yellow printed dress in episode one, paired with yellow and orange necklaces. Big necklaces, says Daman, are season five Serena’s new “statement piece. . . . We’ve toned down the clothing and amped up the jewels” (“5 Years”).

Serena has a potential new mentor in one of the movie’s producers, Jane, and a jealous supervisor, Marshall. When Serena finally meets with Jane, she learns that Marshall took credit for the comparison she wrote at the beginning of the summer. Jane asks Marshall to give Serena more responsibility, and so he gives her his entire task list, sure she won’t be able to finish it that day. Her last task is getting the film’s star some medical marijuana—marijuana, she soon learns, that he isn’t allowed to have or the movie will shut down. 

When she confronts Marshall, he accuses her of showing him up. “I need this job more than you do, okay?” he says. “I pay for my life. . . . You do one lap around this party, you’ll get ten job offers. You weren’t even looking when you found this one. In two weeks, when you’re at college, will you even look at this as anything more than that thing you did that summer?” Guilted, Serena offers to clean out her desk.  

The next day, when she goes to get her things, Jane offers her a job with her production company; she sees something in Serena that she can’t yet see herself—a talent, a purpose, that Serena’s never had before.

Serena’s color palette carries over to an unexpected character: Ivy Dickens, now auditioning for roles and living with her boyfriend, Max, in Los Angeles. Serena runs into Ivy at a café and, still believing her to be Charlie, convinces her to come back to New York. Caught in Carol’s lie, Ivy quickly cuts ties with Max and moves out (5.2). In this episode, Serena wears a gray striped tank and floral-print skirt, topped with a coral blazer and dangly earrings. Professional Serena is back, a blazer the solution to any outfit. Ivy keeps things more casual but picks up Serena’s coral tones in her jeans and hat. 

Serena and Ivy return to the city in episode three, and Serena helps Jane set up her New York office. She’s flourishing in her new role, still wearing her sunny color palette—even convincing the reclusive Daniel Day-Lewis to consider one of their scripts. That is, until Dan’s first novel, Inside, is published, the characters based on his friends and family (5.4). Before Blair and Serena read it, both assume Serena is the focus, as she was in Dan’s New Yorker story. “Every girl needs to be knocked off her pedestal a little,” Serena jokes. “Can’t handle that kind of pressure.”

And knocked off her pedestal she is. Claire Carlyle is the real star of Dan’s book, while Sabrina von Sloneker is a “dreamy blonde with . . . legs” for which “everything comes easy.” She’s “glamorous, sexy, beautiful” but also “selfish, insensitive, shallow.” She’s Dan’s fantasy wrapped around the reality he could never handle, a muse undone. To quote Taylor Swift, “Darling, I’m a nightmare dressed like a daydream.” The cherry on top is “Sabrina,” the name her crush Julian once dismissively called her.

Serena, of course, is furious with Dan. “In high school, you were the only one who saw me for who I really was or who I wanted to be,” she tells him. “You helped me be somebody that I was more proud of. Do you even remember the girl you fell in love with? Or just that she got so drunk on Thanksgiving that she got grazed by a taxi . . . or slept with not one but two of her professors?” Serena’s past continues to follow her, now into her work life. Her fellow assistant believes she’s Sabrina, Daniel Day-Lewis drops their project, and Jane says she can save her job by getting the film rights to Inside.

The next episode, Serena has dropped her California color palette and reclaimed her sparkly pieces—as if she’s realized she can’t reimagine herself, can’t escape the image that others have created of her. To breakfast with Dan, Serena wears a silver-sequined teal shirt, striped skirt, and teal jeweled earrings. There, she fake apologizes to Dan for her reaction to his book, hoping he’ll agree to let Jane’s company produce the movie. Though they do ultimately reconcile and Dan does give her the rights, Serena never quite receives what she wants. Dan, now in love with Blair, remains unconvinced that Serena is the love of his life—as he is for her.

In episode six, Serena learns that Jane wants to turn Inside into the next Social Network—and “Zuckerberg” Dan in the process. Worried, Serena asks Jane’s old friend—newspaper mogul Diana Payne—for help. Diana reminds Jane of their shared history to convince her to drop the film. Considering that Diana is later revealed to run a brothel, I’m inclined to think Jane was once a sex worker, her past trailing her just like Serena’s trails her. Even their outfits mirror each other’s: both in one-shouldered dresses and dangly gold-chain earrings, Serena’s teal and Jane’s purple and black.

Diana, however, gets just what she wants: she convinces the now-jobless Serena to write a blog for her newspaper, The Spectator. Through her own writing, Serena can take back her narrative from Gossip Girl and Inside.

Outside the Spectator offices, Serena meets Ivy’s old boyfriend, Max—in the city for a job interview. After a flirty chat, and at Diana’s encouragement, she invites him to a production of Sleep No More. While Serena waits outside, believing Max has stood her up, Diana secretly sends Max in, telling him that Serena is wearing a “beautiful gold dress.” The actual girl in the gold dress? Ivy, of course.

Max slowly pieces together Ivy’s deceptions, all while beginning to date Serena. He even shows up at the penthouse the night of CeCe’s Studio 54 party, the Rhodes women dressed in seventies-inspired metallics and sequins. Serena herself is in a giant gold necklace and draped gold dress, as if she’s finally wearing that “beautiful” dress that Max was looking for. When Max tries to convince the family that Ivy is not Charlie Rhodes, Ivy says that Max is blackmailing her with a sex tape; she is worried, she says tearfully, that he will do the same thing to Serena. It’s a perfect lie: tinged with the threat of revenge porn, sympathetic to Serena, whose past is constantly used against her.

After her “close call” with Max, Serena reflects on her dating history. As she tells Dan: “I thought I changed my ending by getting the job with Jane or this blog, but the truth is, I’m still making horrible decisions in my love life.” Dan advises her to look through Gossip Girl, and when she does, she realizes that she never got things “right” before or after Dan.  

Blair, meanwhile, is about to marry her prince, Louis. When he suspects that Blair and Dan are having an affair, Serena covers for them, saying that she and Dan are secretly dating. Louis believes her and Serena gets what she wants—an excuse to stay close to Dan until Blair’s wedding.

Bubble Episode

I had many options for Serena’s bubble episode, but I kept coming back to 5.13, “G.G.” I felt odd, at first, choosing Blair’s wedding episode for Serena’s profile, but in many ways, the episode is as much Serena’s as her best friend’s.

Let’s start with the opening scene: Serena’s first and only dream sequence. Blair often dreams herself into Audrey Hepburn movies, but Serena imagines herself as a different star, the one Maureen once compared her to: Marilyn Monroe. In her dream, Serena lip-synchs to Marilyn’s “Diamonds Are a Girl’s Best Friend”; the men dancing around her include Louis, Nate, Chuck, and Dan. When Dan sees Blair, dressed as Holly Golightly in Breakfast at Tiffany’s, he breaks away from the group. Serena tries to pull him back, but he escapes her grasp, ascending the stairs to Blair.

Serena’s costume is not an exact replica of Marilyn’s but a high-fashion assemblage of its components: pink strapless gown, pink opera gloves, and piles of diamonds. Tom and Lorenzo wrote an excellent analysis of the gown and its legacy, and unsurprisingly, the dress is loaded with sexual symbolism:

 It’s a gown that speaks of sex and femininity even as its wearer sings a song about money and security. We could get into the long history of pink in costume design as a coded color for femaleness (or as an even more coded reference to the vagina). We could talk about the history of the opera glove on-screen and how it was a shorthand for a sexually available woman. . . . Suffice it to say, Marilyn is practically clothed in over a half century of tropes denoting female sexuality here.

The men are dressed identically in white tie, as they were in the original scene. But unlike in the original, the men aren’t just a bunch of random hunks—they’re men whom Serena knows, some of whom she’s dated. In Serena’s subconscious mind, the men in her life are there to worship her, to desire her, to serve her; no man has ever wanted Blair over Serena, especially not a man as important to her as Dan. He’s supposed to choose the Marilyn, not the Audrey (funny, considering Marilyn was Truman Capote’s choice for the role of Holly).

Serena wakes in a silky platinum-colored nightgown and robe, almost blending back into her sheets and the dream she’s still absorbing. It’s the morning of Blair’s wedding, and she changes into a striped gray-and-pink sweater and pink printed dress—the touches of pink calling back to her dream and hinting at the day ahead. As Serena stands at the top of the stairs, looking down the excited Louis, Dorota tells her that one day she’ll find a man who loves her as much as Louis loves Blair—and then Dan walks in. Unlike in the dream, neither ascends or descends the stairs—Dan only stares up at her, high on her pedestal, as he did on their first date.

Serena changes into her maid of honor gown and matching fascinator—pale pink, like the lesser bridesmaids’ dresses, but longer to show her status. The color matches the wedding’s flower, peonies, but also reminds the viewer of Serena’s dream.

Seeing Blair’s doubts over her wedding, Serena tries to convince her that she should be with Chuck—that Chuck is to Blair as Dan is to Serena, that they always come back to each other. Even after Gossip Girl posts a video of Blair declaring her love for Chuck, Blair goes through with her wedding. Serena, however, doesn’t give up on Dan, telling him she still loves him: “Always have, always will.” Dan doesn’t have an answer for Serena and instead helps Blair escape the reception—going up some metaphorical stairs, if you will.

By episode fifteen, Blair is playing Cupid, her ill-fated marriage to Louis having sapped any romance from her life. When both Dan and Serena tell her that their last good Valentine’s Day was with each other, Blair sets them up. She cancels their plans at the same restaurant so they’ll eat together, even hires an older couple to tell them how cute they are. Despite Dan’s rejection at the wedding, Serena is still in love with him, her interest apparent in her Humphrey plaid sweaterdress, much like something she would’ve worn in season one.

Even the fake couple calls back to season one Derena (and, in my opinion, When Harry Met Sally . . .): the man in an argyle sweater with a plaid shirt, the woman in gold jewelry. Though Dan and Serena soon figure out Blair is behind their setup, they agree to attend Nate’s Come As You Were party with her—the dress code is their high school uniforms.

Serena, of course, wears her plaid skirt and loose tie with a white tank and sparkly striped cardigan. Still, the pieces aren’t enough to rekindle old love—at the party, Serena walks in on Dan kissing Blair.  

Though she’s initially resistant to Dan and Blair dating, Serena gives her blessing in episode sixteen. By then, she has other things to worry about: When CeCe dies, her family finally discovers that Charlie is Ivy and that Carol’s real daughter, Lola, also lives in the city. Not only that, but Georgina has passed Gossip Girl’s laptop to Serena, encouragement to take over the site rather than waste her time on her flailing Spectator blog.

These two stories intersect when Serena uses Gossip Girl to divert attention from herself and anoint Lola as the “new Serena” (5.19). As Blair reminds her friend, the first Gossip Girl post was Serena in a wet white dress: “You didn’t really become Serena van der Woodsen until you got naked on that aircraft carrier. . . . A photo landed on Gossip Girl and that was it.” Never mind that Serena was fourteen at the time, never mind that she never consented to the post—Serena decides to use the same weapon with Lola, taking her to Kiki de Montparnasse for gifted lingerie. While her cousin tries on the “Serena” slip, Serena pulls the fire alarm and escorts her to the street.

Her plot backfires: Kiki asks Lola to model alongside Serena, then renames the slip from “Serena” to “Lola.” Suddenly, Serena feels her it girl status slipping away, and she writes another post saying Lola staged the slip photo. “Doesn’t she realize that there can only be one it girl on the Upper East Side? And that will always be Serena van der Woodsen.”

Indeed, Lola takes attention from Serena in every way—not just from the public but from her father. In episode twenty-one, Serena sees William having lunch with Lola; guess what, he’s Lola’s long-lost father. “All you ever did was avoid me,” Serena tells him later, “and then now when you find out about Lola, you just rush to be by her side.”

Serena has no interest in being a sister to Lola; she just keeps falling deeper and deeper into Gossip Girl land—until an intervention from Lola and Nate returns the laptop to its original owner. She slowly starts to get her “life and friends back”—but then Gossip Girl drops a post in episode twenty-three, a scan of one of Blair’s diary pages. Serena took the scans back when she was running the site, and now the original GG is using them against her.

In the finale, Serena is back to the color palette she wore at the beginning of the season, her first outfit an orange halter top, blue floral skirt, and beaded necklace. She’s received an invitation from David O. Russell to the Beautiful and Damned premiere—a chance to get back into the industry she loves. Blair, however, is furious over the diary posts; as revenge, she writes a fake one saying that Serena never read The Beautiful and Damned, and once it’s posted, Russell rescinds Serena’s invite.

After Blair kicks her out, Serena takes her own revenge: at the Shepherd divorce party (a nice tieback to the Shepherd wedding), she gets Dan drunk and spills cocktails on him. When they go to the bar to dry off, she convinces him that Blair has chosen Chuck, and they sleep together. After, Dan discovers that her phone camera was recording them and realizes she manipulated him into sex—neither the show nor Serena herself understanding what a huge violation of consent this is.

Serena’s dress is not gold (as it was the night she slept with Nate) or even yellow. No, she’s wearing bright blue, the same shade she wore to graduation, the day Gossip Girl labeled her “irrelevant.” Serena is still terrified of becoming irrelevant—to Gossip Girl, yes, but also to Dan, the person who once crafted a whole mythology around her. When Dan tells he doesn’t “know who [she is] anymore,” she’s devastated.

She takes one last shot at him, stopping by the loft in a coral trench, striped shirt, and sparkly skirt. She says she deleted the video, that there’s “nothing standing in the way of [them]” anymore. Dan, unsurprisingly, never wants to see her again.

Serena ends up on a train out of Grand Central, an inverse of her return in the pilot. This time, Damien’s fellow dealer joins her, handing over the little white baggie she requested. He starts to kiss her neck, tells her his name is Zeke. “I don’t care what your name is,” she replies, staring out the window.

Serena’s outfit, too, calls back to the pilot, a striped shirt in both scenes. The other components, however, are different—her coat bright coral instead of a muted brown, her bottoms a sparkly skirt instead of dark-wash jeans. She’s no longer interested in showing her friends and family she’s changed; there’s nowhere she’s headed, no one she’s going back to.

Season Six

Blair, Chuck, Nate, Dan, and Georgina spend the premiere searching for Serena—the latter two hoping to find an ending to Dan’s scathing new exposé, Inside Out. No one’s heard from Serena all summer, and the viewer’s only glimpse is a shot of her passed out on the train, her nose bleeding. They find “Sabrina” instead, hosting a wedding at her new boyfriend Steven Spence’s house in Poughkeepsie. Serena has given him her character’s name, her birthplace as Wisconsin, her alma mater as Vassar. As she tells Blair, she began the summer being revived by paramedics; she wants a “fresh start” with Steven—away from the city, away from her family and former friends. Even her dress is a shadow of who she once was—the palest yellow and white, trimmed with lace.

By episode two, however, she’s back in the city with Steven. He’s an older businessman, the wealthy owner of a “holistic health company,” with the power and influence to get her on the Central Park Conservancy board. Philanthropy is a new path for Serena, the one her own mother and grandmother took when they got a little older, a little less “wild.” Indeed, her entire wardrobe around Steven has taken on a more conservative, Lily-like tone: a pair of statement earrings or a statement necklace matched with a simple solid or printed day dress (the neckline perhaps a little lower or the fit a little tighter than Lily would choose, but similar all the same).

When Serena suspects Steven is cheating on her (and with Nate’s new love interest, no less), she tells Lily, who advises her not to make a scene at the conservancy gala. “Tonight is your entrée into adult society,” Lily reminds. “That’s the difference between being a grown-up and in high school.”

But guess who is in high school? Nate’s new love interest (yuck)—and Steven’s daughter. Yes, Steven hasn’t yet told Serena that he has a seventeen-year-old daughter named Sage. Even more disturbing, Sage acts and dresses quite a bit like the rebellious old Serena, giving even more meaning to Serena’s new maternal style.

Like Serena, Sage attends Constance, and like Serena, she pairs her uniform tie and skirt with a white T-shirt and layered necklaces, her minions imitating her in white tees and denim vests or moto jackets. They look as if Serena reigned at Constance, a little dash of Blair from their hats as headbands.

It’s decidedly creepy, Steven dating a slightly older version of his own daughter, and in episode four, the story becomes even more twisted. After Steven discovers that Serena and Nate once dated, they decide to share their sexual histories—Serena lying and saying the last man she slept with was Ben. Again, she’s dressed like Lily in an orange sheath and statement earrings, the scene reminiscent of the time Rufus and Lily made lists of their sex partners (2.19). One name on Lily’s list? Steven Spence. They slept together while Serena was still in grade school, Steven so wasted on alcohol and painkillers that he doesn’t remember until Lily reminds him.

Serena, unsurprisingly, is disturbed by the idea of sharing a partner with her mother, but Steven asks her to try to forget about it. She attempts to, both in memory and wardrobe. By the next episode, she’s done away with the Lily drag, dressing in a navy top with arm cutouts and a pink printed skirt. Steven is acting strangely, almost forgetting to invite her to Sage’s cotillion, and with a peep at the ring box in his briefcase, she finds out why: he’s planning to propose. He asks Lily for her permission, but with a little prompting from Blair, she says no.

“I knew you wanted someone,” Lily tells her daughter. “But let’s face it, Serena. You don’t have boyfriends, you have life rafts.” Lily takes her life rafts, Serena counters, and leaves her “to drown,” her primary example being marrying Rufus and making it impossible for her to date Dan.

Unfortunately for Serena, Sage also knows about her father’s proposal plan, and she’s obtained a copy of Dan and Serena’s sex tape. (Yeah, Serena didn’t delete it last season.) As Sage is presented at cotillion, the tape plays on all the screens. Blair is furious, likening the act to taking “Nate’s virginity on that bar when [she] still loved him.” Steven, too, is angry at Serena for lying and breaks up with her.

At the end of the night, all who’s left is Dan, bobbing through the water like the last life raft. He asks if she’s okay and takes her out for a burger, his bow tie, black shirt, and vest reminiscent of the night they attended cotillion together. Serena, however, looks nothing like that night, no gold in sight. She’s wearing a strapless navy and black-beaded gown, black statement earrings. Perhaps her gold gown was too tainted with memories of Ivy, perhaps she was trying to be more mature, stately—like Lily. Either way, the effect is strangely mournful, fresh from the loss of Blair and Steven; sparkling, just a little, at the possibility of Dan.

In episode six, Dan and Serena are friends again, Dan staying in Eric’s old room. Serena’s style has veered to season one or two: a chunky necklace, red cardigan, black top, gray skinny pants, and boots. Indeed, the entire episode is packed with season one and two Derena tropes: Vespas, pool, chocolate-covered strawberries, stuck elevators. While Serena can’t quite reconcile the Dan in front of her with the Dan who’s been publishing scathing chapters about his friends and family, she also can’t quite let go of the idea of being his perfect Serena again. “I feel like I did when I first came back to the city from boarding school,” she tells him before he kisses her, “when all I wanted was a fresh start.” But the thing is, Serena is always looking for a fresh start—with Steven, with Dan, with Ben. She just keeps running into herself, her past. 

Serena and Dan begin dating, having made up with their friends. They even invite them all to Thanksgiving at the penthouse (6.8). In the middle of dinner, Dan’s Serena chapter finally publishes: “Golden Girl Falls from Grace: A Faux Love Story.”

Serena is devastated by Dan’s dissection of her, even reads the following paragraph out loud to him:

Serena is nothing. She’s a golden shell. Give her love, and she’ll do anything you want. With daddy issues like these, it’s not hard to push the right buttons, and once you do, the most powerful girl on the Upper East Side has no power at all.

By the following episode, she’s decided to move back to California, to finally escape her past. “In Los Angeles,” she tells Blair, “nobody cares if I date the wrong guy. . . . I have the chance to reinvent myself.” She almost makes it, too, until she finds a chapter tucked in her plane reading: the other Serena chapter, the good Serena chapter.

Serena goes to Dan’s apartment, demands to know which chapter is real. Dan explains through flashback, a long-awaited look at that party where they first met.

Interestingly, flashback Serena is not too different from present-day Serena: she wears a multistrand necklace, sequined tank, and black cardigan; present-day Serena in a tweed jacket, dress, and similar multistrand necklace. Remember, too, that this is drunk-Thanksgiving era Serena—the Serena in a short green dress and leopard coat. It seems strange that flashback Serena would look so put-together, as if Dan is placing a contemporary lens over his memory.

He looks up at her as she stands at the top of the Waldorf staircase—as he did on their first date, as he did before Blair’s wedding. Always looking up at her, his fantasy, his inspiration for Gossip Girl. Serena is fine with Dan being Gossip Girl, even going so far as to call the blog a “love letter.” She would see it that way; after years of being brought to her highest highs and lowest lows by Dan’s writing, she finally has a work to point to that says she was the definitive center, the muse for it all.

Five years later, Dan and Serena marry, Serena finally descending the stairs, still encased in her golden shell—this time, the gold bodice of her wedding gown. She looks beautiful, happy, but says nothing. Blair and Jenny get a few lines, hints at their careers in fashion design; we even learn what Lola is up to. But Serena? Nothing, nothing about her work, her life—only her relationship with Dan.

I wish, sometimes, that the writers had let Serena stay on that plane. That five years ahead, she’s writing her own narrative—producing movies in Los Angeles or traveling the world. Instead, her shell is empty—free from her past and free from any future, too.

[Stay tuned for Chuck Bass’s profile on Thursday, 5/13.]

DP on GG

My partner, Daniel, spent 2020 overhearing episodes of Gossip Girl from various rooms of our apartment. He still doesn’t understand the show and he doesn’t care.

DP: (hearing William van der Woodsen) Is that a Baldwin brother?

CL: Yes.

DP: Steven?

CL: No, Billy, I think?