One of the great joys of settling in for an old episode of CW’s Gossip Girl is its soap-opera level of absurdity. While binge-watching the original series ahead of its splashy HBO Max revival (out on July 8), one experiences a sort of hypnosis, lulled into a candy-coated New York City.
It’s a dizzying place to be—where traveling from the Upper East Side to Brooklyn takes only seconds and entering each other’s penthouse apartments requires zero permission. Story lines are tossed aside without resolution or dragged on within an inch of their life. Everyone sleeps with each other and nothing (not even age) can stop Serena (Blake Lively) and Blair (Leighton Meester) from sipping dirty martinis at the Empire Hotel after class.
Witnessing Gossip Girl’s game of romantic musical chairs and its disregard for awkward optics is part of the fun. According to Vanity Fair’s Richard Lawson, that guilty pleasure element is missing in the show’s 2021 follow-up. “Gossip Girl is all about aesthetics, and while the 2.0 edition does make distinctive, perhaps even bold style choices, where’s the playfulness, the garish flourishes that helped give the 2007 edition its loopy camp?” he asks in his review.
With this query in mind, we honor the original series’ most outlandish story lines. (The whole Dan Humphrey arc is worthy of its own post.) Perhaps the revival’s creative team can jot a few notes.
The most forgotten story line (at least by the writers, anyway) is that of Rufus Humphrey (Matthew Settle) and Lily van der Woodsen (Kelly Rutherford)’s secret son. It’s revealed during season two that they secretly welcomed a baby as teenagers. However, Lily put the newborn up for adoption and kept his birth hidden from Rufus. After getting past the whole “you kept an entire child from me” thing, Lily and Rufus travel to Boston in search of their son, where the boy’s adoptive parents lie and say that he died in a boating accident. However, a college-age Scott (Chris Riggi) is actually alive—and poses as an NYU student to get closer to his birth family. The plot proves weirdly anti-climactic when Scott unveils his identity as Lily and Rufus’s son to the group. Alas, he’s never referenced again after the third season.
Speaking of shady paternity plots, who could forget the time that conniving Georgina Sparks (Michelle Trachtenberg) named Dan (Penn Badgley) as her newborn’s dad? The logistics of this scheme never made sense. When Georgina shows up at Dan’s Brooklyn loft very pregnant in the season three finale, it’s been nearly a year since these two shared a bed. Dan accepts that he’s the father of baby Milo—paternity test unseen. To top it all off, he hides the fact that he’s apparently a new dad from everyone in his life, for reasons that aren’t totally clear. This tiresome story arc drags on for several episodes, and even includes a fake DNA test so that Dan will sign Milo’s birth certificate. By the time Georgina reveals that the real father is a Russian man named Serge, viewers are all too happy to throw this baby out with the bathwater.
One of the ickier story lines to revisit is that of Dan and Serena romancing teachers. In the second season, Dan dates his high school English teacher Miss Carr (Laura Breckenridge). Season four sees Serena being courted by both her Columbia guest lecturer Colin Forrester (Sam Page) and former boarding school teacher Ben Donovan (David Call). The unethical power dynamics aside, these illicit affairs do nothing to drive the series forward, or foster affection for any of the parties involved. Serena’s dating web gets particularly tangled when one considers that her mother, Lily, got Ben sent to prison when she signed an affidavit falsely claiming that he raped Serena. (Season four is a true test for G.G. fans.)
Another of Serena’s more regrettable beaus is Gabriel (a pre–Social Network Armie Hammer). Fans may remember him as the seemingly dashing suitor who ends up running a Ponzi scheme under the guise of providing internet to underprivileged children…we think? Gabriel’s bait and switch is further complicated by the fact that Serena briefly believes the pair married during a drunken night in Spain. (It wasn’t a legally binding ceremony, naturally.) Apparently, fans could have gotten even more Gabriel on G.G. had it not been for the show’s “tough filming” conditions, as Hammer teased in a 2017 interview.
Not to harp on Serena’s little black book, but a season six arc in which she and Nate (exes themselves, by the way) date a father and his 17-year-old daughter, respectively, is chilling. Nate even continues to see his underage girlfriend after learning her age. The only mildly amusing thing to emerge from this whole arrangement are scenes of Serena going all Meredith Blake on her potential stepdaughter-to-be.
One of the show’s tried-and-true ways of ridding itself of a tired plot point or restless actor is just old-fashioned banishment. Throughout the series, characters expel people from the Big Apple as punishment for getting too close to their inner circle. This was most famously done at the end of season three when Jenny Humphrey (Taylor Momsen, looking to leave G.G. and tour with her rock band, the Pretty Reckless) is warned by Blair to never return to Manhattan after a regrettable tryst with Chuck (Ed Westwick). She does know that adolescent socialites can’t decide who gets to live on the island and who is voted off of it forever, right? Some characters worm their way back in after being outlawed, such as the omnipresent Georgina. Others are never heard from again (so long, Juliet!)
Those who’ve closely watched the courtships and nuptials of Meghan and Harry, Kate and William—or even Grace Kelly and the Prince of Monaco—will find Blair’s monarch marriage far-fetched. What starts off as a promising fairy tale between Blair and Prince Louis (Hugo Becker) quickly goes off the rails. At one point, a jealous Louis pays Chuck’s therapist to steer him toward madness so that Blair won’t fall in love with him. A few episodes later, Blair miscarries her and Louis’s child, only to have that traumatic event never brought up again. Did we mention that Blair and Louis’s royal reception is held at…New York City’s St. Regis Hotel? Yeah, this blink-and-you-missed-it marriage was best left in the royal rearview.
Another subject not expertly honed in the G.G. writers’ room is politics. In season three, Nate’s cousin Tripp (Aaron Tveit) launches a congressional campaign. Despite the potential for juicy story lines surrounding a high-powered family’s attempts to enter the political sphere, this story line is ultimately toothless. The most scandalous things to emerge from the campaign are a PG-13 extramarital affair between Serena and Tripp, and a planned stunt in which he saves a “drowning” man from the Hudson River. Tripp’s heroics give him a lead in the polls, but not before aspiring documentarian Vanessa (Jessica Szohr) captures footage of the man willingly jumping into the water.
No conversation about problematic papas would be complete without Bartholomew Bass (Robert John Burke), who is shockingly offed in Gossip Girl’s second season. Bart’s car-crash demise haunts his son, Chuck, as he tries to escape his father’s shadow and locate his long-lost mother. (After not one, but two women falsely identify themselves as Chuck’s mother, that story line oddly fades away.) But in a Shakespearean twist of fate, Bart is found alive and well at the end of season five. It turns out that he faked his death in order to keep his family safe from an evil business adversary. Bart’s return is short-lived, however, when he wrestles the reins of Bass Industries away from Chuck, and even plans to have him killed. Needless to say, these two never make amends and Bart topples off the side of a Manhattan skyscraper.
Gossip Girl has had some of the weirdest guest stars of any TV show—from Real Housewives (Tinsley Mortimer) to real mayors (Mike Bloomberg, musing on Gossip Girl’s identity in the series finale). Ivanka Trump and Jared Kushner even pop up at the Boom Boom Room, of course. Then there’s Oscar-nominated filmmaker David O. Russell, who hires Serena on the spot in season four simply because she’s read the F. Scott Fitzgerald book he’s adapting into a movie. In a single episode, Serena goes from fetching coffee on the set of O. Russell’s fictional film to single-handedly courting Daniel Day-Lewis for a project. The way she entices the famously picky thespian? Sending him a handwritten letter and a rosebush that only grows in Ireland.
The cast heads to college in season three, inspiring story lines about NYU dorm parties and final exams at Columbia. But the show burns through its collegiate plot points in record time, and sends characters straight into the workforce. Not only is college graduation never mentioned, but each 20-something reaches the top of their respective industries almost immediately. After getting an article published in The New Yorker while still a senior in high school, Dan becomes a best-selling literary genius before age 21. Chuck goes from owning a burlesque club in high school to running a billion-dollar corporation at 19. Nate takes over The New York Spectator newspaper with nary a byline to his name. And Blair succeeds her mother as head of Waldorf Designs without ever sewing a stitch.
No story line is as infuriating, tonally confusing, or utterly pointless as the “Who is Ivy/Charlie” mystery. It starts in season four when Carol Rhodes (Sheila Kelley), Lily’s estranged sister, hires an actor to pose as her daughter. Enter Floridian swindler Ivy Dickens (Kaylee DeFer), who pretends to be Charlie Rhodes (Ella Rae Peck) so that Carol can get her inheritance. This convoluted saga drags on all the way through season six, and ends with no real payoff, but about 12 regrettable twists. Anyone else remember Rufus dating Ivy, who he once thought was his step-niece?!
Choosing the most nonsensical Gossip Girl side character is no simple feat. But none evades logic quite like William Baldwin as William van der Woodsen, Serena’s absentee father. Every time this man is on screen, he’s inflicting evil. In season three, he prolongs his ex-wife Lily’s cancer diagnosis by supplying her with symptom-mimicking drugs. For some reason, William is allowed back into the family fold for season five, where he’s revealed to be both the uncle and father of Charlie, Carol’s daughter. And in the final season, William fakes a relationship with Ivy (who he once believed to be his niece) for the sake of reconciling with Lily. And. It. Works! In the series finale, Lily and William are arm-in-arm like the twisted Upper East Side power couple they were apparently destined to be.
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