It seems like just yesterday Serena van der Woodsen stepped off a train in Grand Central Station. Alas, it has been nearly 15 years since that iconic opening scene kicked off one of the most popular teen soaps of the CW era. After nearly a decade off the air, Gossip Girl is back and she’s off Blogspot and on Instagram. 

Before we dive into a new era and muster the courage to look up "cheugy," we’re taking a look back at the show (based on the book series) that inspired it all. Here are our recommendations for our favorite Upper East Siders.  XOXO

For Serena van der Woodsen, We Play Ourselves by Jen Silverman

Serena, our charming "It" girl, has always struggled with other people’s expectations of her. Known for her party-girl past, she’s constantly trying to balance the person everyone wants her to be, and her love of the spotlight. For her, we’re recommending We Play Ourselves by Jen Silverman. 

In We Play Ourselves, Cass, a promising young New York City playwright, heads to Los Angeles to reinvent herself after a blistering public shaming. Working on a semi-documentary about a group of teen girls who have a Fight Club, she becomes increasingly troubled by how the teens are being manipulated in the name of art. When a girl goes missing, Cass must reckon with her own ambitions and ask herself: In the pursuit of fame, how do you know when you've gone too far?

For Blair Waldorf, What We Lose by Zinzi Clemmons

Blair Waldorf is a whip-smart striver who gives everything for what she wants. Blair loves to make big plans for herself and her loved ones, and though those plans often fall apart in devastating fashion, she always finds a way to get back up. For Blair, we’re recommending What We Lose by Zinzi Clemmons. 

In What We Lose, Thandi feels like an outsider wherever she goes, caught between being black and white, American and not. She tries to connect these dislocated pieces of her life, and as her mother succumbs to cancer, Thandi searches for an anchor—someone, or something, to love. Readers watch Thandi’s life unfold, from learning to live without the person who has most profoundly shaped her existence, to her own encounters with romance and unexpected motherhood.

For Dan Humphrey, Summer Fun by Jeanne Thornton

Dan Humphrey is “the ultimate insider.” Despite the perpetual chip on his shoulder and his Dumbo address, our resident Brooklyn Boy is charming, curious, and a talented writer. For Dan, we’re recommending Summer Fun by Jeanne Thornton. 

Summer Fun is an epic, singular look at fandom, creativity, longing, and trans identity. Gala, a young trans woman, works at a hostel in Truth or Consequences, New Mexico. She is obsessed with the Get Happies, the quintessential 1960s Californian band, helmed by its resident genius, B----. Gala writes letters to B---- that shed light not only on the Get Happies, but paint an extraordinary portrait of Gala. The parallel narratives of B---- and Gala form a dialogue about creation--of music, identity, self, culture, and counterculture.

For Nate Archibald, A Little Life by Hanya Yanagihara

Nate Archibald is all blonde hair, blue eyes, and a frown. Our resident sad boy, he’s always brooding over something, whether it’s his father’s catastrophic money mistakes, his extended family’s desire to control him, or the fact that he always picks the wrong girls. For Nate we’re recommending A Little Life by Hanya Yanagihara.

In A Little Life, four classmates from a small Massachusetts college move to New York to make their way. They're broke, adrift, and buoyed only by their friendship and ambition. Over the decades, their relationships deepen and darken, tinged by addiction, success, and pride. It is a tragic and transcendent hymn to brotherly love, a masterful depiction of heartbreak, and a dark examination of the tyranny of memory and the limits of human endurance.

For Chuck Bass, Man Alive by Thomas Page McBee

To many, Chuck Bass is an unredeemable character. The violence that he initially inflicts on others and is inflicted on him is often difficult to watch, but he sees some of the most dramatic character development in the whole series. A difficult man from a difficult home, for Chuck we’re recommending Man Alive by Thomas Page McBee.

In Man Alive, Thomas Page McBee attempts to answer the question “What does it really mean to be a man?” Focusing on two of the men who most impacted his life—one, his otherwise ordinary father who abused him as a child, and the other, a mugger who almost killed him. Standing at the brink of the life-changing decision to transition from female to male, McBee engages an extraordinary personal story to tell a universal one: how we all struggle to create ourselves, and how this struggle often requires risks.

For Jenny Humphrey, Redefining Realness by Janet Mock

Jenny Humphrey is often caught between her big dreams and her youth. Deeply ambitious, she is always fighting trying to figure out what she wants to do with her life. Convinced that if she doesn't have her big break before she turns 16 she will fade into obscurity, for Jenny we’re recommending Redefining Realness by Janet Mock. 

In Redefining Realness, journalist and activist Janet Mock outlines bold perspectives on the realities of being young, multiracial, economically challenged, and trans, recounting her disadvantaged youth and decision to undergo gender reassignment surgery at the age of 18 before pursuing a career and falling in love. Though undoubtedly an account of one woman's quest for self at all costs, Redefining Realness is a powerful vision of possibility and self-realization.

For Vanessa Abrams, Luster by Raven Leilani

Vanessa is the outsider of the show. Despite her position on the fringes of the social scene, she often finds herself unwittingly caught up in other characters’ messes. She is always accidentally ruining plans or rouses because she doesn't know how to play the game. For Vanessa we’re recommending Luster by Raven Leilani. 

In Luster, Edie is stumbling her way through her twenties. She meets Eric, a digital archivist with a family in New Jersey, including an autopsist wife who has agreed to an open marriage—with rules. As if navigating the constantly shifting landscapes of contemporary sexual manners and racial politics weren’t hard enough, Edie finds herself unemployed and invited into Eric’s home—though not by Eric. It is a portrait of a young woman trying to make sense of her life.

 

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Images via The CW Network.

Book descriptions adapted from publisher summaries provided via NYPL’s catalog.