Chapter 6. Kill the Creator of ‘Entourage’ in Your Head

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Gutowitz traces how the “boys’ club” culture of the 2000s—epitomized by the HBO series Entourage—conditioned her to seek male validation and see other women as competition. She recounts a pivotal moment in college when a male peer, Noah, hired her for a satire blog and complimented her as “the only funny girl,” which reinforced the idea that women must be exceptional to be accepted. After moving to Los Angeles, she discovers Orange Is the New Black, a show centered on queer women that helps her realize her own lesbian identity. The series becomes a cultural turning point, making lesbianism visible and “cool” on a mainstream scale. Later, she recognizes she had simply transferred her need for approval from straight men to gay men, still measuring her worth against male standards. The chapter concludes with Gutowitz rejecting the need to relive painful memories (the “Nostalgia” drug from Watchmen) and committing to a self-defined, queer vision of cool.

Key Events

Gutowitz describes watching Entourage in high school with male friends, feeling sickened by the show’s misogyny but participating to gain acceptance.
In college, she meets Noah, head writer of the Ramapo Underground satire blog. He hires her, then at a party calls her “the only funny girl I’ve ever met” and kisses her; they date briefly before he ghosts her.
After college, Gutowitz moves to Los Angeles. On the day Orange Is the New Black premieres (July 11, 2013), she watches the pilot in a Starbucks, panicking when nudity appears, and later binge-watches all thirteen episodes alone on her iPhone.
Season two of the show (2014) prompts her to host a watch party with queer friends, solidifying her sexual awakening.
Gutowitz reflects on receiving praise from a gay male friend who says she offers “Gay Twitter” content from a lesbian perspective, which initially flatters her but later feels like a repeat of the “one of the boys” dynamic.
She lists iconic lesbian celebrities (Kristen Stewart, Jodie Foster, etc.) as models of coolness that reject male-approved standards.

Character Development

Jill Gutowitz – Moves from seeking approval from men (first straight, then gay) to embracing her lesbian identity and defining coolness on her own terms. She unlearns the internalized belief that women—especially lesbians—are somehow less worthy.
Noah – Represents the gatekeeping “nice guy” who doles out conditional validation; his compliment is both a prize and a trap.
Doug Ellin (creator of Entourage) – Symbol of the toxic media that shaped Gutowitz’s worldview.
Jenji Kohan – Creator of Weeds and Orange Is the New Black; her work provides an alternative, female-driven narrative.
Alex Vause and Piper Chapman – Fictional characters whose relationship catalyzes Gutowitz’s self-recognition as a lesbian.

Themes, Symbols, or Motifs

The “Boys’ Club” vs. Queer Community – The chapter contrasts male-dominated spaces (frat parties, Entourage viewing parties) with the affirming, women-centered world of Orange Is the New Black.
Nostalgia (Watchmen drug) – A symbol for the compulsive revisiting of painful memories, which Gutowitz uses to examine how pop culture shaped her.
Visibility and Representation – “You have to be able to see yourself to see yourself.” Seeing queer women on-screen is essential for self-discovery.
“One of the Boys” as a Trap – The false promise that women can gain power by aligning with men; Gutowitz later recognizes this pattern in seeking approval from gay men.

Why This Chapter Matters

This chapter is the emotional and intellectual core of Girls Can Kiss Now. Gutowitz demonstrates how media consumption directly influences identity formation, particularly for queer women who grow up without representation. It also critiques the idea that women must “earn” a place in male-dominated fields (like comedy) by being exceptional. By connecting her personal story to larger cultural shifts—the rise of streaming, the explosion of queer TV after Orange Is the New Black—she shows how structural change can happen alongside personal transformation. The chapter’s title, “Kill the Creator of ‘Entourage’ in Your Head,” becomes a call to reject internalized misogyny and homophobia.

Study Questions and Answers

How does Gutowitz use the concept of “Nostalgia” from Watchmen to structure her essay?
The fictional drug Nostalgia allows users to relive memories, often traumatic ones. Gutowitz compares her own obsessive re-watching of Entourage to this experience—she revisits the show not for pleasure but to understand how it scarred her. She eventually decides to “pour the Nostalgia pills down the drain,” i.e., cancel her HBO Max subscription, symbolizing a refusal to keep re-litigating her past through toxic media.
What does the interaction with Noah reveal about the “only funny girl” trope?
Noah’s compliment makes Gutowitz feel special, but she later realizes it reinforces the harmful idea that women are rarely funny and that a lone woman must be an exception to be accepted. This dynamic pits women against each other and keeps the “boys’ club” intact. The relationship ends when he ghosts her, showing that male validation is never truly granting membership—it still leaves women disposable.
Why does Gutowitz initially feel she doesn’t fit in with the lesbian community, and how does she resolve that?
After coming out, she couldn’t relate to classic lesbian stereotypes (Subarus, U-Hauling). Her interests aligned more with gay male pop-culture fandom. She realizes she was still seeking approval from a male-dominated group (gay men) rather than embracing her own community. By naming that “heteronormative brain rot,” she begins to find value in being “that kind of lesbian” and redefines lesbian canon on her own terms.