Gretchen in Imogen, Obviously: The Gatekeeping Best Friend

Overview

Gretchen is Imogen Scott’s confident, outspoken queer best friend from high school. She dyes her hair, fills rooms with her presence, and positions herself as an authority on queer issues. Throughout Imogen, Obviously, Gretchen acts as both an educator and an obstacle to Imogen’s self-discovery. While she genuinely wants to protect queer spaces and people, her rigid definitions of queerness ultimately lead her to invalidate Imogen’s questioning. By the end of the novel, Gretchen’s relationship with Imogen fractures, making her a crucial catalyst for Imogen’s independent identity.

Plot Role and Chronological Arc

Gretchen is established early as a fixture in Imogen’s life. In a flashback to ninth grade, Gretchen educates Imogen about straight women joking about same-gender attraction (ch. 9). Later, a memory shows Gretchen being aggressively misidentified as hitting on a homophobic girl in a bathroom, underscoring the real harm of stereotypes (ch. 9). The arc progresses through several key moments:

• Ch. 7 – A flashback reveals that Gretchen once called out Imogen for feeling uncomfortable when Gretchen talked about liking girls. Imogen internalizes this as a bias she must correct.
• Ch. 9 – Gretchen schools Imogen on why “I’d kiss Clea DuVall” is problematic, conflating a genuine feeling with straight appropriation.
• Ch. 31 – Gretchen repeatedly calls Imogen a “freaking heterosexual,” dismissing any possibility that Imogen might be questioning.
• Ch. 39 – When Imogen admits Tessa is cute, Gretchen asks “Do you want to fuck her?” and takes Imogen’s hesitation as proof she is straight—invalidating her crush.
• Ch. 50-51 – The pivotal diner confrontation: Gretchen accuses Imogen of appropriating queerness after Imogen confesses the fake relationship. Edith defends Imogen; Gretchen refuses to accept Imogen’s identity.
• Ch. 57 – Gretchen sends a non-apology text (“You were hurt”), which Lili calls out as insufficient.
• Ch. 61 – Imogen reflects that Gretchen was the first person she came out to, but her dismissal may mean the friendship is over. Gretchen becomes “backstory.”

Motivations and Traits Shown Through Actions

Gretchen’s actions reveal deep-seated motivations:

• Protection of queer spaces – She draws on her own trauma: a middle school GSA disbanded by cishet boys mocking labels (ch. 32). This explains her gatekeeping at Pride meetings, where she scrutinizes newcomers who decline labels.
• Desire to be seen as authoritative – She frequently lectures Imogen on compulsory heterosexuality, gender performance, and appropriation. She posts educational graphics online (ch. 32).
• Need for control – When Imogen mentions Tessa, Gretchen immediately interrogates the crush with a “sex test” (ch. 39). She cannot tolerate ambiguity in Imogen’s identity.
• Genuine care mixed with invalidation – Her gifts (pink velvet bow, Vassar teddy bear) are peace offerings, but as Edith notes, Gretchen “stirs shit up and then makes up for it with gifts” (ch. 40). This pattern allows her to avoid deep accountability.

Relationships

Imogen

Gretchen’s relationship with Imogen is asymmetrical. Imogen admires Gretchen’s confidence and often lets Gretchen define her. Imogen describes feeling “like I’m stealing” when she thinks of herself as bi (ch. 50). Gretchen’s repeated dismissal makes Imogen question her own feelings for Tessa. The friendship ends not with a dramatic fight but with Imogen recognizing that Gretchen cannot offer validation, and that may be acceptable.

Edith

Edith sees through Gretchen’s dynamics clearly. She points out that Gretchen creates drama and then smooths it over with gifts (ch. 40). During the Kara Clapstone argument (ch. 34), Edith defends bisexuals against Gretchen’s criticism. Edith ultimately stands up for Imogen at the diner, calling out Gretchen directly.

Lili

Lili and Gretchen have a long-standing tension. At a Seneca Farms ice cream shop (ch. 32), Lili challenges Gretchen’s assumption that a Pride attendee who declined labels is cishet. Lili argues against gatekeeping, while Gretchen defends it from her painful middle-school experience. Later (ch. 57), Lili criticizes Gretchen’s non-apology text, showing she understands the damage.

Key Decisions and Consequences

Gretchen’s refusal to leave space for Imogen’s questioning directly contributes to Imogen’s initial shame and her eventual need to claim her identity without Gretchen’s approval.

Theme and Symbol Connections

• [Self-discovery and queer identity] – Gretchen embodies the fear Imogen has about not being “queer enough.” Her gatekeeping becomes an obstacle to Imogen’s self-acceptance.
• [Compulsory heterosexuality] – Gretchen’s tests (the “sex test”) reinforce the idea that attraction must be physical or quantifiable, ignoring the nuanced experience of compulsory heterosexuality.
• [Authenticity vs. performance] – Gretchen accuses Imogen of appropriating queerness, failing to see that Imogen’s performance (the fake relationship) is a mask for real confusion. The novel argues that performance can be a pathway to authenticity.
• [Queer community and allyship] – Gretchen’s protectiveness stems from a valid fear of invasion, but the novel questions whether gatekeeping helps or harms community. Her trauma from middle school does not justify invalidating a questioning teen.
• [Friendship and belonging] – Gretchen’s friendship with Imogen is conditional on Imogen staying within a predetermined identity. The novel suggests genuine belonging requires mutual respect for each person’s unique journey.

The pink teddy bear (ch. 30) and the velvet bow (ch. 38) are symbols of Gretchen’s love language—material gestures that mask lack of emotional validation. They represent her pattern of smoothing over conflict without confronting its root.

5 Book-Specific Questions and Answers

1. Why does Gretchen react so strongly when Imogen says she might have a crush on Tessa?
Gretchen has a history of straight women joking about same-gender attraction, which she experienced as erasure. When Imogen hesitates, Gretchen interprets it as proof that Imogen is straight, because any real attraction would be immediate and clear. This reaction reflects Gretchen’s trauma and her rigid definition of queerness—she cannot imagine a questioning person who doesn’t already have an answer.

2. What role does Gretchen’s middle school GSA experience play in her behavior?
In chapter 32, Gretchen describes how cishet boys from the basketball team used labels to mock her GSA until the group disbanded. This trauma makes her hypervigilant about potential “invaders” in queer spaces. She projects this fear onto Imogen, misreading Imogen’s uncertainty as cishet performativity.

3. How does Gretchen’s confrontation at the diner affect Imogen’s arc?
Gretchen’s accusation that Imogen is appropriating queerness forces Imogen to confront her internalized doubt. It also clarifies that Imogen cannot rely on Gretchen for validation. Afterward, Imogen realizes she must define her own queerness, starting with her confession to Tessa and her embrace of the term “bisexual” without apology.

4. What does Edith’s criticism of Gretchen reveal about their dynamic?
Edith tells Imogen that Gretchen “stirs shit up and then makes up for it with gifts” (ch. 40). This pattern shows that Gretchen uses material gestures to avoid emotional accountability. Edith sees that Imogen habitually lets Gretchen remold her, and she encourages Imogen to break free.

5. Does Gretchen have a valid point about protecting queer spaces, or is she just gatekeeping?
The novel portrays Gretchen’s concerns as understandable—she has real trauma from middle school. However, the narrative suggests that gatekeeping based on identity tests harms questioning individuals. Other queer characters, like Lili and Tessa, model a more inclusive approach: they accept Imogen’s self-identification as it evolves. The book argues that protection of spaces should include room for exploration, not just rigid definitions.

Conclusion

Gretchen is a complex, well-meaning character whose pain leads her to enforce boundaries that exclude the very people she wants to protect. Her relationship with Imogen illustrates how even close friends can inadvertently obstruct another’s self-discovery. By the end, Imogen chooses growth over Gretchen’s approval, and Gretchen’s role shifts from gatekeeper to backstory—a necessary loss on the path to authentic identity. Readers interested in more about Imogen’s journey can read the [ending explained] or explore [questions and answers] about the novel.