The To-Do List: From Flirtation Checklist to Guide for Reclaiming a Life
Introduction
In How to Fail at Flirting, Denise Williams weaves a deceptively simple motif—the to-do list—into a layered symbol of Naya Turner’s journey from survival to authentic living. What begins as a playful, friends-imposed list of sexual and social goals transforms into a deeply personal tool for regaining control, setting boundaries, and eventually building a life she actually wants. The list recurs at key moments, each time reflecting Naya’s shifting relationship with vulnerability, trust, and self-advocacy.
What the To-Do List Literally Is
The to-do list first appears in Chapter 2 as a physical piece of paper on which Aaron writes “Nay’s To-Do:” and then item number one: Sex with a stranger. Felicia prompts him to add items like “Flirt” and “Let a guy buy you a drink.” Naya, initially resistant, mentally appends her own deeper desires: Stand up for myself, Take risks, Let someone else get me to orgasm, Trust a man again. This hybrid list—part joke, part earnest wish—becomes a silent guide.
Later, the list appears not as shared paper but as private mental notes or written reminders. In Chapter 5, Naya adds To do: Figure out what to wear to this thing as she prepares for a work event. In Chapter 23, she writes To do: Find more writing projects to keep my mind busy and then, more darkly, To do: Figure out how to make money stripping when I lose my job. By Chapter 43, the list has become a lifeline: To do: Make an appointment with a counselor.
The motif also appears in a parallel form when Jake sends Naya his own list of things he likes about her in Chapter 25. This list, which catalogues her laugh, her cheese puns, and the sound she makes when he kisses her neck, offers a mirror to the original—replacing obligation with delight.
Where the Motif Recurs
| Chapter | What Happens | Significance |
|---|---|---|
| 2 | Aaron and Felicia create the paper list; Naya adds mental items | The list is born from friends’ love and Naya’s hidden need for agency |
| 5 | Naya writes a mental to-do about clothing for the Barth House event | Shows the list expanding into daily life, still tied to performance |
| 23 | Naya creates a series of anxious to-dos about her career and finances | Reflects her fear of job loss and her habit of using lists to manage anxiety |
| 25 | Jake sends a playful list of Naya’s qualities | Contrasts the original list: it celebrates her without demanding change |
| 34 | Naya mentally notes that she has to deal with Davis again | The list becomes a survival tactic, a way to brace against old trauma |
| 43 | Naya writes “Make an appointment with a counselor” | The list now serves self-care, not self-criticism or performance |
| Epilogue | Naya has bought a house with Jake, earned tenure, healed with Jill | The list is no longer needed as a crutch; her life has become the fulfilled version of those early wishes |
Each recurrence deepens the list’s symbolic load. It is never static: it shifts from external pressure to internal compass.
How Its Meaning Changes
From Performance to Authenticity
The original list, imposed by Aaron and Felicia, is about doing things for others—being fun, flirting, having sex. Naya’s initial mental additions (Stand up for myself, Trust a man again) already tug the list toward her own needs, but the public version stays in the realm of performance. Over time, Naya stops trying to check off items for her friends’ approval and starts using her private to-dos to navigate real crises.
From Fear to Self-Advocacy
In Chapter 34, when Davis reappears on campus, Naya’s internal list becomes a shield: “I just have to deal with him. I did it before. I can do it again.” This defensive use of the list shows her falling back on old survival patterns—endurance rather than healing. But by Chapter 43, the list item Make an appointment with a counselor signals a shift from enduring alone to seeking support.
From Checklist to Permission Slip
The list’s final transformation is into a permission slip for joy. Naya’s early reluctance to even keep the list gives way to using it as a guide for taking risks—going to the bar with Jake, admitting she wants more than a one-night stand, and eventually trusting him enough to build a shared future. The list stops being about tasks and becomes about honoring her own desires.
Character and Theme Connections
Naya Turner – The list mirrors her arc from a woman who hides behind shapeless clothes and rigid routines to one who allows herself pleasure, anger, and vulnerability. Each time she adds a mental to-do, she is quietly reclaiming a piece of her life that Davis had taken.
Jake Shaw – His own list—a sweet, catalogued description of Naya’s physical and personal qualities—stands as an antithesis to the original. Where Aaron and Felicia’s list treated Naya as a project, Jake’s list treats her as a person already complete. This contrast helps Naya learn that she does not have to perform or change to be worthy of love.
Felicia and Aaron – Their love is genuine, but their list reveals their limited understanding of Naya’s trauma. They see a friend in a rut; they do not see the wounds. Over time, Naya’s private list becomes the true record of her needs, precisely because her friends cannot write it for her.
Themes of trauma recovery – The list’s evolution tracks Naya’s recovery from intimate partner violence. Early items focus on external actions (sex, drinking), but later items address internal healing (trust, counseling). This mirrors the real path from survival to thriving.
Themes of trust and vulnerability – Naya’s willingness to share her real list—or even to admit she has one—grows as she learns to trust Jake and her friends with her past. The list becomes a test of vulnerability: she hides it, then uses it, then outgrows it.
Self-advocacy and communication – The list functions as a private rehearsal for public advocacy. When Naya finally tells Jake the truth about Davis, when she reports Davis’s threats, and when she sets boundaries with her department, she is checking off items that began as silent vows.
Study Questions
1. How does the to-do list embody Naya’s struggle between external expectations and internal needs?
Answer: The list begins as a joke imposed by friends who want Naya to “have fun,” but Naya immediately rewrites it mentally to include Stand up for myself and Trust a man again. This split between the paper list (public, performative) and the mental list (private, authentic) illustrates her lifelong habit of hiding her true struggles. Her recovery involves integrating the two lists: learning that fun and healing are not opposites.
2. Why does Jake’s personal list of Naya’s qualities matter to the story’s theme of reclaiming agency?
Answer: Jake’s list is never a to-do; it is a celebration of who Naya already is. He lists her laugh, her cheese puns, the way she grips his hair. This shifts the symbolic meaning of “list” from something that demands change to something that affirms worth. It gives Naya permission to stop treating herself as a fixer-upper and start believing she is enough.
3. How does the list’s tone change when Davis blackmails Naya in Chapter 23?
Answer: In the aftermath of Davis sending her a nude photo and threatening her career, Naya does not write a new list. Instead, she clutches her phone like a teddy bear and mentally tells herself, “I’ll deal with it. I always deal with it.” The absence of a formal list here is telling: Davis’s control robs her of the structured thinking that lists represent. Only when she begins to reclaim her voice does the list return, now as a tool for self-rescue.
4. What does the final to-do in Chapter 43—“Make an appointment with a counselor”—reveal about Naya’s character development?
Answer: This item marks the first time Naya explicitly includes professional mental health care on her list. Earlier to-dos were about external actions (sex, clothing, work). Here, she acknowledges that healing from abuse requires structured support. The shift from “I can handle it alone” to “I need help” reflects the deepest learning of her journey: that reclaiming her life means trusting others with her vulnerability.
Conclusion
The to-do list in How to Fail at Flirting is far more than a plot device or a running joke. It is a dynamic symbol of Naya’s struggle for control, her fear of being seen, and her eventual embrace of authentic living. Starting as a flirtation checklist written by friends, it evolves into a private document of self-rescue, a permission slip for joy, and finally a set of fulfilled hopes no longer requiring paper. For readers tracing themes of trust and vulnerability, power dynamics in academia, and consent and communication, the list offers a compact lens through which to watch one woman reclaim her story.