Symbols I Hope This Finds You Well Natalie Sue

The Symbol of Donuts in I Hope This Finds You Well

Introduction: A Sweet Gesture in a Sour Workplace

In Natalie Sue’s I Hope This Finds You Well, donuts appear at several key moments, always brought by Cliff Redmond. They are more than snacks—they become recurring tokens of unexpected kindness within the toxic culture of Supershops Inc. Cliff offers donuts not as bribes or grand gestures, but as small, almost awkward acts of care. Over the course of the novel, the meaning of these donuts shifts: what begins as a puzzling, even suspicious offering transforms into a symbol of genuine connection, vulnerability, and the fragile hope that even in a hostile environment, goodness can exist.

Where Donuts Appear: A Timeline of Offerings

Cliff brings donuts on at least four distinct occasions, each revealing something new about his character and his relationship with Jolene Smith.

  1. Chapter 6 – First meeting in Cliff’s office
    After Jolene confronts Cliff about the surveillance software, she notices a donut box on his windowsill. Cliff later thanks her for coming and says, “Thought you could use one” (paraphrased). This first offer is tentative—he leaves the box in his office, and Jolene does not accept it face-to-face. She dismisses it as meaningless, still distrustful of HR.

  2. Chapter 12 – “Dos and Donuts”
    Cliff brings a box of mini donuts to the whole office. The reception is cold; his colleagues barely acknowledge the gesture. Cliff singles out Jolene, asks her to meet after work, and later sends a direct message apologizing for assuming too much. The note he leaves on the box reads “Not Poison ;)”—a small joke that underscores his awareness of the office’s suspicion. Jolene saves the note, tucking it into her locked drawer.

  3. Chapter 23 – Communication training session
    During one of their mandatory meetings, Cliff arrives with donuts and a PowerPoint. Here the donuts are part of his attempt to create a safe, informal atmosphere. Jolene notices a legal pad with a note about helping her feel safe. The donuts now accompany actual progress in their relationship; Jolene begins to lower her guard.

  4. Chapter 50 – “No Outside Food Allowed”
    A year after the main events, Jolene and Cliff meet at an ice-cream shop. Jolene brings a yellow box of donuts with rainbow icing and sprinkles. She says, “I think I owe you at least…” but is interrupted by the “no outside food” rule. This moment completes the circle: the recipient becomes the giver, and the donuts represent joy and apology instead of suspicion.

How Meaning Changes: From Distrust to Treasured Connection

The donut symbol evolves in parallel with Jolene’s emotional arc. Initially, she views Cliff’s kindness with skepticism—he is “the fucking HR guy” and she fears his motives. In Chapter 12, when he singles her out, she feels exposed and annoyed. Yet she still secretly keeps the note, an early sign that she is beginning to value his sincerity.

Later, the donuts become associated with safety. In Chapter 23, they accompany a session where Cliff gently guides her toward discussing her anxiety. The gesture is no longer awkward but welcome. By the time she returns home in Chapter 50, she discovers an envelope of keepsakes that includes the original Post-it note from the donut box. The revelation “He knew” when he left—he understood her feelings even before she admitted them.

In the final meeting, when Jolene brings donuts to Cliff, the meaning has transformed completely. The donuts are now a deliberate act of reconnection, an acknowledgment of everything he gave her. The fact that the shop’s teen employee scolds them for outside food adds a touch of comic humanity—even a perfect moment can be imperfect. The donuts are no longer about the office; they are about two people caring for each other.

Character Connections: Cliff and Jolene

Cliff Redmond is defined by his consistent, quiet generosity. He brings donuts not because he expects gratitude, but because he genuinely wants to lighten the mood. His note “Not Poison ;)” acknowledges the irony of offering food in a place where trust is poisoned. Cliff’s own backstory—a difficult childhood in a run-down neighborhood—explains why he values small comforts. He tells Jolene that “birds need a nest,” and his office full of trinkets mirrors the same nesting instinct.

For Jolene, accepting the donuts—and later returning them—marks her growth. In the early chapters, she cannot receive kindness without suspicion. By the end, she can offer it freely. Her apology to Cliff during their last training session includes the line: “for the donuts and for showing me there’s good in the world” (paraphrased). This line crystallizes the symbol: the donuts are physical proof of goodness.

Theme Connections

  • Workplace Toxicity and Surveillance
    Donuts arrive in the most surveilled, gossip-filled office imaginable. Cliff’s gesture is immediately weaponized—coworkers speculate about his motives, and Caitlin quips “He could’ve sprung for full-sized ones.” The donuts highlight how even kindness is suspect in a poisoned environment.

  • Empathy Across Differences
    Cliff, an HR representative tasked with punishing Jolene, chooses to show empathy. The donuts are a tangible expression of that choice. They prove that professional roles do not have to prevent human connection.

  • Guilt and Trauma Recovery
    Jolene’s guilt over her sister Ellie’s death makes her feel unworthy of kindness. She initially cannot accept the donuts as genuine. Her gradual ability to keep the note, then to reciprocate, mirrors her healing.

  • Deception and Its Consequences
    Jolene repeatedly lies to Cliff. The donuts contrast with her dishonesty: they are straightforward, uncalculating. When she finally tells the truth, she pairs it with the memory of donuts, linking honesty with the symbol of care.

Study Questions with Answers

1. Why does Cliff leave the note “Not Poison ;)” on the donut box in Chapter 12?
The note is a small joke that acknowledges the office’s lack of trust. Cliff knows his colleagues view him with suspicion—he is new, from HR, and they fear surveillance. By joking about poison, he attempts to disarm that suspicion and show he is harmless. It also reveals his own awareness of the toxic culture: he knows a free treat might be seen as a trick.

2. How does Jolene’s reaction to the donuts change from Chapter 6 to Chapter 50?
In Chapter 6, she barely acknowledges Cliff’s offer and leaves his office without taking a donut. In Chapter 12, she saves the Post-it note but still feels annoyed by the attention. By Chapter 23, she accepts the donuts during their session without protest. In Chapter 50, she brings donuts to him—a complete reversal that demonstrates her growth from guarded resentment to active care.

3. What do the donuts reveal about Cliff’s character compared to other Supershops employees?
Cliff uses donuts as a genuine attempt to connect, while coworkers like Caitlin and Rhonda mock the gesture or pick the box clean without gratitude. His willingness to be vulnerable—bringing treats despite the cringe-inducing reception—shows he prioritizes human connection over corporate image. Unlike Gregory or Anna, he does not use the donuts as a power play.

4. How does the “no outside food” rule in Chapter 50 affect the symbolic weight of the donuts?
The rule creates a comic obstacle that prevents the gesture from being sentimental. Jolene’s attempted apology is interrupted, and both characters laugh. This imperfection makes the symbol more human: the donuts are not a tidy resolution but a messy, real attempt at reconnection. It reinforces that kindness does not need to be flawless to be meaningful.