I Hope This Finds You Well

Cliff Redmond is Jolene’s love interest. As the novel opens, Cliff is a newly hired human resources analyst at Supershops. From the start, Cliff reveals himself to be sensitive and thoughtful, with a fun sense of humor. Cliff’s character is further enhanced by allusions to his favorite pop culture topics, including Bob’s Burgers, Star Wars, and Warhammer 40,000. In terms of motivation, Cliff acts primarily out of a desire to help others; he moves to Calgary in order to help his grandmother, who is recovering from a medical procedure. When Gregory makes misogynistic comments about Caitlin, Jolene notes that “Cliff’s voice cuts sharper than [she’s] ever heard” in retaliation (170). Unsurprisingly, Cliff struggles when his job requires him to deliver bad news to others, as when Larry’s firing goes disastrously awry.

Cliff’s development through the novel involves his gaining the confidence to leave behind a job that he finds unpleasant at best and downright repulsive at other times. In so doing, Cliff thanks Jolene for inspiring him to be brave. Meanwhile, he is persistent in reaching out and supporting Jolene even after he learns that she was reading his emails. As romantic partners, Cliff and Jolene thus complement each other, with Cliff having a softer, more socially conscious outlook, while Jolene is bolder in expressing herself. Overall, Cliff’s character demonstrates the value of supportive, reliable friends.

Rhonda Staples is the lead accounting administrator at Supershops but mostly serves as Gregory’s assistant. As an older adult who is nearing retirement age, Rhonda sometimes struggles to keep up with technological advancements; her last name seems to point to her continued use of physical documentation over digital. This preference leads to friction with her digital-only coworkers, particularly Armin, whose movements Rhonda tracks meticulously as she builds a case for him to be dismissed. Meanwhile, Rhonda presents herself as a proud and happy mother of an adult son, Carl, even as she secretly mourns the fact he has an addiction (although Carl’s experiences with addiction are unspecified). To fill the empty hours, Rhonda sets up an online dating profile but fails to make any real connections.

Rhonda’s arc throughout the novel is one of reconciliation and renewal. At first, she and Jolene hardly interact: A few years earlier, a misunderstanding about Christmas decorations left the two of them at odds. After Jolene decides to ingratiate herself to Rhonda, Rhonda comes to appreciate Jolene’s kindness and capability. Even after learning about Jolene’s deceptive behavior, Rhonda writes her a frank letter expressing her understanding. Rhonda’s connection with Miley, meanwhile, allows her to fill a parental role in a more active way than she could with Carl. Rhonda’s development demonstrates that a person can continue learning, changing, and growing, regardless of age.

Armin Habib is one of Jolene’s coworkers in the accounting department. As the novel opens, Armin is generally bored and undisciplined at work. Early on, Jolene describes him as “a serial printer breaker who walks away when faced with any adversity from IT equipment—or any minor challenge, really” (9). Armin’s tendency to crumble in the face of challenges is also manifest in more significant ways, especially his fabricated engagement with Jolene. Armin invents the engagement to please his parents, especially his dying mother, even as he lies about his role at Supershops, making it seem grander than it is. As the novel progresses, Armin is forced to begin shouldering responsibility for the consequences of his lie, which spiral out of control as his parents begin to plan a massive wedding. Eventually, Armin does come clean to his parents, allowing him to share a moment of authenticity and vulnerability with his mother before she passes away. Armin thus exemplifies a dangerous extreme when it comes to pleasing other people instead of acting independently, at least until he realizes his mistake.

Caitlin Joffrey is Jolene’s coworker in the accounting department, and the two fill parallel roles, making them foil characters. Due to a long-standing, petty feud between the two of them, Caitlin and Jolene act as rivals, particularly as they compete for an upcoming promotion. Like Jolene, Caitlin struggles with insecurities and anxiety, but she deals with them in different ways. Instead of trying to escape negative feelings through various distractions, she tries to build up her self-esteem by maintaining an apparently picture-perfect life on social media, even as she employs positive self-talk. As Jolene discovers, Caitlin’s passwords include “Iamworthy44” “Iambeautiful19” and “Iamagoddess19” (81). What Jolene mistakes for vanity is actually a desperate attempt by Caitlin to maintain her sense of self-worth despite mounting personal and professional pressures.

Caitlin’s arc involves her learning to respect Jolene, just as Jolene comes to respect her. Although Caitlin is responsible for reporting Jolene’s behavior to human resources, which results in her losing her job, by the time the two come face to face at Rhonda’s retirement party, Caitlin acknowledges that Jolene was right about Kyle, her abusive ex-boyfriend. Caitlin’s growth demonstrates the courage that is required to end an abusive relationship.

Jolene’s parents, Leila and Albert, demonstrate two varying extremes of parenting, as well as the downsides associated with them. From Jolene’s perspective, her mother is too nosy and prying when it comes to Jolene’s personal life. Her father, meanwhile, is too distant and detached. Although her parents move to Calgary to be near Jolene, she pushes them away due to her fear of disappointing them, even as she pretends that all is well. As the novel concludes, Jolene’s relationship with her parents is renewed as she reveals the recent disappointments in her life. In so doing, she receives the support she needs from them. Jolene’s mother also agrees to certain boundaries so long as Jolene allows her to be involved in her life, as Jolene’s father agrees to meet her for lunch, showing that he is also willing to become more involved. Jolene’s relationship with her parents demonstrates the need for clear communication and healthy expectations in parent-child relationships.

Jolene’s boss at Supershops, Gregory, is presented as an unsavory, even grotesque character. Early on, Jolene describes Gregory’s presence in starkly sexual terms:

The single most notable thing about him is that he often discreetly touches his penis (via his pockets, but we can all see the movements) and then openly touches the door handles, printers, and Nespresso buttons, leaving his penis dew that seeped through the pocket fabric everywhere. Because he’s the boss, there’s no stopping his dick fingers, and that’s why no workplace is ever truly equal (4).

On another occasion, Jolene reflects on Gregory’s disrespect for her bodily autonomy, noting, “I’ve lost track of how many times I’ve been touched against my will by this man” (13). Although he is humbled in the end, Gregory’s character illustrates the way that gender politics intersect with traditional office hierarchies, which have historically been dominated by men.