The Courage to Take Risks for Love and Self-Determination in Pride and Prejudice and Pittsburgh

The Thematic Claim: Risk as the Price of Self-Determination and Love

In Pride and Prejudice and Pittsburgh, Rachael Lippincott builds a story around a deceptively simple idea: happiness and self-fulfillment are never guaranteed, and they are only reachable when characters dare to defy expectations and take bold risks, even when the outcome is uncertain. This theme drives the novel’s central conflicts—Audrey’s artistic paralysis and fear of love, Lucy’s suffocating duty to her father, and the impossible choice to be together across two centuries. The narrative repeatedly shows that playing it safe—whether by hiding from art, submitting to an arranged marriage, or refusing to acknowledge one’s feelings—leads to a life of quiet resignation. Only by risking rejection, scandal, and even the fabric of time itself do the characters earn the chance at genuine love and self-determination.

Audrey’s Paralysis: The Cost of Avoiding Risk

The novel opens with Audrey Cameron, a young artist who has stopped drawing since her breakup with Charlie. She is wait-listed at RISD and must submit five new pieces, but her sketchbook remains blank. Her fear is not just about rejection from art school; it is a deeper fear of putting herself out there again. As she tells her mother, she feels that “wait lists and rejections and heartbreaks are all that’s ever waited for me on the other side” (Chapter 3). This mindset is a direct result of her past risk—loving Charlie and pursuing art—which ended in pain. So she decides to let RISD go, to stop drawing, and to hide in the safety of her family’s convenience store.

The character of Mr. Montgomery serves as the catalyst for challenging this avoidance. He tells Audrey, “There’s just as much heartbreak in not putting yourself out there, because it guarantees you’re going to miss out” (Chapter 5). This line becomes the novel’s thematic thesis. Mr. Montgomery’s gift of a quarter—a symbol of chance and risk—sends Audrey hurtling into 1812, forcing her to confront the very fears she has been avoiding. The quarter is not just a plot device; it represents the unpredictable leap of faith that Audrey must take, both literally and metaphorically.

Lucy’s Trapped Duty: The Fear of Defying Expectations

In contrast to Audrey’s modern freedom, Lucy Sinclair lives in 1812, where her father dictates her future. She is expected to marry Mr. Caldwell, the county’s richest man, to improve her father’s business prospects. Lucy dreads this, viewing Caldwell as a fool twice her age, but she has spent two months subtly resisting his advances without success. Her fear is not just of her father’s anger but of the entire social system that leaves her no other option. As she tells Audrey, “It’s just… how things are, Audrey. What we as women are expected to do. Marry well, try not to be a burden, bear sons who won’t have to suffer the same reality” (Chapter 14).

Lucy’s internal conflict is rooted in the risk of defying her father. She is afraid of him, as Audrey observes: “She’s afraid of him. And, worst of all, she can’t escape him. Unless she marries, she’d have no place to go, no home, if she doesn’t do exactly as he says” (Chapter 27). This fear keeps her trapped in a neat little box of propriety. Yet, through her conversations with Audrey, she begins to question whether the risk of love might be worth it. When Audrey asks if she would be brave enough to choose for herself, Lucy wonders, “Would it be worth the risk? Would I be brave enough if I can’t even risk my father’s ire over some books?” (Chapter 14). This moment reveals that Lucy’s paralysis is not just about marriage—it is about her entire sense of agency.

The mother’s portrait becomes a symbol of the love and choice that Lucy’s mother believed in. Lucy gazes at it, reflecting on her mother’s belief that she would marry for love—a belief that now seems foolish. The portrait represents the ideal of self-determination that Lucy has been taught to abandon. It is a reminder that risk, even if it leads to heartbreak, is preferable to a life without choice.

The Turning Point: Choosing to Risk Everything

The climax of the novel occurs on Lucy’s wedding day, when she must decide whether to go through with the marriage or to object. This is the ultimate risk: defying her father, Mr. Caldwell, and the entire social order. Lucy’s declaration, “I am choosing myself” (Chapter 38), is a powerful act of self-determination. She risks everything—her home, her reputation, her future—to assert her own will. The scene is chaotic: Martha shoves smelling salts under Mr. Caldwell’s nose, and Lucy flees with Alexander and Mr. Shepherd. But the risk is not just Lucy’s. Audrey, who has been tied up in the library by Lucy’s father, also takes a risk by returning to save Lucy. She had earlier learned from Mr. Montgomery that there is a loophole: if both she and Lucy want to be together, they can return to the present. But this requires Audrey to be brave enough to ask, and Lucy to be brave enough to choose herself.

Audrey’s realization in Chapter 37 is crucial: “If I’m brave enough. And now I am. After these past few weeks, after this truly unbelievable journey, I am brave enough to ask her for that. To take the risk and hope that she chooses me. But, more importantly, that she chooses herself, too.” This moment shows that Audrey has internalized the lesson Mr. Montgomery taught her. She no longer sees risk as something to avoid but as the only path to a meaningful life.

The Resolution: Risk Rewarded with Self-Determination

The novel’s resolution affirms that the risk was worth it. Lucy and Audrey return to 2023 together, and Lucy begins to build a new life—studying for her GED, working at the corner shop, and performing at a local bar. Audrey receives a RISD acceptance letter but chooses to take a gap year so they can explore the modern world together. This decision is itself a risk: Audrey is giving up a guaranteed spot at her dream school to prioritize her relationship with Lucy. But it is a choice made freely, not out of fear. The epilogue shows them at prom, with Lucy admitting she doesn’t know the steps, and Audrey responding, “We’ll figure it out together” (Chapter 40). This line encapsulates the theme: love and self-determination are not about having all the answers but about taking the leap and trusting that you can navigate the unknown together.

The sketchbook also completes its arc. It begins as a symbol of Audrey’s creative block, but by the end, it is filled with drawings of Lucy and her journey. The sketchbook represents the risk of artistic expression—putting pencil to paper without knowing if the result will be perfect. Audrey learns that her art was never dependent on a crush or heartbreak but on her own belief in herself. As she reflects in Chapter 37, “I took risks on and off the page, knowing that pain could and would probably follow, but… I enjoyed the good and I faced the consequences, too.”

Complexity and Contradiction: The Double-Edged Nature of Risk

The novel does not present risk as a simple solution. It acknowledges that risk can lead to pain, as Audrey experienced with Charlie, and as Lucy fears with her father. The theme is complicated by the fact that not all risks are equal. Lucy’s risk of defying her father is not just emotional but physical—she could be cast out with no home. Audrey’s risk of loving Lucy across time is not just social but existential, as she risks losing her entire world. Yet the novel argues that the alternative—playing it safe—is a guaranteed loss. As Mr. Montgomery says, “You won’t find any of it if you hide from it here” (Chapter 5).

There is also a contradiction in Audrey’s character. She begins the novel believing that love is a “total scam” and that she should never put herself out there again. But her journey forces her to confront this belief. She realizes that her fear of heartbreak was actually a fear of living fully. The novel suggests that risk is not about being reckless but about being brave enough to face uncertainty. Lucy’s objection at the wedding is not impulsive; it is a calculated act of self-preservation. Audrey’s decision to return to 1812 is not a whim; it is a deliberate choice to fight for love.

The quarter symbolizes this duality. It is a coin—a small, everyday object—but it carries the power to change everything. It represents the unpredictable nature of risk: you never know where it will land. But the novel shows that the act of tossing the coin—of taking the chance—is what matters.

Study Questions and Answers

1. How does Audrey’s initial decision to give up on RISD reflect her fear of risk?

Audrey’s decision to abandon her RISD application is a direct result of her fear of rejection. After Charlie broke up with her, she stopped drawing, and she interprets her blank sketchbook as a sign that she should let go of her dream. She tells her mother that she feels like “a sign” to let RISD go. This avoidance is a way to protect herself from potential failure, but it also guarantees she will never succeed. Mr. Montgomery’s intervention forces her to see that not taking a risk is itself a loss.

2. What role does Mr. Montgomery play in challenging Audrey’s and Lucy’s attitudes toward risk?

Mr. Montgomery serves as the novel’s mentor figure. He gives Audrey the quarter that sends her to 1812, and he later explains that the universe sends people where they are needed. He tells Audrey that true love and inspiration are “out there” and that she won’t find them by hiding. For Lucy, Mr. Montgomery’s existence as a time traveler demonstrates that defying expectations is possible. His backstory—being trapped in a coal mine and wishing his way to the 1300s—shows that risk can lead to extraordinary outcomes.

3. How does Lucy’s objection at the wedding represent an act of self-determination?

Lucy’s objection is the culmination of her internal struggle. She has been told her entire life that her duty is to marry well, but she realizes that this would mean sacrificing her own happiness. By declaring “I am choosing myself,” she rejects her father’s authority and the social norms that have trapped her. This act is risky because she has no guarantee of a future, but it is the only way she can assert her agency. The fact that she flees with Alexander and Mr. Shepherd shows that she is willing to face the consequences.

4. What does the sketchbook symbolize in relation to the theme of risk?

The sketchbook represents Audrey’s creative and emotional vulnerability. At the start, it is blank because she is afraid to draw, just as she is afraid to love. As she takes risks in 1812—forming friendships, confronting her feelings for Lucy, and eventually choosing to return—the sketchbook fills with images that reflect her journey. By the end, it is a testament to her willingness to put herself on the page, even if the result is imperfect. The sketchbook shows that risk is necessary for both art and love.

5. How does the novel address the contradiction that risk can lead to heartbreak?

The novel acknowledges that risk can cause pain—Audrey’s heartbreak with Charlie is a clear example. However, it argues that avoiding risk guarantees missing out on the possibility of joy. Mr. Montgomery’s line, “There’s just as much heartbreak in not putting yourself out there,” encapsulates this idea. The novel also shows that heartbreak can be a learning experience. Audrey’s past heartbreak helps her recognize what she truly wants, and Lucy’s fear of her father ultimately gives her the courage to defy him. The contradiction is resolved by the idea that the risk of love is worth taking, even if it doesn’t always work out, because the alternative is a life without choice.