Chapter 8 'Leaving' – Summary and Analysis

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Chapter 8, “Leaving,” traces Molly Shannon’s final years in high school and her determined path toward NYU’s Tisch School of the Arts. The chapter opens with a small but telling obstacle: achievement tests that would help with college admissions required a check from a parent, and Molly knew her father would attach strings to any financial help. Rather than ask, she simply didn’t take the tests, a decision that reinforced her independence and her desire to earn her own money.

Her father, Jim Shannon, actively discouraged academic effort. He told her to cheat on tests whenever possible and encouraged her to cut school entirely. When Molly was stressed, he’d propose calling in sick and driving downtown for lunch, or visiting swing sets by the lake and eating chili and crackers at an old-fashioned coffee shop. He admired strong female performers, and when he saw a newspaper photo of Elizabeth Taylor in National Velvet, he insisted it looked like Molly and saved the clipping.

As Molly and her sister Mary entered high school, they began drinking at keg parties. Their father didn’t forbid it, reasoning that open communication was safer than prohibition. He insisted they call him rather than drive after drinking, and they listened. He also bought them Candie’s high heels and discounted mink coats, telling them to look glamorous in church. A librarian mother at school called the shoes “prostitute shoes,” but Molly defended her father’s taste.

The family’s unconventional social life extended to Traxx, a downtown gay bar, where Molly and Mary wore their mink coats and drank beer. Their father, off the wagon, partied with Molly’s friend Alison. One night he got into a silly confrontation with a bouncer, then returned with his car to block the bar’s entrance. Alison, who called herself and Jim “two peas in a pod,” loved his outrageousness.

When Mary left for Mount Vernon College in Washington, DC, Molly and her father developed a ritual of sharing stories over wine and food when Mary returned for breaks. With Mary away, Jim initiated “Mystery Trips”—spontaneous flights to places like Palm Beach, with no luggage, paid for on the plane with a credit card. On these trips he was at his most fun, like a “fun brother/father.” But he could flip, resenting the cost, and he shared inappropriate sexual details that blurred the boundaries between father and daughter. Molly, as his primary emotional companion, didn’t know what was appropriate to hear or say.

When it came time to apply to college, Molly met with a counselor at Hawken who suggested only Ohio schools. Angry and dismissive, she threw the thick college guidebook down the hallway and decided to ignore his advice entirely. Her father left the application process to her. On her own, she found NYU’s Tisch School of the Arts, circled it, and decided that was where she wanted to go.

She auditioned in Chicago at a big hotel, where she saw other students preparing for Yale and Juilliard auditions. She performed a dark monologue from Agnes of God for Evangeline Morphos, head of the NYU Drama Department. Mid-monologue, a safety pin holding up her corduroys popped open and stuck her in the stomach, adding to the intensity. She knew she’d done well, and she was accepted. When the big envelope arrived, she couldn’t believe it. She and her father celebrated by watching Ciao! Manhattan, a film about Andy Warhol’s scene starring Edie Sedgwick, and Molly imagined her life in New York City would be cool, artsy, and creative.

Key Events

Molly skips achievement tests because her father would attach strings to writing a check
Jim Shannon encourages cheating and cutting school; takes Molly on outings to swing sets and coffee shops
Father compares Molly to Elizabeth Taylor from National Velvet
Molly and Mary drink at keg parties; father insists they call him instead of driving
Father buys Candie’s heels and mink coats; a librarian calls them “prostitute shoes”
Family visits Traxx, a gay bar; father parties with Alison and blocks a bar entrance with his car
Mary leaves for Mount Vernon College; father and Molly develop story-sharing rituals and Mystery Trips
Father shares inappropriate sexual details, blurring boundaries
College counselor suggests only Ohio schools; Molly rejects this and finds NYU Tisch herself
Molly auditions in Chicago with an Agnes of God monologue; safety pin mishap
Molly is accepted to NYU and celebrates watching Ciao! Manhattan

Character Development

Molly Shannon: This chapter shows Molly’s growing self-reliance. She learns not to ask her father for financial help because of the strings attached, and she takes full ownership of her college application process when the counselor dismisses her ambitions. Her audition—despite not even knowing what a monologue was—demonstrates both her inexperience and her determination. She knows she did well, and she’s right.

Jim Shannon: The chapter paints a complex portrait of a father who is simultaneously supportive and erratic. He encourages rule-breaking, buys glamorous gifts, and takes spontaneous trips, but he also resents costs, shares inappropriate details, and blurs boundaries. His love for Molly is evident, but so is his neediness—he relies on her emotionally in ways that aren’t appropriate for a parent-child relationship.

Mary: Though she leaves early in the chapter, Mary’s departure is significant. It shifts the family dynamic, leaving Molly as her father’s primary companion and setting up the Mystery Trips and the intensified codependency.

Alison: Molly’s friend who bonds with Jim Shannon, calling them “two peas in a pod.” She appreciates his boldness and outrageousness, offering a glimpse of how others saw him.

Themes, Symbols, or Motifs

Financial barriers to opportunity: The achievement tests require a check, not cash, and Molly’s babysitting money is “no good.” This small detail illustrates how class and family finances shape opportunity, even for a bright student.

Independence and self-reliance: Molly’s decision not to ask her father for the check, and later her solo navigation of the college application process, show her developing self-sufficiency.

Street smarts versus academic achievement: Jim Shannon explicitly values charm, social ability, and street smarts over grades. His philosophy shapes Molly’s upbringing even as she remains a disciplined student who earns As.

Father-daughter bonding through rule-breaking: Cutting school, Mystery Trips, and bar outings are all framed as bonding experiences, even when they’re inappropriate.

Glamour and appearance: The Candie’s heels, mink coats, and diamond ring represent a particular vision of sophistication that Jim Shannon wants for his daughters.

Blurred boundaries and codependency: The chapter is explicit about this—lines between father and daughter are blurred, and Molly is his emotional confidante.

Self-determination: Molly’s rejection of the counselor’s limited advice and her own discovery of NYU Tisch is the chapter’s central act of self-determination.

Leaving home and new beginnings: The chapter’s title “Leaving” points to Mary’s departure and Molly’s imminent move to New York.

Why This Chapter Matters

This is the chapter where Molly takes control of her own future. The college counselor’s dismissive advice—suggesting only Ohio schools—could have derailed her, but she rejects it and finds NYU Tisch on her own. The audition scene, with its safety pin mishap and her raw Agnes of God monologue, is a pivotal moment: it’s the first time she performs for a professional audience and knows she’s done well. The acceptance letter is the payoff, and the celebration watching Ciao! Manhattan frames her departure as an entry into an artsy, creative world. The chapter also deepens our understanding of her father—his love, his erratic behavior, and the blurred boundaries that shaped Molly’s childhood.

Study Questions and Answers

1. How does Molly’s father’s attitude toward academics shape her approach to school and opportunity?

Jim Shannon actively discourages academic effort, telling Molly to cheat on tests and cut school for outings. Yet Molly remains a disciplined student who earns As. His philosophy—valuing street smarts and charm over grades—doesn’t stop her from succeeding academically, but it does shape her independence. When the achievement tests require a check she can’t get without strings, she simply doesn’t take them, learning early that financial barriers and family dynamics can limit opportunity.

2. What does the chapter reveal about the relationship between Molly and her father?

The relationship is deeply affectionate but also codependent and boundary-blurred. Jim Shannon is a “fun brother/father” on Mystery Trips, but he also shares inappropriate sexual details and relies on Molly as his primary emotional companion. He buys glamorous gifts and encourages rule-breaking, but he can flip and resent costs. The chapter shows a father who loves his daughter intensely but doesn’t always know—or maintain—appropriate boundaries.

3. How does Molly’s college application process demonstrate her self-determination?

When the college counselor suggests only Ohio schools, Molly is angry and dismissive—she throws the guidebook down the hallway. Her father leaves the process entirely to her. On her own, she finds NYU’s Tisch School, circles it, and applies. She doesn’t even know what a monologue is, but she prepares one, auditions in Chicago, and gets in. The acceptance is a validation of her own judgment and effort, not her father’s or the counselor’s.