The Do-Over (miles High Club, #4)

The novel follows Christopher Miles, the youngest of four brothers who run the family media empire, Miles Media. At 31, Christopher lives in extreme privilege in London: penthouses, sports cars, and a revolving door of casual sexual encounters, often with more than one woman at a time. He has never had a girlfriend and has never been forced to discover who he is beneath his wealth.

His comfortable existence is upended at a quarterly board meeting when his older brothers, Jameson, Tristan, and Elliot, ridicule him for being emotionally stunted, noting he sleeps with women in pairs to avoid falling for any one of them. That evening, a date named Carly tells him he has no substance and that "diamonds are made under pressure" (12). A waitress later suggests starting fresh is like a "do-over" (14). Inspired, Christopher announces he is taking a year off to go backpacking under the alias "Christo" with only $2,000 and no access to his fortune.

Meanwhile, Hayden Whitmore, a 25-year-old specialist in cattle breeding from a 3,000-acre farm in Finger Lakes, Orange County, prepares for the same trip. Her high school sweetheart, Regi, left her two years earlier, and though she booked the journey after that heartbreak, she is terrified to go alone. Her mother, Valerie, and best friend, Monica, push her out the door.

Christopher arrives at BB Backpackers hostel in Barcelona, overwhelmed by bunk beds, communal bathrooms, and loud partying. He meets fellow backpackers Basil, who dispenses unexpectedly wise advice despite terrible hygiene, and Bodie, a friendly Australian. A disastrous one-night stand leaves him robbed of his entire bank account. Penniless, he meets Eduardo, a 14-year-old boy of Spanish descent who works nights at the hostel bar. Eddie bluntly advises him to "get a job" (47), inspiring Christopher to work as a taxi driver and fend for himself for the first time.

Hayden arrives at the same hostel. Her first interaction with Christopher is a clash, but a spark ignites at a full moon party when a game forces them to kiss. Hayden whispers that she has slept with only one person; Christopher admits he has lost count. The kiss is electric, but Hayden walks away, placing him firmly in the friend zone.

Six backpackers form a group for 12 months: Christopher, Hayden, Basil, Bodie, Kimberly, and Bernadette, a hostel roommate who harbors an unreciprocated attraction to Christopher. They work weekends in Barcelona and explore new countries during the week. Christopher deepens his bond with Eddie, buying him a new phone after the boy's breaks. Eddie refuses the gift, suspecting Christopher wants sexual favors in return. The reaction devastates Christopher and hints at the harsh realities Eddie has faced. Christopher preserves the boy's pride by having Eddie "work off" the phone as the group's translator.

Over months of travel, Christopher and Hayden develop an affectionate but platonic bond, spooning nightly and sharing intimate conversations. Hayden tells him she believes he thinks "nobody could possibly love you for you" (114) and challenges him to examine why he uses casual sex as armor. In San Sebastián, he asks her to kiss him in the ocean at three in the morning. She refuses, saying the man she wants will love her so much the thought of being with another woman would turn his stomach. Christopher whispers, "I could try" (145), which Hayden calls "probably the most unromantic thing I have ever heard" (147). They make a pact to return to this beach in 10 years.

On Hayden's birthday, Christopher gives her an engraved necklace and requests their song, "Halo" by Beyoncé. He quietly stops sleeping with other women. Their tension builds until a kiss leads to oral sex, but the next morning Christopher panics and flees to New York. He confides in his brother Elliot that he fears ruining the relationship. His mother, Elizabeth, produces a childhood therapist's notebook diagnosing him with a fear of failure so intense he refuses to attempt anything he might not excel at, including love.

After eight days, Christopher returns to Barcelona and tells Hayden, "Let's fucking do this" (200). They sleep together for the first time, and the encounter is both physically and emotionally transformative. In Croatia, three months later, he tells her he loves her, and she responds in kind.

The group takes a job on a luxury superyacht owned by Julian Masters, one of Jameson's close friends, forcing Christopher to conceal his identity while serving drinks to men who know him well. When Masters asks why he would endure this for a girl, Christopher replies that Hayden is not just a girl but "the girl" (275).

As the 12-month trip ends, Christopher reveals his true identity moments before a limousine arrives. On the private jet home, Hayden refuses to speak to him for nine hours. At his 60-floor New York penthouse, she explodes, refusing to sleep in his bedroom. After Christopher admits he should have told her sooner and explains he wanted to protect what they had, Hayden agrees to give London a three-month trial. They visit her farm, where her father, Harvey, is openly hostile. Christopher faints watching Hayden assist a difficult calving. When her ex Regi appears uninvited, Christopher throws him down the porch steps, and Harvey privately warms to Christopher, making him promise to put Hayden's happiness above his own.

In London, Hayden becomes miserable: isolated in the penthouse, hounded by paparazzi, unable to work, and deprived of the outdoors and animals she loves. Christopher works long hours and communicates through his assistant rather than directly with her. Their disagreement over where to live escalates into an ultimatum. He insists she honor the three-month commitment; she tells him that if sex matters more than her happiness, it is goodbye. They break up, and he drives her to the airport in tears.

During six agonizing weeks apart, Christopher spirals while Hayden returns to the farm but no longer feels at home. Christopher then learns from the hostel manager that Eddie is a homeless orphan whose mother died when he was eight. The boy has no surviving relatives, cannot read or write, and sleeps in an abandoned house. Christopher flies to Barcelona and tells Eddie he has come to take him home.

Both Christopher and Hayden independently return to Barcelona after Eddie's phone is stolen and they lose contact with him. Reuniting at the hostel, they agree that Hayden will stay with Eddie while Christopher handles the visa paperwork from London. Daily phone calls among the three gradually restore the intimacy between Christopher and Hayden, and she teaches Eddie to read and write. Hayden eventually tells Christopher she wants another chance, regretting that she did not try harder.

When Eddie's paperwork clears, Hayden brings him to London. Christopher drives them not to his apartment but to a country property with a sign reading "Bumfuck, Nowhere" at the gate: a farm he has purchased as a compromise between their lifestyles. Inside the candlelit house, he drops to one knee, telling Hayden she taught him how to love and showed him "it's okay to be coal" (445), completing the metaphor Carly introduced about diamonds and pressure. She says yes. That night, he tells Eddie they want to adopt him. Eddie accepts, and Christopher asks the boy to call him Dad. The novel closes with the three beginning life together on the farm, a found family forged from a year of travel, heartbreak, and transformation.