Josh Sundquist has his left leg amputated from the hip after being diagnosed with cancer as a child.

Sarah Stevens agrees to be Josh's girlfriend after he works up the courage to ask her at church youth group.

Sarah breaks up with Josh just 23 hours after they start dating, sending word through her friend Eileen.

Josh convinces his conservative Christian parents to let him transfer from homeschool to public high school.

Liza Taylor Smith passes Josh a handwritten note through a friend, saying she hopes they will meet soon.

Unable to join the pumpkin race at Liza's Young Life group because of his prosthesis, Josh decides she is out of his reach.

On the last day of junior year, Josh asks Francesca Marcelo out using the line 'we should hang out sometime.'

On a golf date with Francesca, Josh falls over and his prosthetic foot turns completely backwards, humiliating him.

Despite spending the whole summer hanging out with Francesca, Josh never finds the courage to kiss her.

Josh asks Evelyn Williamson, who has an on-off long-distance boyfriend, to be his prom date.

On a canoe trip, Josh confesses his feelings to Lilly Moore; she tells him she has a crush on someone else.

Josh meets Sasha Wright, a Miss America contestant, at a school leadership conference and they exchange numbers.

Josh travels to the Miss America pageant to surprise Sasha, but she is cold and never contacts him afterward.

Watching a film about a character losing a limb, Josh cries in a parking lot and realizes his own self-doubt caused his failures.

After initially hesitating, Ashley Samsonite agrees to be Josh's first official girlfriend, and later his fiancée.

After having his leg amputated due to childhood cancer, Josh Sundquist grows up self-conscious and desperate to prove himself worthy of love. His earliest attempts at romance—with Sarah at church youth group and Liza at public high school—are derailed by his inability to see past his own sense of inadequacy. In high school and college, Josh repeatedly fails to pursue the girls he is attracted to, losing chances with Francesca, Evelyn, and Lilly through hesitation and fear. His post-college confidence leads him to pursue Sasha Wright, a Miss America contestant, but a key misunderstanding ends that connection too. A moment of painful self-reflection in a parking lot reveals that his own belief in his unworthiness—not his disability—was always the true obstacle. A transformed Josh pursues Ashley Samsonite with newfound persistence and finally achieves his lifelong goal of having a girlfriend.

The major milestones of Josh's lifelong quest for a first girlfriend.

Josh's childhood friend Tony remains his steadfast companion throughout his cancer treatment and leg amputation.

During a church camping trip van ride, Sarah Stevens is asked in truth-or-dare whether she likes Josh, and says no.

At the church group talent show, Josh's pastor awards him the superlative 'Most likely to ask what are we going to do next.'

Before starting public high school, Josh memorizes every classmate's name and face from a yearbook.

Josh's parents refuse to let him take Liza to the homecoming dance, warning that girls get pregnant at such events.

After their golf date, Josh and Francesca begin meeting twice a week at her house to play pool.

Josh engineers a plan for a romantic rooftop picnic with Francesca but their schedules never align.

The night before senior year starts, Josh attends a punk-rock concert with Francesca but still fails to kiss her.

At prom, Josh loses the Prom King vote to a popular football player named Joseph Chuk.

At prom, Josh uses his prosthetic leg's extended range to perform a standing split and wow the crowd.

Josh and his friend Brad sneak into a fraternity party where a girl named Paulette shoves Josh's hands away on the dance floor.

Josh calls Lilly Moore every single day during the summer after she rejects his romantic confession.

A girl named Stella begins following Josh's schedule and appearing everywhere he goes, making him deeply uncomfortable.

Shortly after turning 20 without ever having been kissed, Josh asks his friend Katie for help and they share his first kiss.

A stranger at a bar offers to buy Josh a drink after learning his leg will never grow back; Ashley handles the moment gracefully.

While Josh's big romantic milestones define his story, the secondary scenes around them reveal how deeply his environment shapes his insecurities. From his loyal childhood friend Tony to his sheltering parents who forbid homecoming dances with fabricated warnings, Josh's world is both supportive and stifling. His summer with Francesca is built on pool games and near-kisses that never happen, while prom with Evelyn ends in a spectacular party trick that still cannot win her heart. In college, Josh's obsessive daily calls to Lilly, his first kiss with Katie, and his unnerving encounter with a girl who stalks him all paint a picture of his emotional immaturity and slow-growing self-awareness. Each secondary moment quietly adds evidence to the investigation Josh will later undertake, revealing the recurring patterns behind his romantic failures. The story closes with a small but significant victory: Ashley's ease in handling a stranger's clumsy comment about Josh's disability signals she is the partner he has been searching for all along.

The smaller but telling moments that quietly shape Josh's romantic journey.

At age 25, Josh learns from his friend Dan that Charlotte, who he thought was his girlfriend, already has a boyfriend.

Josh discovers through Instant Messenger that Sarah Stevens has a crush on him.

Josh meets Sarah at a Starbucks and learns she had a crush on him but panicked and cried when they became a couple.

On his first day of public high school, a classmate trips Josh for walking with a limp.

Josh bumps into Liza Taylor Smith at a mall and concludes from her response that she was never romantically interested in him.

Francesca's father tells Josh's father there is no young man he would rather have his daughter out with.

When Josh asks Francesca during their investigation meeting why they never dated, she turns the question back on him.

During the investigation, Evelyn confesses she had a huge crush on Josh and waited for him to ask her out during her breakups.

Josh's college friends admit they had already assumed Lilly put Josh in the friend zone before he attempted the DTR talk.

A drunk friend spots Lilly at a bar and shouts at Josh that she is his girl, drawing Lilly's attention.

When Lilly later asks Josh about the bar incident, he lies and denies he still has feelings for her.

Josh sends Lilly a Facebook message asking for closure; she replies that she cannot remember their conversation at all.

During their long phone calls, Josh opens up to Sasha about his amputation and why he stopped wearing his prosthetic leg.

When Josh meets Sasha for his investigation, she reveals she wanted him as her boyfriend, but is now engaged to someone else.

On their second date, Josh spontaneously kisses Ashley instead of letting another romantic opportunity slip away.

Josh's investigation into his romantic failures is driven by a series of revelations—some delivered by the women he once pursued, others uncovered through painful self-examination. From the prologue's wake-up call about Charlotte to a Starbucks meeting where Sarah admits she had a crush but panicked and cried, Josh learns that the truth behind each rejection is far more complicated than he imagined. His encounter with Liza at the mall and his meeting with Francesca both confirm that he was the one who gave up, not the women. The investigation reaches its emotional peak when Evelyn confesses she had a huge crush and waited for Josh to act, and Sasha reveals she wanted him as a boyfriend but is now engaged to someone else. These revelations, combined with Josh's growing willingness to open up about his disability, finally crack his defensive mindset wide open. The pool ends with Josh kissing Ashley without hesitation on their second date, proving that his capacity for connection was always there.

The discoveries and emotional shifts that reshape Josh's understanding of himself and others.