That Girl in Pinafore

In the 1990s Singapore, Jiaming juggles O-level prep with his parents' busy Dream Boat bar. The pressure of school and work strains his family and tests his loyalty to friends. The backdrop frames his early adolescence amid a bustling cityscape.

A reckless dare to obtain numbers from two girls leads Jiaming to meet May and the other girls, setting off a chain of awkward encounters. In the chaos, he bumps into May and drops his Xinyao booklet, a keepsake of his lost melodies. The spark of a connection is born from a moment of embarrassment and curiosity.

After the O-Level results, Jiaming contemplates quitting school, considering a different path. His friends push forward, and they all end up in the same Junior College as May and the others. The choice marks a turning point toward new ambitions and shared dormancy of dreams.

On the first day of JC, the group hatches a plan to start a pornographic magazine, leading to a month-long suspension. Jiaming keeps returning to the campus, drawn by the allure of a new social circle and the girl he’s beginning to care for. The incident sows early tensions and sets up future consequences.

In an empty assembly hall, May sits at the piano and plays the song from Jiaming's lost Xinyao booklet. A sudden interruption by bullies tests the limits of their budding bond. The moment binds their futures through music and shared memory.

A confrontation with bullies interrupts their growing closeness, with the attackers staking a claim on May. Jiaming is drawn into a tangle of loyalties and tensions among friends. The group must decide where their deepest loyalties lie.

Seeking a shared future, the friends form a band to enter a local Xinyao singing contest. They audition and cross paths with May, Jayley, and Hayley, uniting two groups into a single ensemble. The tempting prize of 5,000 dollars becomes a beacon for their dreams.

The band performs at a gig as bullies close in on May’s attention, but the audience keeps faith with them. Mid-performance, May collapses due to a heart defect, sending shockwaves through the group. The tragedy tests friendships and the limits of their dreams.

May's mother tries to pull May away from Jiaming, but the lovers’ bond deepens. Xiao Pang grows closer to Liyana, the driver’s daughter, adding warmth to the group’s dynamics. Subplots expand the ensemble’s emotional arcs.

May announces she must leave for the United States for health and future studies. On her birthday, she escapes the night to reach Jiaming’s house for a farewell, and the next day she departs with a bittersweet resolve to pursue her dream.

Jiaming travels to the United States to visit May, carrying money the friends pool together for her care. The trip becomes a poignant bridge between youth and distance, underscoring the depth of their shared history. After the visit, they return to Singapore to face the future and the Xinyao finals.

Months after the finals, May passes away, leaving the friends to mourn her loss. May's mother harshly rejects Jiaming, severing the last ties to that era. The tragedy marks the end of their first era and casts a long shadow over their lives.

Eighteen years slip by as the friends pursue separate lives: Cao Gen sells cars, Hao Ban runs a kopitiam, Xiao Pang becomes a dentist and starts a family, while Jiaming teaches English and builds a life with his own family. The Dream Boat’s memory lingers as a quiet undercurrent of youth. Their adult lives unfold with the ghost of May guiding their memories.

At the columbarium, Rachel Anderson arrives, claiming to be May's daughter and seeking her mother. The revelation unsettles Jiaming, forcing him to confront a new facet of his past and its lasting impact. The group watches history re-emerge in the present.

Rachel attends a performance the next day, and Jiaming invites his old friends to support her on stage. They perform together, weaving May’s memory into the fabric of their lives. The moment cements themes of love, loss, and enduring friendship that echo through time.