That Girl in Pinafore

In the 1990s, a group of young students navigates exams, friendships, and first loves against the backdrop of a bustling Singapore where a family’s bar, the Dream Boat, looms in the background. Secondary school student Jiaming Daren Tan is balancing his O-levels with his parents’ bar duties, while his friends Cao Gen Seah Jiaqing, Hao Ban Kenny Khoo, and Xiao Pang Kelvin Mun juggle schoolwork and their own schemes. A reckless dare to obtain the numbers of two nearby girls—Jayley Jayley Woo and Hayley Hayley Woo—sparks a chance encounter that ends with Jiaming bumping into May Julie Tan and dropping his Xinyao booklet.

After the O-Level results, Jiaming contemplates dropping out, a decision that sets him on a path alongside his friends who push forward. They all end up in the same Junior College as May, Jayley, and Hayley, and on their first day they hatch a plan that lands them in trouble: they start a short-lived pornographic magazines business and receive a month’s suspension. Despite the setback, Jiaming keeps returning to the college to hang out, and it is there that he is drawn to a familiar melody. In the quiet of an empty assembly hall, May sits at the piano, playing the very song from his lost Xinyao booklet. A confrontation with bullies interrupts the moment, thrusting Jiaming into a tangle of loyalties and tensions with the bullies, who claim May as theirs.

As the group pieces together their futures, they learn of a local Xinyao singing contest with a tempting prize of $5,000. Jiaming suggests forming a band with his friends, and after auditions they cross paths with the girls who also tried their luck but faced technical difficulties. The decision to join forces leads to a collaborative band that performs at and helps promote Dream Boat, blending their youthful ambitions with the dream of a shared future. The music becomes a thread that ties them together as they navigate adolescence, ambition, and affection.

Yet romance and rivalry color their days. During a gig, Jiaming finds himself relentlessly pursued by a group of bullies led by James, whose fixation on May complicates the band’s dynamics. The performance nevertheless carries on, but tragedy interrupts the momentum when May collapses—diagnosed with a heart defect. May’s mother warns her away from Jiaming, but the teens’ bond deepens, and May’s mother’s resistance only sharpens their connection. Amidst the strains, Xiao Pang grows closer to Liyana Sherly Ng, the driver’s daughter who helps him with Chinese lessons, sealing a tender subplot within the larger story.

Disaster and distance finally arrive when May announces she must leave for the United States. On her birthday, May disappears from school and is kept at home by her mother, who urges May to end things with Jiaming. Yet May escapes in the night, sprinting through the rain to reach Jiaming’s house, and the two spend the hours together before she departs with the next day’s flight. The farewell is bittersweet, with May’s mother handing May her backpack and May whispering that studying in the United States is something she must pursue, even if it means defying her mother’s wishes.

Jiaming visits May in the United States with money the group pools together, and upon his return the friends perform at the Xinyao finals. Months later, May passes away, and Jiaming and his friends mourn her deeply, only to be dismissed by May’s mother with a harsh slap and a shove out of her life.

Eighteen years pass in a quiet, present-day arc. Cao Gen has moved from the Dream Boat’s shadow to selling cars; Hao Ban runs a kopitiam; Xiao Pang becomes a dentist and is happily married to Liyana, with two sons in tow. Jiaming, meanwhile, pursues English Literature and becomes a teacher. He marries and raises a daughter named in memory of May, keeping her memory alive through small rituals like visiting her grave on the 18th death anniversary. It is at the columbarium that a new thread enters: Rachel Anderson, an American-Chinese woman who believes she is May’s daughter. She arrived in Singapore seeking her mother and, through a surprising revelation, confirms that she is the fruit of May’s love for Jiaming after their overseas connection.

The revelation moves Jiaming to tears as he wrestles with the reality of Rachel’s identity and the life she has built without him. Rachel’s visit to a performance the next day becomes a public, emotional moment that links the past to the present. Jiaming invites his old friends to support her on stage, and the gathering culminates in a poignant scene when Rachel sings, joined by Xiao Pang, Liyana, and the rest of the group who carry the memories of what they once shared. The performance—framed by memories of May and the enduring power of friendship—brings the story full circle, underscoring how choices from youth echo through the years and how love, loss, and legacy can shape a life long after the final curtain.

Last Updated: October 03, 2025 at 06:48