Dung Gwok-man and Aak-syu are both clowns working at a Shanghai nightclub. With the onset of the Second Sino-Japanese War, Gwok-man, fueled by a sense of patriotism, decides to join the military. Amidst the chaos of Japanese aircraft bombing Shanghai, he crosses paths with a young girl, Aak-syu, as they take refuge under Suzhou Bridge. Their fleeting romance leads them to promise each other they will reunite at the bridge once the war is over. However, ten years later, Gwok-man returns to Shanghai, only to find himself amidst a sea of homeless veterans, with no trace of Aak-syu.
Now, Aak-syu has transitioned to working as a dance hostess at the Bat-je-sing nightclub. One fateful day, she encounters Dang-zai, a scatterbrained newcomer to the city who has just been robbed of her money. In a moment of kindness, Aak-syu allows Dang-zai to stay with her, unaware that their upstairs neighbor is none other than Gwok-man. As events unfold, Aak-syu's young maid is harassed by a stranger, leading Aak-syu to intervene and ultimately suffer for it. In a whirlwind of absurdity, she is unexpectedly pushed onto the stage to perform a song, catching the eye of a wealthy businessman who expresses a desire to marry her. However, Aak-syu defiantly rejects his advances.
In a twist of fate, Dang-zai inadvertently becomes the winner of a beauty contest dubbed "Calendar Queen," mistakenly believing it to be an interview for a teaching position. The contest sponsor, a wealthy elder, chooses Dang-zai for her plain appearance, hoping to prevent her husband from being enthralled by a more attractive contender. Meanwhile, Gwok-man’s song, "Shanghai Blues," becomes a beloved hit performed by the renowned singer Zau Siu-sin, capturing the heart of the city. During a particularly rainy day, Aak-syu and Gwok-man share an umbrella, stirring old emotions and leading them back to Gwok-man's home. However, this reconnection is interrupted by Dang-zai, who harbors unreciprocated feelings for Gwok-man.
As their paths intertwine further, Gwok-man and Aak-syu take on street performing to promote a new gift shop. One day during a performance, Aak-syu steps out of the shop after receiving gifts from a wealthy patron, who is demanding in return for his generosity. This encounter rekindles their connection, but a mishap leads to Gwok-man injuring Aak-syu's leg while trying to impress her. The situation escalates as Dang-zai attends a party celebrating her title of Calendar Queen, only to face the unwanted advances of a powerful man. In a comedic blunder fueled by the wealthy sponsor's drunkenness, a case of mistaken identity leads to chaos and mischief, ultimately resulting in an unexpected reunion for Gwok-man and Aak-syu.
As Aak-syu grapples with her feelings for Gwok-man and her realization that Dang-zai also loves him, she decides to leave Shanghai. In a heartfelt twist, Gwok-man races against time to catch up with her as she boards a train, determined to rekindle their relationship. Meanwhile, Dang-zai, heartbroken by their departure, encounters another woman who bears a striking resemblance to her, hinting at new beginnings on the horizon.
