Lin Pianpian was born into poverty. In the thirteenth year of the Chongzhen era (1640), she worked as an itinerant courtesan peddling her services on the streets of Twenty-Four Bridges' Willow Lane. By chance, she became acquainted with Fang Zhiyou, but gradually drifted apart from him after Su Lingyan's death.

Her exceptional beauty propelled her through multiple promotions in subsequent years. By the Yiyou year (1645), when demonic troops breached the city walls, she had already become the most renowned "celebrated courtesan" at Twenty-Four Bridges.