The collection centers on the courtship and domestic life of a larrikin named Bill and his beloved Doreen, capturing the vernacular spirit of early 20th-century Australia. Through a series of rhythmic verses, the protagonist navigates the social expectations of his class while attempting to win the affection of the titular character. The narrative framework relies on the 'sentimental bloke' persona, utilizing a distinct dialect that highlights the tension between rough-hewn urban life and the desire for romantic stability. The world is defined by the bustling streets of Melbourne, where the constraints of social status and the rigid codes of the local 'push' dictate the characters' interactions.

This work is widely regarded as a cornerstone of Australian verse, celebrated for its successful elevation of working-class speech into a literary form. The poems are often noted for their ability to balance lighthearted humor with genuine emotional resonance regarding the human condition. Readers frequently highlight the accessibility of the language and the enduring charm of the central romantic relationship. The collection remains a significant cultural artifact that provides a window into the social fabric of its time.