With the rise in the housing market, and profitability in new developments, historical architectures in Vancouver have been lost, erased, and replaced. These economically-driven developments are sanctioned by the city's administration. Known as 'Vancouverism' this trend creates in the experience of the urban dweller, a sense of loss in tradition, belonging, and identity. This thesis proposes to challenge these rapidly changing urban concerns, exploring how new living experiences might engage with and adapt to Vancouver as an urban playground. To break this cycle of Vancouver's current urban transformation, we will propose speculative architectural interventions and installations with programs that are conceived through the lens of apertures and ruptures - continuities and playful interruptions. This thesis proposes a recto-verso conversation between fact and fiction to challenge the current condition in Vancouver. It dreams to re-think the urban vernacular in Vancouver by engaging its citizens in a world of livable fantasies.