In the bustling heart of Chicago's LaSalle Street, the 111 West Monroe site presents a unique narrative of adaptive reuse, encapsulating the thesis of 'Multiplicity of Experiences.' This thesis ventures beyond the conventional restoration, aspiring to reinvigorate and repurpose two distinct architectural forms — a robust brick structure and its transparent steel and glass counterpart — through strategic cuts that foster gathering and community interaction. The manipulation of light at varying intensities becomes the silent choreographer of space, delineating zones of activity and orchestrating the human experience within these revitalized edifices. The old brick building, a testament to historical solidity, now breathes anew as student housing, offering challenges turned opportunities through its dense facade and muted interiors. In contrast, the steel and glass structure, with its morning light and open vistas, evolves into a sanctuary for families, children, and the elderly, promoting a sense of openness and interconnectivity. This architectural duality harmonizes to form a living, dynamic tableau that captures the multiplicity of human experiences, enabled by horizontal and vertical incisions that carve out communal and private spheres. The groundwork of the thesis is the concept of gathering — initiating with the public's allure into the retail and amenity spaces on the lower levels, ascending to the private residences above, and culminating in the shared terraces that bridge different age groups and backgrounds. This thesis demonstrates how spatial intervention, particularly through the nuanced application of light and the deliberate choreography of openings, can script diverse experiences from serendipitous encounters to orchestrated communal activities. It presents a model of adaptive reuse that not only conserves the structural essence but also injects a new pulse into the urban fabric, championing a symbiosis between the old and the new, the individual and the collective, the built and the unbuilt. Through the transformative act of cutting and layering, this study sheds light on the potency of architectural intervention in shaping human and spatial experiences. The result is a rich mosaic of life, where every stratum, every incision, every ray of light adds a verse to the narrative of gathering, from dawn's first light to the tranquil hum of evening, offering a blueprint for reactivating spaces that reach beyond their walls to touch the human soul. / Master of Architecture / This thesis explores adaptive reuse at 111 West Monroe, using architectural cuts to manipulate light and space, thereby creating a multiplicity of experiences that foster community interaction and rejuvenate urban life across diverse generations.