The contemplation of proportion was once essential to understanding order in architecture. Analogy not only mediates between scales but is able to reinvent. The technique of analogy is explored in John Hejduk's Masques series, in which he envisioned the city as a theater of characters. For Hejduk, theater offered a model of mirroring a current state of society. Thus, he created a repertoire of characters that move from city to city, being both autonomous and part of a cohesive set. In my contribution, I put the idea of the Masques in analogy to the concept of the Velum from Leon Battista Alberti’s Treatise on Painting. This Play of Analogy constructs degrees of likeness and investigates similiarity in difference. It is followed by a proposal of reconciliation: the Ovidian Observatories that enact and circulate knowledge of transtemporal and transcultural mythic figures. Each figure stands alone yet interacts within a larger set. The setup wants to combine the intrinsic knowledge in painting, literature and architecture. The mediating instance, analogy, explores how a mythical figures can speak through spatial forms, considering how architectural elements can embody and store meaning. In adapting an investigative rationalism that balances intuition with AI's “common sense”, connections are drawn from myriad possibilities. The mechanics of analogy, finding meaningful relations between inherently incomensurable domains, manifests the difference between data and knowledge. The embodied interface suggests an ethical distancing in opposition to the act of identification and immediacy prevailing in the contemporary use of technology.