This article utilizes a Lefebvrian framework – specifically, his notions of “implosion and explosion”, the triad of the production of space, and his conceptions of “everyday life” and “oeuvre” – to comparatively engage two case studies alongside each other: urban South Chicago, and exurban North Carolina. Drawing from ethnographic (in-person and digital) observations and anecdotes, we suggest that these concepts are dynamically and flexibly applicable to the shifting terrains of urban and exurban relations and offer ontological pathways for productive comparison across difference. Conceptually, the article is also undergirded by Hochschild's (2016) notion of the “empathy wall”, a sociological barrier which divides polarized and socio-spatially- segregated geographies, within the context of recent urban and anti-urban insurrections and demonizations of one and other. These divides are viscerally evident in post-Trumpian America, but extend to many global contexts; thus, our comparison speaks to wider relevance. We argue that oppositional geographies like urban and exurban are inextricably linked and mutually constitutive, despite representing different sides of the “empathy wall” (in a political and cultural sense), and inhabiting distinct urban morphologies, geographical settings, historical lineages and political borders and boundaries. Furthermore, we suggest that such a relational pairing of urban alongside exurban is vital to overcome the seemingly insurmountable ontological, cultural and political borders between them. By reflecting on everyday life and social formations around ephemeral centers and sites such as cafés, backyard barbeques, lake parties and gyms, we offer some areas where dialogue and political solidarities might emerge across, and despite, the “empathy wall's” steadfast insurmountability.