Critical pedagogy scholars have described teaching as an act of love. This love is not a trivial emotion but a conscious action that demonstrates care, respect, honesty, listening, and solidarity. However, translating love and other principles of critical pedagogy into the classroom can be complex and painful. This article discusses our pedagogical experiences of love and care inside and outside classrooms. Our reflections on working in a juvenile detention center and a food justice mutual aid project show how understanding love, care, and solidarity as actions have been essential for working with our communities. At the same time, our experiences pose questions about the complexities and possibilities of loving and caring in precarious and totalitarian circumstances. We contribute to thinking about the application of critical pedagogy beyond school classrooms.