The theory of realistic mathematics education establishes that framing mathematics problems in realistic contexts can provide opportunities for guided reinvention. Using data from a study group, I examine geometry teachers' perspectives regarding realistic contexts during a lesson study cycle. I ask the following. (a) What are the participants' perspectives regarding realistic contexts that elicit students' prior knowledge? (b) How are the participants' perspectives of realistic contexts related to teachers' instructional obligations? (c) How do the participants draw upon these perspectives when designing a lesson? The participants identified five characteristics that are needed for realistic contexts: providing entry points to mathematics, using “catchy” and “youthful” contexts, selecting personal contexts for the students, using contexts that are not “too fake” or “forced,” and connecting to the lesson's mathematical content. These characteristics largely relate to the institutional, interpersonal, and individual obligations with some connections with the disciplinary obligation. The participants considered these characteristics when identifying a realistic context for a problem‐based lesson. The context promoted mathematical connections. In addition, the teachers varied the context to increase the relevance for their students. The study has implications for supporting teachers' implementation of problem‐based instruction by attending to teachers' perspectives regarding the obligations shaping their work.