In this paper, we present a method of Dialogical Sketching. We introduce the development of this method as a discursive aid to understanding design probe responses within participatory co-design engagements but also articulate its potential more broadly within participatory research. Situated within a research study into the potential of digital jewellery to support self, we focus on how sketching can elucidate reflection on layers of meaning conveyed both explicitly and implicitly in participants' probe responses. The method enabled an iterative dialogue not bound by certainty, but more by inference, interpretation and suggested meanings. Systems of sketching scaffolded conversations about personal issues and feelings that were difficult to articulate in a way that was imaginative, rather than descriptive. We argue that the method firstly enriches the potential of probes, secondly encourages discourse in open and often uncertain ways and thirdly can enable sustained participatory engagement even through challenging circumstances.