Recently, there has been a clear shift in the Interaction Design community towards the design for engagement as opposed to more traditional ideals of efficiency and functionality. Our work explores how to design for aesthetic engagement in interaction; building on an approach founded on phenomenology, embodiment, pragmatist aesthetics and embodied cognition. In this paper, we present four different research through design projects we have undertaken, in which we leveraged this approach. These designs cover a wide range of contexts, scales and use. Together, they describe and open up a design space: each of the projects provides rich, aesthetic experiences that respect complexity and ambiguity. They entice people to engage with body and mind, where meaning arises in dialogue with the artifact. We present and critically reflect on these projects in the form of an annotated portfolio. Comparing and contrasting the project results reveals insights into our overall approach and research interest regarding how to design for engagement. We conclude with opportunities that these reflections offer for the design of engaging interactions. Furthermore, we expand on the implications that these reflections suggest towards further trajectories of practice-based research into such experiences.