Part 1 is organized into two Chapters:In Chapter 1, I introduce the conceptual research outline and main contents of this thesis by unpacking my research motivation, background, related literature, main research goal and question, and the overall trajectory through a conceptual map. Then, I will recap all of these elements in the last section that explains the structure of this dissertation.In Chapter 2, I will unpack my research methodology by explaining the meaning of making artifacts ("Expressive Entities") in Research through Design (RtD) and summarize other methodological approaches in RtD. Then, I articulate concepts of practice-based research knowledge, experimental artifacts, and experimental making in RtD. Finally, "Experimental Making" will be introduced, which is used for constructing this dissertation, composed of three elements: Defamiliarization, Imagination, and Creativity .PART 2 is organized into two parts: In Chapter 3, I will represent a Design Research Program that draws a conceptual connection through my research motivation, concept, approach, design, and outcome to shape the main framework of this thesis, "Poetic Engagements with Technology".In Chapter 4 -Chapter 7, I will unpack the designed artifacts which refer to "Expressive Entities" and how they produce Four Poetic Interactions which are specified from the concept of poetic engagements.The following funding opportunities and supports have been contributed to creating my design work, "Expressive Entities" throughout the years."Tête-à-tête 22" has re-made for exibiting for Dutch Design Week, 2022, and has funded by Unversity of Twente. This is a collaboration with Daniel Saakes."Footsie" was conceived and created during two artist residency programs. -The table top during the artist residency-'subnet air' at HCI center, Salzburg, Austria, 2017 and the chair at the Pink, RiSE, Umea, Sweden, 2019. This is a collaboration with Daniel Saakes."Coffee with a Spider" has conceived and funded by the Asia Cultural Center during an ACC artist residency 2018, South Korea. It was completed by re-creating the table component and adding a lighting interaction to the chandelier in the Netherlands in 2023."Thou and I", "I Smile at You...", "Greeting", "Don't Talk to Me", funded by a Faculty Research Grant 2017 of Indiana University, South Bend. Some of the projects were developed at the Center for HCI, University Salzburg, Austria, during the "subnet AIR" artist residency in 2017.