Online courtship practices and the nature of virtual relating have been evolved within the last decades thanks to the introduction of hypermediacy, ubiquitous computing, location awareness, and geosocial tagging that creates an information shadow atop existing physical places that leads to augmented reality. Both material and digital inform each other and viewing online and offline as two separate realms might be ineffective in generating meaningful discussions regarding online matchmaking. Primary research question guiding both video and master’s thesis is How does the plurality of available online intimate partners influence the exclusivity of cyber-love? Implications of the romantic exclusivity in love online are, then, discussed with an autoethnographic research focus through disintegrating the components of exclusivity as to Privacy, Attention, Availability of Partners, Distraction, Multi-Conversing, Commitment and Online Infidelity. Then, new media cases related to Internet Art, Interdisciplinary Research, Blogging, Social Networks, Performance, and Experiment are included along with an extended discussion of the M.F.A. Thesis Project, which in return create hypertextual surfaces of relating and loving in digital postmodernity.