A confluence of personal, technical and business factors renders priorities, practices, and desires visible – and invisible – when people use online dating sites to look for partners. Based on a review of websites, interviews with dating site designer/developers, and interviews with would-be daters about their online experiences and their first dates, we offer some insights into the entanglement between daters, site implementers, and business models that is part and parcel of getting ‘matched’ via the Internet. We also examine the role of the website interface and match algorithms in the expression of the “real me” and the search for “the one” – and then how processes of self-presentation and partner imagination play into the planning, expectation-setting and experience of the first date. Finally, we reflect on issues raised for design and for strategic technology development. This study of online-offline encounters is an example of using detailed qualitative analyses to deliver deeper understandings of people’s experiences, offering a complement to large-scale, aggregated data summaries based on website activity logs and surveys.