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Brandon Wade was a man with a stunted love life but a healthy bank account, two attributes that would lead him to establish seekingarrangement.com. Launched in 2006, seekingarrangement.com is a dating site that offers its members a path to forging 'balanced' and 'mutually beneficial' relationships. With an estimated 4.5 million active members across 139 countries, the platform connects wealthy men - or Sugar Daddies - looking for companionship, and younger women - or Sugar Babies - seeking consideration in the form of gifts, rent or tuition payments, international travel or simply cash. The site encourages university students in particular to join, and whilst it is couched as an introductions site, arrangements are usually understood to include sexual contact. Is seekingarrangement.com emblematic of shifting attitudes abetted by rapidly advancing technology, or a 'grey area' of online entrepreneurialism that is blurring into a highly policed 'red light zone'? This case is part of ANZSOG's Regulating the P2P Economy series. This series comprises a 'backgrounder' outlining key aspects of the P2P sector, significant areas of concern and some of the challenges facing regulators, and three high profile company examples (Uber, Airbnb, and Seeking Arrangement). Instructors can use this case on Seeking Arrangement in various ways. It can be used as a standalone example of the impact of a disruptive service delivery platform and the key public policy issues being generated. It can be used to illustrate and expand on specific issues by pairing it with the 'backgrounder' case as preparatory reading for students, especially those not overly familiar with P2P platforms. It can also be used for contrast and comparison discussion with the other company examples in the series (Airbnb, Uber) or, alternatively, instructors can pair the case with an organisation or situation of their own.