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The US online dating sector is worth $2billion and has 5.5 million active registered users. This successful industry, however, is plagued by several cybercrimes that pose serious problems for dating service providers and users worldwide. Most research has addressed online scams and identity theft, which are just some of the cybercrimes occurring at dating sites. This paper moves beyond this limited scope and examines seven crimes: scams, identity theft, extortion, bot fraud, hacking, bogus dating sites, and fraudulent dating sites. The theoretical framework for this paper borrows from individual, environmental, and organizational criminological theories. Document analysis is conducted on 72 documents collected from dating sites, news and media sites, anti-scam commissions, law enforcement agencies, and government agencies, from 2000 to 2013. The paper examines 18 case studies of online dating crimes and uses a criminological approach to examine organizational dynamics, modus operandi, techniques, routines, skills, and motivations. The paper concludes by examining the problems in several existing online dating security, introduces a criminological approach to cybersecurity policy, and offers suggestions for further research.