This article describes a lesson that uses the question, “Does Title VII’s prohibition on discrimination because of ‘sex’ include a prohibition on discrimination based on sexual orientation” as a means of teaching about the complexities of the legal regulation of business. This is a timely and important topic and may well reach the United States Supreme Court. The lesson involves numerous issues including statutory interpretation, jurisdiction, administrative law, stare decisis, separation of powers, the Commerce Clause and the Supremacy Clause. The case study also raises significant ethical issues and develops students’ ability to analyze laws from competing ethical frameworks. Because the case study involves a potentially controversial issue, the lesson requires students to discuss a divisive topic in a civil and respectful manner. Additionally, with the current focus on on-line and hybrid teaching at many universities, this is an example of how instructors can use online tools to further learning goals.