When a legal mind meets a human heart, the gray areas of work and life start to make a lot more sense. In this episode, Match Group’s Vice President of Global Employment Law and Ethics & Compliance, Katie Dugan, joins hosts Roxanne Petraeus and Melanie Naranjo to explore how love, law, and leadership collide. From the do’s and don’ts of dating at work to what really defines a “hostile” environment, Katie shares how empathy, judgment, and accountability can coexist—even in the most complex workplace situations. The trio dives into real-world workplace dilemmas, generational shifts in expectations, and the delicate art of handling the gray with both heart and integrity.