Though it took place more than 50 years ago, this dialogue still resonates with the dilemmas of intermarriage in today’s industrialized world. Riding on a train, I [RLQ] overhear a middle-aged Spanish speaking woman telling another sitting next to her that she should discourage her son from dating an American woman. “They have another culture. They don’t believe in family like we do.” What differences are implied in this statement? What is the prevailing discourse about these differences and what dynamics result from them? Given the persistent trend of high rates of intermarriage among Latinos, are there alternative discourses of resiliency that can be learned from those who dare to go contra la corriente, against the current (Andrews, 2003; Bacigalupe, 2003)? In this chapter, we explore emergent themes in Latino-Anglo intermarriage regarding perceived intercultural differences. Intercultural differences are explored by looking at specific factors such as courtship patterns; ideas about family, language, and communications styles; and how couples make meaning about their differences. The values attributed to intercultural differences are often negotiated against the backdrop of the dominant culture and the current social and political contexts from which these differences emerge.