Research on the role of the homestay in developing linguistic and intercultural competence among foreign language learners in study abroad settings has yielded contradictory results. While some studies captured some gains and a reasonable level of satisfaction, others chronicled experiences fraught with disappointment, frustration and limited progress in proficiency. What happens when you add diglossia to the mix and make the linguistic environment not only bilingual but multilingual? This study set out to address this research question in the Arabic context by examining the experiences of 73 American college-level students who completed two-month programs in Tunisia. Students were placed with local host families while attending an intensive Arabic program that taught Modern Standard Arabic along with some Tunisian dialect. All families were diglossic and bilingual if not multilingual, in addition to possessing varying degrees of familiarity with other Arabic dialects and so was the case with a large number of the students. This paper reports on the language choices in this complex linguistic setting during interactions between host families and guests. A look at post-program linguistic proficiency and intercultural competence reveal counter-intuitive outcomes and challenge the zero-sum game in which multilingualism and multidialectalism have been cast vis a vis foreign language development.