Why learners return from study abroad (SA) with varying degrees of second language (L2) gains or differing attitudes towards the target language and culture remains an open question. This study employs theories of identity (Kinginger, 2013) and investment (Darvin & Norton, 2015; Norton Peirce, 1995) to examine the case of three learners of Spanish as they studied abroad in Spain. Interviews, journals, and language-use surveys were analyzed to understand how and why these learners’ investment in Spanish and in language learning opportunities shifted throughout their program. Pre- and post-SA speaking abilities tests in Spanish were used to measure how participants’ investments related to their L2 speaking development. The three case studies suggest that participants negotiate competing and fluctuating desires, identities, and investments that often lead to contradictory behaviors regarding their language learning and use while abroad. These opposing investments and identities stem from participants’ expectations of an idealized SA experience and their belief in the capital (Bourdieu, 1986) that Spanish may offer them back home and abroad. This study further finds that participants’ ongoing investment in learning and using Spanish relates to their L2 speaking gains post-SA.