This chapter investigates the development of language learning motivation in 23 B2-level students of Italian from an American university during a Collaborative Online International Learning (COIL) project with seven C1-level English students at a university in Italy. Drawing from task-based assignments that focused on well-being and happiness in everyday life, this study analyzes the student artifacts of the project as well as video deliveries to illustrate the transformational process. The assignments are integral components of several disciplines, including educational pedagogy, intercultural studies, sociology, and psychology. Foremost, they served to analyze and evaluate language proficiency and its progression throughout the COIL project. By engaging in task-based assignments and cross-cultural communication, students demonstrated significant improvements in their ability to use the target language effectively. The artifacts and video deliveries provided clear evidence of enhanced fluency, vocabulary acquisition, and grammatical accuracy. Furthermore, the collaborative nature of the project fostered authentic language use, allowing students to internalize linguistic structures and develop confidence in their communication skills. This study highlights how experiential learning within an intercultural framework can serve as a powerful catalyst for advancing language proficiency while simultaneously nurturing broader academic and personal growth. Findings demonstrate how students’ pre-COIL motives (cultural, linguistic, and intellectual) were negotiated while participating in the COIL project. Through interacting with Italian students, the American students’ preexisting linguistic apathyLinguistic apathy was reversed by a positive reevaluation of their own oral skills, which enhanced their desire for higher proficiency, while the Italian students’ linguistic skills, which were advanced as English learners, improved threefold, allowing for colloquial, spontaneous conversations on both ends. The project also stimulated students’ intellectual motive to learn a foreign language using technology, leading to the creation of remarkable videos that enriched their cultural experience through a social and dynamic process. Topics such as food health, physical activity, mindfulness, digital detox, and the happiness map allowed participants to reflect on their personal habits, identify areas for improvement, and implement small, meaningful changes to enhance their overall well-being. These topics encouraged participants to adopt healthier lifestyles, foster mindfulness, and develop a deeper understanding of how cultural values influence happiness and self-care practices. As one participant reflected: “This entire experience was truly life-changing!” The purpose of this paper is to illustrate how the language learning motivations of students were negotiated through the lens of wellness and well-being topics while participating in a 7-week mobility-based COIL project.