Loneliness has recently been defined as a public health problem, and college students from various cultures are considered a vulnerable group. As college students must cope with new personal, social, and academic challenges, their perceptions regarding their entitlement from their environment, and their gratefulness for the assistance they receive, may make a unique contribution to their experience of loneliness. In the current study we examined the associations between loneliness, gratitude, and two types of entitlement (active and academic) among college students in two countries: Israel and Poland. A total of 313 Israeli students and 275 Polish students completed a series of questionnaires. The results indicated that Israeli students experienced lower levels of loneliness and academic entitlement, and higher levels of active entitlement and gratitude, in comparison to Polish students. The two types of entitlement and gratitude mediated the association between students' country and loneliness. Active entitlement predicted more gratitude, which predicted lower levels of loneliness. However, academic entitlement predicted lower levels of gratitude, which predicted more loneliness. Our focus on entitlement, gratitude, and loneliness offers insights into the understanding of the psychological and social dynamics among college students in two countries, with implications for theoretical understanding and intervention planning in higher education.