A number of university students in the Philippines come from distant places of residence and often experience homesickness as they commence university life. The current study investigated the relationship of homesickness with academic engagement among freshman university students and the relationship of social connectedness with homesickness. In six universities in the Philippines, a survey was conducted among 304 freshman university students in their first two to three months of university attendance. Results showed that social connectedness was negatively associated the two dimensions of homesickness, and that homesickness negatively predicted cognitive and affective engagement. Results are discussed with emphasis on the function of social connectedness in attenuating homesickness, the potential detriments of homesickness on university students’ academic engagement, and the necessity of extending school counseling programs to also include goals in addressing homesickness and promoting social connectedness.