This study explores positive youth development in terms of 5 C's (i.e. caring, character, competence, connection, confidence), self-esteem and psychological problems of undergraduate students in the United States and India. A sample of 47 participants (n= 22 American students and n=25 Indian students) was recruited from a university in the US and India. They completed a survey packet that includes questions and scales related to positive youth development, self-esteem and psychological problems. This study depicts a glimpse of an ongoing collaborative research project based on the US and India. Results showed significant differences between the two nations on the dimensions of caring and competence of positive youth development, as well as on psychological problems. It indicates that Indian students showed more caring attitudes and higher competence, although they experienced more psychological problems then their American counterparts. On the other hand, American students displayed stronger character, better connection, higher level of confidence and self-esteem as compared to Indian students. The findings will be discussed in the light of individualistic and collectivistic philosophy of society.