A qualitative approach to investigating the content differences of trustworthiness of respondents in individualistic and collectivistic countries was undertaken. A total of 229 Canadian (male: 119, female: 110) and 112 Taiwanese (male: 54, female: 58) undergraduate participants responded to two open-ended questions: 1) “A trustworthy family member is someone who is or will...” and 2) “A trustworthy friend is someone who is or will...” Canadian participants responded in English and Taiwanese participants responded in traditional Chinese. To assess differences of trustworthiness descriptors in these two roles across cultures, and to retain the cultural nuances in the responses, content analyses were conducted on the responses in their original languages. Several notable similarities and differences emerged across cultures and referents. Participants from both Canadian and Taiwanese samples characterized trustworthy family members and friends as having integrity, using descriptors such as honest, reliable, truthful, and keeping secrets. In the Canadian sample, trustworthy friends and family members were described as being non-judgmental; additionally, a key descriptor of a trustworthy family member was loving, while a key descriptor of a trustworthy friend was loyal. In the Taiwanese sample, key descriptors of trustworthy family members focused on providing a safe-space and being unconditionally accepting; while the length of the relationship was a key condition of trustworthiness assessments of friends.