Methods: A parallel mixed-methods study on 20 patient–caregiver dyads in an Asian population was conducted to explore the differential perceptions and barriers to ACP in dementia. We recruited English-speaking patients with mild dementia and their caregivers. A trained ACP facilitator conducted ACP counseling. Patient–caregiver dyads completed pre–post surveys and participated in post-counseling qualitative interviews. We used mixed-methods analysis to corroborate the quantitative and qualitative data. Differential perceptions of ACP were reported among dyads, with caregivers less inclined for further ACP discussions. Post-ACP counseling, caregivers were significantly more likely to acknowledge barriers to ACP discussions than patients (57.9% versus 10.5%, p = 0.005). Results: Thematic analysis of the interview transcripts revealed four themes around barriers to ACP: patient-related factors (transference of decision making, poor cognition and lack of understanding, and dis-inclination to plan for the future), caregiver-related factors (perceived negative impact on the patient, caregiver discomfort, and confidence in congruent decision making), socio-cultural factors (taboos, superstitions, and religious beliefs), and the inappropriate timing of discussions. Conclusions: In a collectivist Asian culture, socio-cultural factors pose important barriers, and a family-centric approach to initiation of ACP may be the first step towards engagement in the ACP process. For ACP in dementia to be effective for patients and caregivers, these discussions should be culturally tailored and address patient, caregiver, socio-cultural, and timing barriers.