Learned helplessness is an important psychological construct that may influence senior tourists' subjective wellbeing while travelling. Employing a mixed-method approach and a multi-sample design, this study examines how Chinese senior outbound tourists’ perceived travel constraints and negotiation efforts affect learned helplessness in outbound travel. We identified four perceived constraints (perceived incapability, lack of suitable travel agencies and services, lack of information and personal support, and complex travel decision-making) and three negotiation strategies (seeking family support, physical/health preparation, and learning). Multiple regression analyses showed that among the four perceived constraints, only perceived incapability increased learned helplessness significantly; conversely, negotiation in general reduced learned helplessness. However, not as expected, negotiation was not founded to be a moderator between perceived constraints and learned helplessness. Theoretical and practical implications are also discussed.