Empowered by the rich sensory capabilities and the advancements in artificial intelligence (AI), head-worn displays (HWD) could understand the user’s contexts and provide just-in-time assistance to users’ tasks to augment their everyday lives. However, there has been limited understanding of how users perceive interacting with AI services, and how different factors impact the user experience in HWD applications. In this research, we investigated broadly what user and system factors play important roles in human-AI experiences during an AI-assisted spatial task. We conducted a user study to simulate an everyday scenario where augmented reality (AR) glasses could provide suggestions/assistance. We researched three AI system factors (performance, initiation, transparency) with multiple user factors (personality traits, trust propensity, and prior trust with AI). We not only identified the impact of user traits such as the levels of conscientiousness and prior trust with the AI, but also found interesting interactions between them and system factors such as AI’s performance and initiation strategy. Based on the findings, we suggest that future AI assistance on HWD needs to take users’ individual characteristics into account and customize the system design accordingly.