Social shopping enables people to share and discuss about shopping in collaborative shopping environments. While much work has focused on using social data to promote shopping, fewer works have examined the way people socialize in the context of shopping as a personalized collaborative activity. In this paper, we propose to use qualitative methods to gain insight into people’s perceptions, concerns, and challenges in social shopping-related activities. Based on the findings, our work may contribute to the design of future online shopping sites and social media platforms that improve user engagement and participation in social shopping interactions, as well as facilitating personalized shopping and social experiences in online communities.