Distributed teams have become increasingly prevalent. However, distance brings challenges in practice, and chief among them is the development of trusting and cohesive relationships. By contrast, in co-located settings, informal social interactions beyond purely task-oriented communication support trust and cohesion building. This research fills the gap by exploring, in two related studies, how to use online playful activities to encourage informal social interactions at work and at a distance. The first study identifies the potential to use open-ended, freeform drawing to jumpstart trust, cohesion, and positive emotions in a distributed team setting. The results reveal that there are four core facets of the experience afforded by online playful activities: expressivity, reflection, interactivity, and playfulness. These results suggest that designing around the four facets could contribute to an engaging playful experience that would help teams build a common ground, support subjective affective expressions and experience, build up team knowledge in a relaxing social context, and promote positive emotional contagions. Thus, a prototype based on these findings was developed and tested in a short-term, in-situ study with five teams from industry contexts. The prototype supported asynchronous, anonymous, collaborative online drawing. We found that participants obtained an increased engaging experience and perceived trust, cohesion, and transient positive emotions over five days. Findings also identified the relationship between the four facets; namely, how each was influenced by the others. Based on findings from the two studies, as well as insights from previous, related research, we developed a theoretical model to capture the characteristics of online playful activities for distributed teams. This model leads to a design framework with eight concrete design guidelines that form a basis for system design for online playful activities for distributed teams.