The primary objective of this research was to determine if a specific set of contemplative practices enhance the underlying dispositions for critical thinking. The set of contemplative practices included mindfulness practice extended into journal writing, listening, inquiry, and dialogue. Taken together, this set of practices became contemplative interaction. Qualitative results showed increased self-confidence, engagement with multiple points of view, and an unexpected sense of connectedness that was stronger between students who disagreed with each other than between students who found easy agreement in their interaction. Quantitative results showed statistically significant gains in the average number of indicators for critical thinking dispositions appearing in student journals. Students’ sense of connectedness was based on taking an uncertain journey together and risking the suspension of beliefs long enough to be challenged. Connectedness supports critical thinking that is more focused on deeper and broader understanding than winning an argument. It opens the door to respect, empathy, and compassion: reason in service of the heart.