Objective Reflective writing is an established method for teaching medical students empathetic interactions, though little is known about students’ reflections on connecting with patients during the clinical clerkship. The purpose of this study was to describe factors that medical students perceive contribute to or detract from making connections with patients and families, as identified in a writing assignment during the pediatric clinical clerkship. Methods Reflective essays submitted by third-year medical students about interacting with patients/families during their pediatric clerkship were qualitatively analyzed for thematic content. Results Major themes emerging in 44 essays analyzed included time, knowledge, language and culture, and actions. Barriers to connecting for some students were considered resources by others. Critical reflection was present in 31.8%. Conclusions Students’ perceptions of factors that influence their interactions with patients and families will enhance or detract their ability to make connections. Through reflection, medical students – amidst clinical responsibilities – can identify how, why, and whether or not connections with patients/families have occurred. Practice implications Recognizing what factors medical students perceive as enhancing and detracting from connecting with patients/families will help preceptors foster those connections and mitigate barriers. Future study could assess how to best provide specific individualized feedback to best enhance critical reflection. We recommend the inclusion of brief reflective writing exercises during clinical clerkships in medical school, as it may augment students’ ability to connect.