Pityriasis rosea (PR) is a benign papulosquamous disorder seen commonly in clinical practice. Despite its prevalence and benign nature, there are still times when this common disorder presents in an uncommon way or course posing diagnostic or management problems for the treating physician. The etiopathogenesis of PR has always been a dilemma, and extensive research is going on to elicit the exact cause. This review focuses mainly on the difficult aspects of this benign common disorder such as etiopathogenesis, atypical manifestations, recurrent cases, differential diagnosis, therapy and pregnancy considerations. Although we could not find a black and white solution to all these problems, we have tried to compile the related literature to draw out some conclusions.