There is downplay of interpersonal relationship in bureaucratic system of management around which most organisations are built, as popularized by Max Weber. But Human Relations thought led by Elton Mayo has been able to successfully advocate the recognition of interpersonal relationships as very important in employees’ work experience. From this reflection, came the urge to conduct a study about the “Factors of friendship formation and benefits as well as risks of workplace friendship using two tertiary institutions in Ibadan, Nigeria as case studies”. The theoretical framework of this study was social action theory. A descriptive design was adopted while a multi-stage sampling procedure was used to select samples. Survey and In-depth interviews were combined in gathering data for the study. The survey data were analyzed using descriptive and inferential statistical techniques while qualitative data were content analyzed. Results from the study revealed that, respondents, most of which were Yoruba (78%), Christians (82%) and married 82%, were neither influenced by their sex and occupational status nor by age ((p=.40, .33 and .08 respectively Sig at .05 level) about having workplace friendship. Friendship opportunity was discovered to be established in the public university much more than the private University (Sig .001) counterpart. Although, motivational and facilitating factors influenced formation of friendship at work, the benefits acted as main magnetic pull for friendships. Policy makers and management of organisation should embrace workplace friendship by creating opportunities for such and integrate it with formal relationship at workplaces.