In the Late Elizabethan Period, factionalism complicated the notion of, especially, male friendship. The scarcity of financial resources of the royal patronage, the arbitrary distribution of favours, and bottom-up pressures of patronees further problematized a healthy relationship among patrons and patronees and among friends. The horizontal and vertical social relations were to be conducted within theatricality; by performing a certain social role, while keeping one’s real ideas as confidential as possible. Deception and hypocrisy were necessary in order to survive verbal and non-verbal means of factionalism, which targeted, especially one’s reputation. This, however, problematized the perception of the reality of social behaviour. Friendship should be about sincerity. Yet, that sincerity was usually nonexistent in the overall pattern of Late Elizabethan theatrical behaviour that lacked demarcated lines between essence and appearance in a clear-cut way. Published or unpublished examples of advice literature, therefore, urged a thorough analysis of the behaviours of friends to instrumentalise them in utilitarian ways. One ought to be careful in choosing friends, who should both give support and provide advice. One should also be careful in rejecting double-dealers and flatterers. The problems to meet practice and theory led to many shifts of allegiance, double-dealings, and the lack to differentiate between advice and flattery. In Shakespeare’s Elizabethan history plays, the reign of King John, the Hundred Years War, and the Wars of the Roses found in chronicles provided several conflicting sets of values about the notions of friendships that were adapted to contemporary phenomena in the Post-Armada Period. Whether seen as plays or read in quarto versions, the plays reinforced the perception of friendship as performance liable to be a matter of appearance rather than essence. Therefore, this article will analyse the notions of friendships in the Late Elizabethan Period in Shakespeare’s history plays and illustrate how factionalism problematized those notions.