Under the British Mandate over Palestine, the British assumed the responsibility of tutoring the Palestinian nationalists toward the achievement of higher civilization, and as such, the British played the dual role of colonizer-patriarch. Yet there was something peculiar about the relationship between British officials and Palestinian nationalists. While many British officials depicted Palestinian nationalists (symbols of Palestinian virility) as indolent, disorganized, and immature, they also endowed nationalists with endearing qualities that may seem perplexing at first. But when examined in terms of the British colonizer-patriarch approach, it becomes evident that these male British officials forged a dialectical relationship between themselves and the Palestinian nationalists whereby the latter were made the necessary “other” in a predetermined show of male-dominated civilization. In effect, this emasculation would serve to prolong the British Mandate over Palestine under the premise that the Palestinian nationalists, in fact unfit to lead their people due to moral and virile inadequacy, were still in need of British assistance. As gender historians will argue, the deployment of femininities and masculinities in colonial discourse has been a means through which colonizers have endeavored to impose and maintain control over indigenous populations. So the question arises: to what extent can gender be incorporated into the relationship between male British colonial officers and male Palestinian nationalists in the first years of the Mandate? Through an examination of six British officials' memoirs from this period (1918-1925), and one Palestinian nationalist's memoir, I contend that this relationship was shaped by implicit (and occasionally explicit) prejudgments of masculinity and morality that would consequently serve to: 1) bolster the colonizers’ notions of heightened British virility (and therefore, civilization), and 2) crystallize the colonial legacy of establishing a permanently disproportionate relationship between the colonizers and the colonized. Therefore, with the inclusion of gender, and in the case of Palestine, imaginings of masculinity that were manifested in British ideals of leadership and camaraderie, this research offers an intriguing lens with which to reexamine this period in colonial history.