This paper emerges from research conducted in 2011 when I interviewed 93 Arab American [mostly Muslim] transnational teenagers who were attending high school in their parents’ “homelands.” Contrary to my expectations, and to the findings of my prior research, Arab American youth reported having overwhelmingly negative views of what these places would be like prior to living in them. These “homeland imaginings” run in the opposite direction of that proposed by diaspora theorists, who largely speak of “collective memories, visions, or myths” of an imagined “ideal home” {Safran, 1991: 83-84] and positive, even romantic, imaginary constructions, even if “forced dispersal and (…) subsequent unhappiness” (Cohen 1997: 26) are part of the narrative. This paper will report and discuss the homeland imaginings articulated by 43 Palestinian American teenagers (ages 16-18) who were raised in the United States but living in the West Bank on an extended sojourn to their parents’ homeland. It then speculates on the reasons for the negative homeland constructions of youth in diaspora. Components of the proposed explanation include the power of the American and Arabic media – which show largely violent or negative representations that are reinforced in school-based and other social encounters ¬– to influence the homeland imaginings of young Palestinian Americans, and, the relatively diminished influence of family and ethnic community (which in decades prior was positive and inspiring) on these constructions. These latter changes are in turn explained by a number of global and historic factors, including the demise of the PLO and the rise of religion and global media. In the end, global media, especially television that is based in the Arab World — because it is watched and favored by their parents and understood by children in diaspora to accurately portray Palestinian reality — plays the most significant role in the construction of the homeland imaginaries of Palestinian American youth. The outcome is far short of ideal, positive, or romantic. This “problem” however, tends to be resolved upon having lived experiences in the homeland.