While in Syria from June 2009- July 2010, I became interested in two seemingly distinct phenomena. First, everywhere I turned, I was confronted by the so-called “marriage” crisis. Syrian youth, suffering from underemployment and economic stagnation, are by all accounts unable to marry. Urgency and frustration, often of a sexual nature, colored the daily talk of the young people. Schemes for marriage, for promotion, for love affairs were the subject, hashed and rehashed and rehashed again. Among my acquaintance, only one solution seemed consistently viable: emigration. Indeed, the overwhelming response to my questions about what people planned to do next in their lives was “In Syria, nothing.” Alongside marriage talk, schemes for emigration played a constant refrain. You can’t it would seem, stay Syrian and move into economic, social, and sexual seniority. Second, in the political imagery that “clutters” the Damascene public (Wedeen 1999) President Bashar al-Asad continues to be depicted as son (to Hafiz al-Asad) and brother (to Basil al-Asad). Months into my stay, an offhand comment by a Syrian friend of mine suggested the possibility of a third ‘phenomenon’ bridging the first two. Joking about the former president’s dominance of the symbolic landscape and his son’s relatively weak showing, my friend became suddenly grave. “Poor guy,” he said. Surprised, I later realized that his comment resonated with a general trend. With few exceptions, my friends’ tended to speak of the president in sympathetic, emotionally-laden tones. “I feel so sorry for him,” they’d say. Or: “He has such a burden.” Meanwhile the image of the father – usually articulated as “before” or “then” or in the “other regime” – worked contrapuntally. Here – at the intersection of the discourse of a sympathetic Bashar al-Asad, burdened by the faults and fames of the father, and the stymied Syrian “shab” – underemployed, unmarried, publically virginal – I make my intervention. Based on field notes, Arabic-language newspapers, and television serials, I contend that masculinity and manhood provide one critical lens through which to understand the interaction between the official political discourse and a certain kind of meaning-making on the part the Syrian shab. I argue that Bashar al-Asad, as a son, is portrayed as both ‘less than’ and ‘burdened by’ the image of the father. Asking why a hindered or “lessened” masculinity speak to a Syrian public I explore how generational burden, as a discursive trope, translates into both an emotionally-wrought political inertia.