My paper will present a reading of ‘Ala al-Aswani’s novel Shikaghu (2007) that is informed by the literary encounter with America in Arabic that stretches back more than a century. As a novel that presents a large number of Arab characters who face a variety of challenges in adjusting to American life, Shikaghu closely resembles one of the earliest works of Arabic narrative prose set in America and filled with Arab characters, Hikayat al-Mahjar (Tales of Emigration, 1919) by ‘Abd al-Masih Haddad. Both works feature this cross-cultural encounter, and both engage this encounter through a wide cast of Arab characters, albeit Shikaghu features mainly Egyptian characters while Hikayat al-Mahjar focuses on population of Syrian émigrés at the turn of the century. I will argue that Shikaghu, despite its recent date of publication, is still essentially engaged in a literary project that stretches as far back as Rifa’ Tahtawi; namely, the evaluation and critique of the self through the encounter with the West. The particular encounter that I will analyze is the oft neglected encounter with America in Arabic literature, as its more popular counterpart, the Arab encounter with Europe, has filled thousands of pages. The American encounter in Arabic literature has seen a renewed vigor of late, as al-Aswani’s Shikaghu, along with Rabi’ Jabir’s historical novel Amrika (2009) and Mona Tahawi’s novel Brooklyn Heights (2010) will attest. Our understanding of these new works can only be enriched through a comparison of critiques, symbolism and imagery of America found in the earliest works of Arabic fiction set in America, penned in the early 20th century. The prominence of the Mahjar poetry from this period has cast as long shadow over the short stories written and published during the early part of the 20th century. This is unfortunate, as this poetry, innovative as it was, rarely engaged with America as a place, or with Americans as characters. My paper, through a pointed comparison of Shikaghu and Hikayat al-Mahjar, and a general contextualization of the literary history of the American encounter, will bridge gaps in time and explore the significance of some uncanny continuities of literary forms and themes.