This essay examines the images of the night in Shakespeare’s sonnets and in the poetry of Antara Ibn Shaddad. It explores how these two poets identify the night with sleeplessness, aloofness, loneliness, night birds, dreams, old age and death. Doing so, it suggests that the two poets, despite of their cultural backgrounds, and of the boundaries of place, language and time, use almost, with some differences, the same nocturnal motifs. This essay is important because it shows how different cultures follow strikingly similar, if not exactly perfect, ways of describing the darkness of nature as an echo of the darkness of the strayed soul. In the light of these strong affinities, this essay suggests two possibilities, one being the universality of these poets (Hereafter, I have, where possible, made references to some Western and Oriental poets who similarly use some image-clusters of the night.), and the other being that Shakespeare, in one way or another, may have been exposed to the poetry of Antara providing that it was translated into Latin or any other European language. No matter which one of these possibilities seems to be credible, this study tries to imply that cultures, regardless of language barriers, share some quintessential ways of expressing cultural innerness, to which researchers should pay more attention instead of being preoccupied with cultural differences as signs of clash of civilizations.