Few perhaps need to be reminded as to how much Joyce`s writings influenced Derrida and how the latter`s philosophical enterprise known as deconstruction continued to draw its inspiration as well as strategies from the ``revolution of the word`` initiated by the former; indeed, the two essays explicitly foregrounding Joyce`s works (“Ulysses Gramophone” and “Two Words for Joyce”) constitute only a more overt testament to the pivotal position occupied by Joyce in the extended trajectory of Derrida`s thinking starting out from his initial essay on Husserl (“Introduction to The Origin of Geometry”) and culminating in his final 2003 seminar (“The Beast and the Sovereign, Volume II”), in both of which the Irish author receives more than a passing mention. Rather than, however, examining the proximity between the two representative figures of modern literature and philosophy in general terms, the present inquiry focuses on one central topic which apparently has never received proper attention hitherto: love. How does Joyce`s problematization of love in Ulysses, for instance, makes us rethink about Derrida`s flitting remark on the same topic in The Post Card? And how in turn does Derrida`s differential insight force us to reinterpret Joyce`s thematization? Though only coincidental at first, both writers` engagement with the topic will turn out to show that they have more in common as their respective approach attempt to reach the same end albeit from radically incommensurable tradition and geopolitical positionings.