The article seeks to challenge the standard accounts of how to view the difference between Husserl and Frege on the nature of ideal objects and meanings. It does so partly by using Derrida’s deconstructive reading of Husserl to open up a critical space where the two approaches can be confronted in a new way. Frege’s criticism of Husserl’s philosophy of mathematics (that it was essentially psychologistic) was partly overcome by the program of transcendental phenomenology. But the original challenge to the prospect of a fulfilled intuition of idealities remained and was in fact encountered again from within the transcendental analysis by Husserl himself in his last writings on geometry and language. According to the two standard and conflicting accounts, Husserl either changed his earlier psychologistic program as a result of Frege’s criticism, or he was in fact never challenged by it in the first place. The article shows instead how Husserl continued to struggle with the problem of the constitution of ideal objects, and how his quest led him to a point where his analyses anticipate a more dialectical and deconstructive conclusion, eventually made explicit by Derrida. It also shows not only how this development constitutes a philosophical continuity from the original dispute with Frege, but also how Frege’s critique in a certain respect could be read as an anticipation of Derrida’s deconstructive elaboration of Husserl’s phenomenology.