A work from Philo’s maturity received some attention in last years as to the Jewish exegete’s ethnic affiliations. For instance, Maren R. Niehoff argued that De Vita Contemplativa and its long tirade against Greek drinking parties should be read in the context of Philo’s enlisting of the Jews with the ranks of Roman culture. Accordingly, Philo’s “us vs. the Greeks” diatribe belongs to claims of the intelligentsia of his Roman contemporaries, wherein the heritage of Old Greece as enlightenment agent to Barbarians had passed on to the Empire. What is more, this Roman ethos had more gravitas, more self-restraint, and frugality than the old Greeks. Philo’s description of the encratite symposium of his Jewish contemplatives is understood in this context of cultural war. It is within this polemic that we read Philo’s boutade against Plato’s Symposium (Vit. Cont. 57-64). From a critique of Greek drinking parties, Philo shifts to an assault on the philosophical symposia of Plato and Xenophon. These, he assures, are not models for posterity’s merry banquets. Philo’s attack focuses on the otherwise celebrated Socratic pedagogic pederasty. Following other Roman Middle-Platonists skeptical of a Socratic chaste philosopher uninterested in boy “tail-chasing” (paidiká/erōtōn thēra), — e.g. Cicero suspects all “seizing of Ganymede” erōs are mere excuse for “desiring of mundane kind!” (Tusc. IV.71) — Philo launches an attack on pedagogic pederasty and on Plato’s philosophical erōs. This paper maps out De Vita Contemplativa’s participation in the counterculture gaining momentum in the 1st c. CE which expressed disapproval of homoerotic ars amatoria, arguing love between a man and a woman was more spiritual than love between a man and a boy and describes how the Jewish philosopher derides of the idea that the contemplative man may fall in love — an ideal expounded by Platonists and Stoics alike. The paper further makes observations about how cultural war wants to make claims over sexual object-choice protocols.