Contemporary philosopher David Benatar has advanced the self-evidently controversial claim that “coming into existence is always a harm.” Benatar’s argument turns on the basic asymmetry between pleasure and pain, an asymmetry he seeks to explain by the principle that those who never exist cannot be deprived. Benatar’s import is almost incredible: humans should cease to procreate immediately, thereby engendering the extinction of the species—a view known as “anti-natalism.” According to many of his readers, the ancient Hebrew sage Qoheleth expresses a pessimistic nihilism that runs as thick as Benatar’s. Prima facie grounding for this assertion is that Qoheleth, like Benatar, raises the issue of whether coming into existence may be a harm—and gives an affirmative answer. In two passages, Eccl 6:1–6 and 4:1–3, Qoheleth declares that an unborn hypothetical person is “better off” than their existent counterpart. Yet the meaning and implication of these words is far from obvious. Does Qoheleth imply that the non-exister’s state, and non-existence in general, is universally superior to existence? Or is he instead speaking exceptionally, of particular persons in rare circumstances? By examining the two “better”-statements in their literary context, I will argue that Qoheleth intends these examples as exceptions. He does not go so far as to make the supremely nihilistic claim that coming into existence is always, or even generally, a net harm; yet, he does concede that in certain cases, it can be. Beyond this, I will explore how the two thinkers’ divergent conclusions can be traced to a deeper difference of philosophical method. This question concerning non-existence opens a window to Qoheleth’s broader scheme of values and therefore serves as a surprisingly useful entry point by which to engage his philosophy. The paper utilizes the methodology Jaco Gericke has recently termed “philosophical criticism,” but specifically applied to Qoheleth.