This essay argues that the short parable in John 16:21 is a double entendre, referring not only to a woman’s child-bearing experience in general but also to a specific woman’s child-bearing experience—her hour [ἡ ὥρα αὐτῆς], foreshadowed in this parable and realized at the foot of the cross in chapter 19, where Jesus announces that she has become a mother and he has become a human being through his death. The essay will first demonstrate that John 16:21 is a parable, surveying the relevant scholarly interpretations of the passage. In order to substantiate the double entendre in 16:21, the essay will demonstrate John’s regular employment of double-meanings throughout his Gospel, exposing and justifying a criteria by which to determine such meanings. Next, the essay will apply this criteria to John 16:21 showing the climactic double-meaning of the articular “mother” and how its Isaianic background also bears witness to this reading. Lastly, the essay will demonstrate that by recognizing this double entendre in John 16:21 readers of John tap into a mystifying merge of Jesus’ hour and his mother’s hour at the foot of the cross wherein Jesus becomes “the human being” and she becomes “the mother.” Such a reading, additionally, provides an overlooked parallel between John and the Synoptics: the Johannine birth narrative of the Fourth Gospel.