Charles Ellicott Commentary Jeremiah 13:21

"What wilt thou say, when he shall set over thee as head those whom thou hast thyself taught to be friends to thee? shall not sorrows take hold of thee, as of a woman in travail?" — Jeremiah 13:21 (ASV)

What will you say? —The verse is difficult, and requires an entire retranslation.

What will you (the daughter of Zion) say? for He (Jehovah) shall set over you as head those whom you taught (=tried to teach) to be your familiar friends. This was to be the end of the alliance in which Judah had trusted. She had courted the Chaldean nobles as her lover-guides and friends (the word is the same as in Jeremiah 3:4; Psalms 55:13; Proverbs 2:17; Proverbs 16:28).

Another possible construction gives, shall set over you those whom you delight to be your friends as head over you, i.e., those whose supremacy Judah had acknowledged in order that she might court their alliance. What could come then but that which was to the Hebrew the type of extreme anguish (Isaiah 13:8; Isaiah 21:3; Psalms 48:6), the travail-pangs which were followed by no joy that a man was born into the world (John 16:21)?