The word עֶ֫צֶב (generally translated “pain”) occurs only 7 times in the whole of Scripture, making it fairly easy to pin down its meaning based on context.  It is sometimes translated “sorrow” or “grief.”  The passages, for the sake of reference, are: Genesis 3:16; Psalm 127:2 (in the plural form); Proverbs 5:10;   10:22; 14:23; 15:1; and Jeremiah 22:28.

As these passages are all poetic, it seems that this term is one principally devoted to poetic language, so some variety is to be expected in its usage and semantic range.  In the Jeremiah passage, most translations yield “idol” rather than anything related directly to grief, sorrow, or heartache… but it might be argued that the worship of idols is a cause of such emotions for HaShem.

The word “pain” in Genesis 3:16 “And I will greatly increase your pain in child-rearing” is עֶ֫צֶב (‘étzev) in Hebrew… which means “emotional travail; heartache.” I think what it is really focused on is that parenting sometimes hurts.

There is no greater sorrow than that of a mother grieving for  her deceased child.  As the protoeuangelion (first iteration of the Gospel) precedes Genesis 3:16 by only 1 verse… it is possible that this verse is likewise prophetic, looking ahead to the grieving mother of Yeshua after the Execution Stake.

Scarlett Stough expounds:

Parents suffer for and with their children throughout their lives. The concern and empathy they feel does not end when their children grow up and leave home. The responsibilities may change and end, but the love never does.

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image information: “tear face” by e5ther (deviantart)