These are the first two verses of a message offered by Wisdom and her associate, Understanding (:4-36). They’re depicted as ladies in the street calling out to those passing by (:2-3), apparently with a particular focus on “men” (:4-5).
The imagery is deliberate — Lady Wisdom and Lady Understanding are in public, accessible, and available to anyone interested in their assistance.
While it’s probably true that us guys need a lot more help than girls do(!), the reason it reads this way is because this section of Proverbs is a series of messages from father to son, It’s guy talk and, consequently, these two character qualities are personified as ladies.
The specific audience these ladies are addressing is the “simple” and “foolish” — regular characters in Proverbs. These aren’t mentally deficient guys, just naive about life — more importantly, about the ways of God.
Our verses indicate that what Wisdom and Understanding have to offer is exactly what each of these guys needs most. To the simple it’s “gain prudence” (literally “understand prudence”) — a word with both negative and positive connotations.
Used both as “crafty” (the Serpent in the Garden; Genesis 3:1) and as “sensible” or “discerning” here. I like the idea of “street smart.” A guy can learn to be “street smart” about the ways of God!
For the fool, “understanding” is offered (literally an “understanding heart”). The Hebrew concept of understanding involved cause-and-effect. It’s the ability to “realize how right choices lead to a meaningful life.”
All this just translates into good old “spiritual street smarts” — about life, about God!
Forrest Gump’s momma once said, “Stupid is as stupid does!” But it doesn’t have to stay that way!