Why is wisdom referred to in the female form?
I mentioned this in the first week of our series in Proverbs. There’s no particular reason why wisdom is personified as a female, as opposed to a male. The reason for the personification is to give wisdom some human characteristics so there’s some tangibleness to her. Wisdom can be a very ethereal and unreachable kind of idea for many. In giving wisdom human characteristics, the author of Proverbs helps us to understand and see what wisdom is really like and how to follow on her path in life.
How do I ensure that I will receive wisdom's spirit?
It begins by listening to her because those who listen to her call receive her spirit. Practically speaking, this begins by reading your Bible so you hear from the wisdom in God’s Word. Getting in a Life Group, where you hear wisdom voice through others, would be your next step because none of us listen to wisdom perfectly and need others to help us see where we’ve traveled down the path of foolishness. These folks will also confirm to you where you are listening to wisdom, which should give you assurance as to which path you are traveling on.
If wisdom is personified as a woman in this passage, but isn't a "real" person, how am I to understand her judgment?
"You don't want to get on wisdom's bad side, for she is a wrathful judge to all that ignore her."
Here’s what wisdom’s judgment means: If you ignore wisdom, you’re going to suffer the consequences of your choice. Before we talk about judgment, though, it’s best to look at wisdom’s grace. Wisdom tells us the wise way to live, the best choices to make, and how best to honor God. That’s grace! We don’t have to figure things out on our own.
The judgment wisdom gives to those who don’t listen are the consequences for living foolishly, making poor choices, and not living to honor God. So what does her judgment include? It can be as simple as “If you don’t look both ways before you cross the street you may get hit by a car” because biblical wisdom includes common sense. It could also include spiritual ideas such as “If you reject the grace of God you will not spend eternity in Heaven with Him.”
The judgment of wisdom is simply the consequences we experience for ignoring the wisdom God has given to us and revealed in His Word. And her judgment is fair to all who ignore her. But don’t forget her grace!
You mentioned Proverbs 8:27-31 about wisdom being there during creation. The connection was made to Jesus who was there with God, the architect at the foundation of the world. Verses 22 and 23 sound like wisdom was the first created thing before God began creating the heavens and the earth. Jesus was not the first created thing because he was always with God, whereas wisdom describes her creation. The end of the sermon described many ways that wisdom's call and God's call are alike and how wisdom's judgment and God's are final. In our life group discussion, there were questions about whether wisdom here is Jesus talking – possibly prophetic writing. Is wisdom meant to be a separate entity to Jesus?
Proverbs 8:22-23 "The Lord brought me forth as the first of his works, before his deeds of old; I was formed long ages ago, at the very beginning, when the world came to be."
I specifically skipped Proverbs 8:22-23 because that is where there are some obvious disconnects between Jesus and wisdom (as you state, Jesus wasn’t created like wisdom was). My point was to show that although the connection isn’t perfect, there is a God-like (Christ-like) voice to wisdom when she speaks after her long period of silence (chapters 2-7). It is a voice of judgment that is very similar to God’s voice of judgment (especially when Christ returns again). Commentators are split on how far we should take this connection. I tried to take the analogy as far as I could without stating that Wisdom and Jesus are the same. They aren’t the same. And wisdom isn’t even a person (or a separate entity). As I mentioned in the first sermon, wisdom is given human characteristics simply to make it a bit less mysterious and easier to understand.