This can, of course, be a wonderful thing: It is essential for our journey to heaven, and is the reason for the holiness of marriage. But when the men represent falsity it can also be horrendously twisted, as in the attempted homosexual rape in Sodom (Genesis 19) and the rape of the concubine in Gibeah (Judges 19). In a general sense, men represent things of the intellect -- facts, ideas, knowledge, everything from the deepest truths to the most pernicious falsities about life and the Lord. Women in general represents things of affection -- desire, passion, caring, everything from the most exalted love for the Lord to the darkest hatred. When a man “knows” a woman in the Bible, then, it represents a joining together of those intellectual and affectionate faculties. “Know" is also often used in connection with virginity. A women who has “not known a man” represents the affection for truth, unsullied by falsity.

In Matthew 23:23, this is explained by the Lord right there, in the verse.