What does Proverbs 23:27 mean?

In the prior verse, the reader was encouraged to keep their eyes on a godly example. This verse trades on that metaphor. Sexual sin often starts with the eyes (Matthew 5:28). Failing to care for where one looks can be as dangerous as being careless about where one steps. The imagery here parallels other proverbs which speak of sinful temptations as traps (Proverbs 5:22; 7:22–23; 22:14; 28:10). Even in the modern world, narrow voids are dangerous because they so easily catch persons off guard. To trip over a divot is risky enough; to fall into a deep cavity can be fatal.

The Hebrew phrasing of this verse implies the entire category of sexual temptation. The two examples represent what modern persons might distinguish as "fornication" and "adultery." The "prostitute" summarizes those who deliberately tempt others for money, or sport. The "adulteress" represents those who betray others in their sin. Whether the tempter is married or unmarried, both offer something spiritually deadly. Similarly, the literal phrasing refers to women tempting men; the principle applies to any person regardless of gender. Sexual sin violates God's design for intimacy. It also brings tremendous risks, both physically and socially (Proverbs 6:27–35).