Gregory the Dialogist

But whoever does not find his beloved, it remains that he arise and go about the city, that is, traverse the holy Church of the elect with mind and inquiry; let him seek him through streets and squares, that is, let him observe those walking through narrow and broad ways, so that if he can find any traces of him in them, he may search them out, because there are some, even of secular life, who have something to imitate in the practice of virtue.

40 Homilies on the Gospels, Homily 25 ↗

Bernard of Clairvaux

"Through the streets and squares I will seek him whom my soul loves" (Song 3:2). Still she understands as a little one. I think she supposed that he, having gone forth from the tomb, would have immediately gone into public, so that as usual he might teach the peoples, and heal the sick, and manifest his glory in Israel, if perhaps they would receive him rising from the dead, who had promised they would receive him descending from the cross. …

Sermons on the Song of Songs, Sermon 76 ↗

Robert of Tombelaine

Because indeed it burns with the greatest desire, and whatever it holds does not suffice, until it finds the beloved, it therefore adds the constancy of its searching. What do we understand by the city in this place, if not the Church; what by the streets of the city, if not all those who are spiritual? While they walk toward the Church with their whole heart, they hold to the narrow way by which they are led to life. …

Commentary on the Song of Songs, Chapter 3 ↗