In part 1(0-15:50), the guys discuss the first major question about this book: Is Song of Songs truly wisdom literature?
Tim notes that there are multiple levels of interpretation. The most obvious one views Song of Songs as semi-erotic love poetry. While this isn’t wrong, Tim notes that a deeper reading can metaphorically map the man and woman’s sexual love for one another onto the human pursuit and quest for wisdom.
Jon says that this view of interpreting Song of Songs is new to him. The reason, Tim notes, is because modern biblical scholarship often tends to see only what it wants to see. Tim adds that multiple historical scholars note the double and triple meanings throughout the book.
In part 2 (15:50-33:30), the guys dive into the book. Tim outlines a few basic facts about the book: 
• The poems go back and forth between a man and woman: The man is called “king” (1:4, 12) and “shepherd” (1:7).
• The name “Solomon” is never marked as a speaker, and the main question is whether the lover (“my beloved”), who is called “king” and “shepherd,” is Solomon or a distinct figure. Notice the word “beloved” (dod, דוד), spelled with the same letters as “David” (דוד), who was both a king and shepherd (whereas Solomon was only a king).
• The woman is called “whom I love” and “the Shulamite” (which is the feminine of Solomon’s name. It would be similar in English to “Daniel” and “Danielle”).

Tim cites Roland Murphy:
“On one level, the [Song of Songs] is a collection of love songs. However, as edited [to be part of the Hebrew Bible], do these poems have a wisdom-character on another level of understanding? First, there is the fact that ancient Jewish tradition...attributed this work to Solomon (Song 1:1)... it was mean to be read as a work in the Solomonic wisdom tradition… [T]here is an affinity between wisdom and eros in the wisdom literature. The quest for wisdom is a quest for the beloved…. The language and imagery used to describe the pursuit of Lady Wisdom [in Proverbs 1-9] are drawn from the experience of love. The Song of Songs speaks of love between a man and a woman...it is by that very fact open to a wisdom interpretation. Wisdom is to be “found” (Prov 3:13; 8:17, 35), just as one “finds” a good wife (Prov 18:22; 31:10).... [Both] Wisdom and a wife are called “favor from the Lord” (Prov 8:35 and 18:22). The sage advises the youth to “obtain Wisdom,” to love and embrace her (Prov 4:6-8). The youth is to say, “Wisdom, you are my sister” (Prov 7:4), just as the beloved in the Song of Songs is called “my sister (Song 4:9-5:1)... It is precisely the link between eros and wisdom that opens the Song of Songs to another level of understanding. While it is not ‘wisdom literature,’ its echoes reach beyond human sexual love to remind one of the love of Lady Wisdom…” (Roland Murphy, The Tree of Life: An Exploration of Biblical Wisdom Literature, pp. 106-107.)
In part 3 (33:30-47:00), Jon notes with this interpretation that the female character is the “divine” character. In most popular interpretations, Solomon is closer to the Christ figure, and the woman is as the Church—making the male the “divine” character.
Tim then dives into the literary design of the book. The Song is designed as a symmetry (see the work of Cheryl Exum and William Shea).
The Literary Macrostructure of Song of Songs:
1:2-2:7 Mutual Love
B. 2:8-17 Coming and Going
C. 3:1-5 Dream 1: Lost and Found
D. 3:6-11 Praise of Groom 1
E. 4:1-7 Praise of Bride 1
F. 4:8-15 Praise of Bride 2
G. 4:16 Invitation by Bride
G. Acceptance and Invitation by Groom and Divine Approbation
C. 5:2-8 Dream 2: Found and Lost
D. 5:9-6:3 Praise of Groom 2
E. 6:4-12 Praise of Bride 3
F. 7:1 Praise of Bride 4
B. 7:11-8:2 Going and Coming
8:3-14 Mutual Love
(Chart by Richard M. Davidson)
Tim points out that the first half explores the engagement, passion, and constant desire and pursuit of the lovers, though their embrace is cut short multiple times. The second half mirrors the first, but this time