At various points in my Christian life, I’ve felt my cheeks burn with shame as I’ve faced my sin. I’ve felt humiliated, disappointed, and sometimes disgusted with what I’ve done.

Perhaps you’ve felt a similar anguish. You can’t believe those ugly words just came out of your mouth. You look back with a sense of embarrassment over how you acted so foolishly toward your parents. You’ve all but despaired over some ongoing sin that you cannot seem to confess.

As Christians, we have all looked at ourselves and felt sorrow over sin. But have we ever deeply considered why we do it in the first place? Why do we sin?

Searching Our Past Sins

In Confessions book 2, Augustine (354–430) probes for an answer to why we sin by considering moments in his own life. But he does so cautiously, clarifying that he looks back on his past sin “not for love of them but that I may love You, O my God” (2.1.1). He does not peruse past sins like we muse over old photos on our phone, but rather, like a doctor dissecting tissue to locate a cancerous tumor, Augustine remembers sin in order to discover its root cause. With Augustine, we should gaze at the darkness of past sin only to better understand our own hearts and, most importantly, to see the brightness of Christ’s mercy more clearly.

Augustine takes us back to his teenage years when his “delight was to love and to be loved.” Yet he “could not distinguish the white light of love from the fog of lust” (2.2.2). As he recounts how his “youthful immaturity” swept him away into “the madness of lust,” we expect him to stop and analyze the sinful motives behind his lusts. But he doesn’t. He turns instead, almost abruptly, to a very different kind of teenage sin: stealing pears with his pals as a prank (2.4.9).

“Behind every sin — from pride to greed to anger — is a perverse desire to imitate God.”

Augustine labors to understand this seemingly trivial sin to such an extent that some have worried he veers into scrupulosity. Yet he is not troubled with doubts about whether he sinned, as the overly scrupulous are. Rather, he struggles with understanding why he committed the sin at all. What motivated his teenage self to steal with such senseless disregard for God’s law against theft (Exodus 20:15)?

Why Steal Pears?

Augustine makes clear right away that the problem with his theft of the pears was that the pears themselves were not the problem. He had no desire for the pears. The pears were not lovely, and he had even better ones back at home. Nor did he steal because he was hungry: he and his buddies just threw them to the pigs after they had stolen them. So, why did he do it? Why steal something you don’t even want and won’t even use?

Before Augustine describes two motives for why he stole the pears, he considers what usually entices us to sin: disordered desire for otherwise good things. Our attraction to beauty, our delight in physical pleasures, and our satisfaction in success all become distorted when we love them apart from God. Like the prodigal son demanding his inheritance so he could run from his father (Luke 15:11–32), we sin when we spurn the Giver and selfishly love his gifts.

We can discern in disordered desires a certain logic to sin, even to a heinous sin like murder. Augustine points to Cataline, the archetypal Roman villain, to underscore that even in committing murder “he loved some other thing which was his reason for committing [his crimes]” (2.5.11). In our selfish pursuits, we may even commit murder to get what we want or protect what we’re afraid to lose.

But in Augustine’s case, he wasn’t motivated by a nefarious goal beyond the robbery or by distorted love for the sweetness of the pears. Rather, he says, he desired the sweetness of sin itself.

For the Thrill

When he considers why he stole the pears, he first says his “only pleasure in doing it was that it was forbidden” (2.4.9). The reward of the theft was not the pears but the stealing itself — “the thrill of acting against [God’s] law” (2.6.14). Augustine discerns something deeper in the thrill, though, than the racing heartbeat and giddy delight of getting away with a prank. Behind the thrill is the same desire to “be like God” that drove Adam and Eve to sin (Genesis 3:5). Even in rebellion, Augustine says, man is “perversely imitating [God]” (2.6.14).

Behind every sin — from pride to greed to sinful anger — is a perverse desire to imitate God. Pride, for instance, “wears the mask of loftiness of spirit,” even though God alone is high over everything (2.6.13). Greed hungers to possess more than it should, yet God possesses everything. Sinful anger seeks vengeance, but God alone can justly avenge. Therefore, we find a certain thrill in the forbidden precisely because, in pretending to be omnipotent, we perversely imitate God.

Such a perverse desire to be godlike, though, is not satisfied with sinning solo.

For the Fellowship

Our perverse imitation of God wants an audience. Augustine insists (three different times) that “I am altogether certain that I would not have done it alone” (2.8.16). “Perhaps,” he pauses to consider, “what I really loved was the companionship.” But no, he finally concludes, “since the pleasure I got was not in the pears, it must have been in the crime itself, and put there by the companionship of others sinning with me” (2.8.16). Augustine suggests that the good desire for fellowship with others, which symbolizes the ultimate fellowship enjoyed by God in his Trinitarian relations, becomes a perverse desire when it leads us into sin.

“Discovering the insanity of sin turns us back to the immeasurable mercy of Christ.”

These two motives — the thrill of transgression and friendship with fellow sinners — intertwine to move him to steal the pears. They go together because the feeling of a pretended omnipotence is consummated by the praise of others. The thrill of stealing, then, was not enough to motivate Augustine’s sin. Companionship adds the pleasure of praise to the thrill of the theft and becomes, in Augustine’s words, “friendship unfriendly” (2.9.17).

Yet, in naming these two motives, Augustine does not believe he has explained fully why he stole the pears.

Our ‘Complex Twisted Knottedness’

Even as Augustine lays out the two reasons for his theft, he asks himself, “What was my feeling in all this?” He wonders along with the psalmist, “Who can understand his errors?” (Psalm 19:12 KJV). Augustine recognizes that, at bottom, sin is persistently perplexing. Even a relatively trivial sin like a prank leaves Augustine uncertain about the root motive. Augustine’s analysis simultaneously reveals man’s desire for God even in our sinning and acknowledges man’s inability to explain why we pursue that desire for God by turning away from him.

What is finally inexplicable, then, about our sin is not that we sin without reasons but that those reasons do not ultimately make sense. Any attempt to peel back the layers of sinful motives ends in futility because identifying an original motive for evil is like trying to “hear silence” or “see darkness” (City of God, 12.7). We cannot see what is not there or hear what does not sound. Augustine points to a perverse imitation of God as the driving motive behind all vices, but why we desire to perversely imitate God in the first place is ultimately inexplicable.

Augustine feels the anguish of his inexplicable root motive when he exclaims, “Who can unravel that complex twisted knottedness?” (2.10.18). His anguish echoes Paul’s exclamation, “Wretched man that I am! Who will deliver me from this body of death?” (Romans 7:24). Like Paul, Augustine looks to Christ’s mercy (Romans 7:25).

Discovering the insanity of sin turns us back to the immeasurable mercy of Christ. Just as a child who has made a mess of his problem runs to his parent for help, so too we must run to God for mercy from the mess we’ve made. We will not do that, though, if we don’t feel the desperation of our situation. The whole of Confessions, says biographer Peter Brown, is “the story of Augustine’s ‘heart,’ or of his ‘feelings’ — his affectus” (Augustine of Hippo, 163). In the story of stealing the pears, Augustine feels — and helps us feel — the anguish of our inexplicable decision to turn away from God. He shows the depths out of which we cry to God for help.

Prodigal’s Return

In our sin, we need the desperation of the prodigal son who, after he squandered all his inheritance, recognizes his only hope is to return to his father (Luke 15:17–19). Or like the psalmist who calls to the Lord for mercy from the abyss of his sin (Psalm 130:1–2), we too must turn to God with hope-filled pleas for mercy. “For with the Lord there is steadfast love, and with him is plentiful redemption” (Psalm 130:7). We have been led by the insanity of sin to run from our Father, but he is ready and eager to run to us, brimming with forgiveness.

Augustine’s final paragraph draws us away from the darkness of our sin to gaze, by the mercy of Christ, on the beauty of God’s holiness:

Who can unravel this most snarled, knotty tangle? It is disgusting, and I do not want to look at it or see it. O justice and innocence, fair and lovely, it is on you that I want to gaze with eyes that see purely and find satiety in never being sated. With you is rest and tranquil life. Whoever enters into you enters the joy of his Lord; there he will fear nothing and find his own supreme good in God who is supreme goodness. (2.10.18; trans. Boulding)

God’s full forgiveness restores us to rest with him forever. So, as you search your past or present sins, find hope in your Father’s “plentiful redemption.”