I watched the last couple seasons of Mad Men in the same way that I sometimes gaze at sirens and scattered glass after a highway accident. I cannot look away from the heartache. There’s Don driving all the way to Racine, Wisconsin, to find yet another woman, Joan sitting in a velvet-posh restaurant with a man who’ll eventually leave her, and Roger slouched at the bar making snide remarks that conceal his discontent.

As I track all the drama and dysfunction of 1960s-era Madison Avenue, I want to pretend these characters are entirely different than me. I want to designate them as godless hedonists reaching out to touch the hem of a Gucci garment that shimmers for a while but is powerless to save them. I want to believe they’re lost simply because they don’t know God. But I know better. Setting aside the depressing aspects of their very secular, pseudo-glamorous lives, the condition they suffer from is universal: loneliness.

As a parent, especially, I find myself faced with the challenge of talking about loneliness in the context of Christian living. I can teach my kids how to eat their greens, wipe their bottoms, and greet new guests with civility. I can teach them that Jesus loves them. But somehow I also have to teach them about the “now, not yet” dichotomy that says yes, Jesus is among us, but he’s not here yet in fullness, so on this side of eternity we’re still vulnerable to the strong, silent undertow of loneliness—the same loneliness that leaves Don Draper looking wistfully out his window at the New York cityscape.

I worry in particular about my two daughters. Perhaps because they’re the older of my kids. Or perhaps because young women are often socialized to believe that once they marry, they can somehow escape a solitude that is ultimately inescapable, a solitude that marriage and even faith itself cannot (and should not) inure them to.

I spent most of my 20s as a single woman. After college, I moved into my own apartment and worked various jobs. Unlike my mother, who married at 22, and my grandmother, who married at 18, I was a single professional woman who came home to a dark and quiet apartment. On weekend nights, I hung my jacket on the back patio to air out the scent of cigarettes from the bar I’d been lurking in, then slumped down in a patio chair. Behind me rose the spires of one of the largest Gothic cathedrals west of the Mississippi and before me a city nightscape. Sitting in the darkness between the church and the world, I felt alone in a way that seemed both satisfying and terrifying.

By now, I’m in my late 30s, married with three kids and pregnant with a fourth, so I’m sitting on the other side of that uncertainty. But I’ve experienced loneliness in marriage, too (by no fault of my husband). Even motherhood can be a quagmire of solitude. A few months ago, I stood in the bathroom staring at a positive pregnancy test and crying, not because I resent babies, but because early motherhood for me is marked by severe social alienation, seclusion, and even depression.

Most of us experience circumstantial isolation at one time or another, but the real problem moves past the boundaries of situation or mood. No one—least of all we Christians—escapes the pain of loneliness. C. S. Lewis felt it after his conversion. Even Mother Teresa grappled with it for decades. Kierkegaard, too.

Saint Augustine wrote in The Confessions that “my heart is restless until it finds its rest in Thee.” If it were possible, I’d take the Bishop of Hippo out to a bar and over a frothy pint tell him that these now-famous words are a bit too tidy and perhaps a little untrue. Faith casts light on what would otherwise be a bleak and meaningless horizon, yes. But we’re not yet at the end of all things, and so to imply that rest (even rest in Christ) is entirely possible on this side seems to obscure what Mad Men reveals so well—that restlessness and loneliness are an undeniable part of the human condition.

Part of my job as a mother, then, is to push against deceptive social paradigms and teach my girls that regardless of their status—single, married, divorced, widowed, with or without children—they will face intense loneliness that has the potential both to break them and drive them further into faith. I don’t want them chasing after the ephemeral dreams of this world or believing that belief itself will insulate them from the pain of pilgrimage. Instead, I want them prepared—for steep mountains, deep thirst, and a long search for the only thing that will ultimately satisfy them: the full restoration of God’s created order.

In Orthodoxy, G. K. Chesterton says that if “the revolutionists of this age choose a god from all the gods of the world… they will find only one divinity who ever uttered their isolation,” who cried out to God on the cross, Why have you forsaken me? As my kids grow older, we’ll talk about how God himself experienced isolation in the incarnation. We’ll read Lamentations, Job, and the Psalms and study St. John of the Cross and his dark night of the soul. We’ll approach the church as a space where, through song and prayer and liturgy, we name our loneliness as part of our longing for heaven.

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And maybe someday I’ll show them an episode of Mad Men. When they watch Don Draper drive down the open road as the camera pulls back for a wide shot and the soundtrack swells, they might feel what I feel: a clutch in the throat. A yearning. A sting of loneliness that tells me I belong not to the City of Man, with its empty Midwestern roads and sad bar scenes, but, ultimately, to the City of God.

Andrea Palpant Dilley is the author of the memoir Faith and Other Flat Tires: Searching for God on the Rough Road of Doubt, which tells the story of her crisis of faith. She lives with her husband and their three kids in Austin, Texas. To connect with Andrea, visit her on Facebook.