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 ...

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