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Even in the “Good Old Days,” Dating Was Never Quite Easy
The Saturday Evening Post was out with a light-but-knowing piece today reminding us of something we tend to forget when we’re feeling nostalgic: even in the 1960s, dating was tough. Their feature, “Cartoons: The Dating Game,” leans on the old truth that a good cartoon can say in one picture what the rest of us need a whole conversation to admit. Beneath the jokes and the exaggerated situations is a familiar, very human theme—courtship has always been awkward, confusing, and occasionally a little humiliating, no matter what decade you grew up in.
What the Post is really doing, in its own gentle way, is taking a pin to the balloon of the idea that romance used to be simple and effortless. We like to picture the ’60s as sock hops, drive-ins, and steady girlfriends waiting by the phone. But the cartoons point to the other side of it: mismatched expectations, nervous small talk, the pressure to impress, and the silent worry that you’re doing it all wrong. The clothing and slang may change, but the feeling—wanting to be liked, wanting to belong, wanting to find someone who sees you—is as old as any love song on a jukebox.
And what’s striking is how cleanly the humor travels across time. The Post’s whole point, really, is that the dating “game” has always had rules nobody fully understands and referees nobody can find. In the 1960s, people navigated it with different manners and different assumptions, but they still bumped into the same walls: uncertainty, pride, misunderstandings, and the occasional bad break. The laughs come easily because the situations still ring true, even now, when a phone call has been replaced by a swipe and a text that can sit unanswered like a little storm cloud.
📺 Jack's Thoughts: I think pieces like this matter more than we give them credit for. We spend a lot of time today talking about how modern life has complicated everything—especially relationships. And yes, some of it truly has changed. Technology has moved fast, expectations have shifted, and the culture often feels like it’s shouting instead of talking. But there’s something grounding about being reminded that our parents and grandparents weren’t living in a romantic postcard. They were ordinary young people trying to figure it out, hoping not to look foolish, hoping to find somebody decent, and hoping their heart didn’t get stepped on in the process. It also makes me appreciate the quiet social strengths that used to surround dating, even when dating itself was hard. In simpler America—from the ’50s through the ’80s—you didn’t just have romance; you had a community that tended to know your name. You had church basements, bowling leagues, family friends, front porches, and neighbors who’d keep an eye out. That didn’t guarantee a happy ending, but it gave young people a kind of guardrail. Today, plenty of folks are dating in a world that feels more isolated—more private, more performative, and sometimes more disposable. The old cartoons don’t solve that problem, but they do remind us that people have always needed the same things: patience, humility, decency, and a little courage. If anything comes next from a piece like this, I hope it’s a little mercy—mercy for ourselves, and mercy for the younger folks trying to navigate modern dating without as much guidance as they deserve. The past wasn’t perfect, but it did understand something we ought to keep: love is serious business, and people’s hearts aren’t toys. Maybe the hopeful takeaway is that if dating has always been tough, it’s also always been survivable—and, for many, it has still led to lasting marriages, strong families, and the kind of companionship that makes an ordinary life feel rich. There’s still time to rebuild the habits that make commitment more likely: showing up, speaking plainly, treating people with respect, and remembering that a good person is worth the wait.
Read the full story at The Saturday Evening Post →
Jack Reynolds, wishing you a quiet evening and a brighter tomorrow.
— Jack Reynolds