Shakespeare typing Hamlet. JFK on a cellphone. Elvis using Twitter. Each is an anachronism, the technical term for a chronological blunder.

Many years ago I went with my family to see Elizabeth Taylor in Cleopatra. As young as I was, I gave up on the movie in utter disgust when Cleopatra winked at Caesar. I didn’t care that the filmmakers were having a little fun with their presumably sophisticated audience. To me, it was a deal breaker.

In HBO’s Boardwalk Empire, set in Atlantic City during Prohibition, loving care and great expense went into the costumes and the lavish set design. So I was jolted when, in the first episode—directed by Martin Scorsese no less—a showgirl shrieks, “No way!” My Partridge Dictionary of Slang says that no way first appeared in 1968.

In Mail Order Bride, a western set in 19th century Wyoming, a character says, “She couldn’t take the lifestyle.” The Oxford English Dictionary says life-style was coined in 1929. That surprised me, because I would have sworn that lifestyle didn’t show up until the 1960s.

So beware what you call an anachronism—you might get taken down a peg, as I was by the 1933 film A Man’s Castle, when Spencer Tracy says, “I’m hip to all the panhandling routines.” Really? He was “hip” back in 1933? I’d have lost that bet.

I was also put in my place by the great AMC series Mad Men when a character in the 1960s said “synchronicity,” a word that became trendy with the popular culture in the eighties. But it turns out synchronicity goes back to the fifties.

The creator of Mad Men, Matthew Weiner, was meticulous in his replication of sixties vernacular. Good for him, because a lot of watchdogs were paying close attention. I’ve read that Weiner was grilled about the show’s use of self-worth, regroup, and recon, but like synchronicity, those terms were around back then. “When in doubt,” Weiner said, “I don’t use it.”

Not all the quibbles were false alarms. Even an artist as committed as Weiner is going to slip up, as when he had someone say, “You have to be on the same page as him.” On the same page, I understand, didn’t enter the language until the late seventies.

Other Mad Men lines I had doubts about include “I’m a glass-half-full kind of girl” and “Give it a rest.” These both sound decidedly post-sixties. Why not use expressions more typical of the period, like “I’m a cockeyed optimist” and “Knock it off”? Another episode had “push back.” If your drama is set in 1965, why use a term that’s overused by politicians and pundits in 2015? If a phrase sounds too current, it risks spoiling the illusion.

And even if you could prove to me that winking goes all the way back to ancient Egypt, it still didn’t work in Cleopatra.

—Tom Stern