Pretty please (with sugar on top)

Whipped cream works wonders with our cats, by the way.

Dear Word Detective: You know how hard it is to get a cat to do anything it doesn’t want to. So this morning I asked my cat to get off my robe and I actually said “pretty please,” and then, just to increase my humiliation, added “with tuna on top” (hey — she’s a cat). Where the heck did the phrase “pretty please” come from, and when and why did we feel the need to start adding sugar on top? — Jackie.

Ah, cats. Lovely pets, I hear. Someday I hope to have one or two. Oh those? Those aren’t cats. Those are demons from another dimension sent to rob me of my sanity by destroying the furniture and smashing every bit of crockery in the house, and then lying peacefully amidst the wreckage as if to say, “Don’t look at us, we’re just little cats, it must have been that idiot dog again.” It’s all a lie, of course. I once watched an eight-week old kitten throw a ten-pound dictionary across the room.

“Pretty please” is a phrase used, as the Oxford English Dictionary notes,”in emphatically polite or imploring request[s].” “Pretty please with sugar on top” is Extra Strength Pretty Please, deployed by children and desperate adults in an appeal for cooperation when all other entreaties have failed.

Plain old “please” used in requests (“Please send money”) is an adverb, based on the verb “to please” meaning “to be agreeable or pleasant,” derived from the Latin “placere” (“to be pleasant”). The “request” use of “please” probably originated as a shortened form of the phrase “if it pleases you [to do whatever].”

“Pretty” primarily means, of course, “attractive,” and is rooted in the Old English “praettig,” which meant “clever.” In the 16th century, “pretty” came into use as an adverb meaning “to a considerable extent” (“Bob’s pretty sick”) or, as an adjective, “substantial” (“That boat must have cost a pretty penny”). In the phrase “pretty please,” “pretty” functions as an intensifier, ratcheting up the strength of the “please” to signify that the speaker really, really wants whatever it is they’re asking for. “With sugar on top” turns the urgency dial up to eleven.

The earliest citation in the Oxford English Dictionary for “pretty please” is from 1913, and the earliest for “pretty please with sugar on top” is from 1973. But my guess is that “with sugar on top” actually arose much earlier, at least by the 1950s. While sprinkling sugar on food has a long history, it was in the 1950s when ready-made sugar-coated breakfast cereal became popular, and the phrase may have been spawned then in imitation of advertising (“Ask Mom for Choco-Balls — the ones with with sugar on top!”) for such wholesome fare.

“Pretty please with sugar on top” was always a bit excessive coming from a child, and on the lips of an adult is often meant as sarcasm, as in Quentin Tarantino’s film Pulp Fiction, where a character says, “I need you guys to act fast if you want to get out of this. So pretty please, with sugar on top, clean the [bleeping] car.”

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