Pretty Please and Similar Phrases

I was wondering who uses 'pretty please?' Is it used mainly by girls? Under what circumstances? Thank you for replying.

This is, I think, an instance of ‘baby-talk’ (what linguists call child-directed speech), which is a special dialect adopted by adults in speaking to small children. Although medica is undoubtedly correct in asserting that children employ such terms as “pretty please”, “boo-boo”, “yucky” with each other, I believe they learn them in the first instance from adults.

Some elements of baby-talk—simplified syntax, a deliberately narrowed lexicon, morphological adjustments to mark word and phrase boundaries more clearly—are believed to be of value in providing a child more intelligible models for imitation. But there is a large range of ‘styles’ within this dialect, and many people adopt distinctive (mis)pronunciations and words and phrases which they suppose are characteristic of child speech, as if the child's progressive acquisition of language were not an awe-inspiring and heroic achievement but a species of imbecility to be catered to. At one time it was common in novels to represent the speech of children as baby talk—very like the demeaning representations of African-American or rural or foreign speech which once passed for humor on the stage and in literature.

Baby-talk is also used to pets, and with markedly ironic intent in ordinary speech between adults. And some children, having found that baby talk is regarded as ‘cute’ and endearing, carry some of it terms into adolescence and even adulthood. My impression is that this is less common than it was fifty years ago; I hope I am right.

"Pretty" is generally prepended to "Please" as an intensifier, in much the same way that one might use "really" before an adjective. You could double down on this intention by appending "with sugar on top" to the end as well.

The phrase is primarily used by children, or those speaking to them, or seeking to sound 'childlike' in their usage, rather than by girls; while there may be some gender disparity in its usage, the difference is negligible compared to the overwhelming shift in frequency of use between children and adults.

Children are taught to be polite - to say the magic word "please". But what if "please" does not work? A new "magic word" is needed. So one progresses to "pretty please". And if that does not work, one progresses to "pretty please with sugar on top". Basically, one has graduated from politeness to persistent begging. This tactic might work best for a pretty girl with a pretty smile; and men and boys might consider it beneath their masculine dignity - but I leave that to your individual judgment.

From the song: "Don't pull your love":

If I threw away my pride

And I got down on my knees

Would you make me beg you, "pretty please?"