playboy

American  

[pley-boi] / ˈpleɪˌbɔɪ /

noun

• playboys
  plural

1. a man who pursues a life of pleasure without responsibility or attachments, especially one who is of comfortable means.

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playboy British  

/ ˈpleɪˌbɔɪ /

noun

1. a man, esp one of private means, who devotes himself to the pleasures of nightclubs, expensive holiday resorts, female company, etc

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Other Word Forms

Noun Inflected Forms

• playboys
  plural

Etymology

Origin of playboy

First recorded in 1620–30; play + boy

Example Sentences

See Examples For:

playboy playboys

The 41-year-old royal misfit has long struggled with the monarchy's strictures, shaking off the angry young man and "playboy prince" tags only to find himself at loggerheads with his closest relatives.

From Barron's ● Aug. 23, 2026

Ernst returns to Tokyo, now fronting as a playboy plutocrat to mask his espionage.

From The Wall Street Journal ● Jun. 26, 2026

"As far as everybody's concerned, you're a playboy," she told him, accusing him of "parading" his relationships with people including British supermodel Naomi Campbell.

From BBC ● Feb. 24, 2026

Five years later, she enthralls Majnoo, the playboy son of billionaire parents, and the pair go on to have a spectacular wedding.

From Los Angeles Times ● Nov. 4, 2025

You’re a failure, a playboy, a racetrack tout.”

From "A Confederacy of Dunces" by John Kennedy Toole

Paul was “one of the most gregarious playboys in New York City,” according to biographer Frank Brady, author of “The Publisher,” and Paul and William Randolph Hearst were regulars at New York nightclubs.

From The Wall Street Journal ● Apr. 5, 2026

One wonders what he really thought about the pampered, preening, multimillionaire playboys of the contemporary global game, who change hairstyles weekly and win world championships sparingly.

From Los Angeles Times ● Dec. 29, 2022

Until his social media ban, Tate was operating something called Hustler University, which promised, for $49 a month, to turn his audience into rich playboys, as he presents himself to be.

From Salon ● Aug. 23, 2022

He reserves some of his greatest ire for FBI Director J. Edgar Hoover, who criticized the early CIA as a refuge of irresponsible adventurers, Ivy League playboys and communist sympathizers.

From Washington Post ● Oct. 8, 2020

He worships the vuvv playboys he works for.

From "Landscape with Invisible Hand" by M.T. Anderson