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

Some Democrats had privately dismissed rumors of his playboy lifestyle as unsubstantiated, according to people familiar with the conversations.

From The Wall Street Journal ● Apr. 16, 2026

But since he was a young man, he has been obsessed with creating a macho image, inventing the persona of a high-flying playboy and king of the New York real estate world.

From Salon ● Jun. 20, 2025

He has the tender, shining eyes of an ingenue while Del Campo, who has a striking birthmark on her cheek, is a femme fatale able to hold her own against Wolff’s selfish, useless playboy.

From Los Angeles Times ● May 8, 2025

Todd had always been, to Zeitoun’s mind, a bit of a wanderer, something of a playboy.

From "Zeitoun" by Dave Eggers

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

It’s a release created in SEO heaven: three of the buzziest playboys in music record a song and name it after one of the hottest genres in the world.

From Los Angeles Times ● Jul. 21, 2023

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 spent the postwar years in Paris, befriending Prince Aly Khan and other jet-setting playboys who frequented casinos.

From Washington Post ● Jan. 11, 2022

He worships the vuvv playboys he works for.

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