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Synonyms

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.


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

"Collins English Dictionary — Complete & Unabridged" 2012 Digital Edition © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012

Other Word Forms

Noun Inflected Forms

Etymology

Origin of playboy

First recorded in 1620–30; play + boy

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

See Examples For:

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

Before that date he was “millionaire playboy Jeffrey Epstein.”

From The Wall Street Journal Nov. 20, 2025

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

In a different sequence, our ensemble characters take turns reading an online screed caricaturing billionaires as yacht-bound playboys.

From Los Angeles Times Dec. 13, 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 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

They also need to shed any perceptions of the shoe as being for pretentious preppies, rakish playboys, or stuffy old men.

From The Wall Street Journal Aug. 31, 2016

He worships the vuvv playboys he works for.

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

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