playboy

American  

[pley-boi] / ˈpleɪˌbɔɪ /

noun

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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Etymology

Origin of playboy

First recorded in 1620–30; play + boy

Example Sentences

As for her own mindset, Wilkinson has moved on from her Playboy days and is committed to her work in real estate so that others will do the same.

From MarketWatch • Apr. 3, 2026

Playboy and the New Yorker rejected his early cartoon offerings, but United Media gave him a contract for newspaper syndication.

From The Wall Street Journal • Jan. 13, 2026

Ben Kohn, CEO of Playboy, described California as being “anti-business,” saying the state is an “extremely expensive place” to operate.

From Los Angeles Times • Aug. 15, 2025

Brian Karem is the former senior White House correspondent for Playboy.

From Salon • Jun. 26, 2025

He called himself Shelley the Playboy, and speaking in code on the radio, he kept us abreast of the plans to march.

From "While the World Watched: A Birmingham Bombing Survivor Comes of Age during the Civil Rights Movement" by Carolyn Maull McKinstry