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

One newspaper denounced “The Playboy of the Western World” as an “unmitigated, prolonged libel upon Irish peasant men and, worse still, upon Irish peasant girlhood.”

From The Wall Street Journal • Apr. 24, 2026

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

By the novel’s 1966 setting, Gloria Steinem had already gone undercover as a Playboy Bunny and the second-wave feminist movement was starting to gain traction in certain circles.

From Los Angeles Times • Mar. 3, 2026

Synge's landmark drama, The Playboy of the Western World, a story from the west of Ireland, which won rave reviews from London audiences.

From BBC • Aug. 9, 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