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

LONDON—In 2001, Prince Andrew retired from active duty in the Royal Navy, with a reputation as a war hero and something of a playboy.

From The Wall Street Journal • Feb. 21, 2026

Oh yeah, and in 1992 Donald Trump was a playboy tycoon in his mid-40s, at the peak of his tabloid celebrity.

From Salon • Aug. 31, 2025

Not only did its first installments change directors and tones, they even radically changed Hunt’s personality from a loudmouth to a playboy to a devoted husband.

From Los Angeles Times • May 16, 2025

By the encore, he'd given up all pretence of being a high-rolling playboy.

From BBC • Mar. 30, 2025

He had a bevy of female admirers — but also a coterie of critics, who considered him a dandy and a playboy.

From "Long Walk to Freedom" by Nelson Mandela