Synonyms

playboy

American

[pley-boi] / ˈpleɪˌbɔɪ /

noun

a man who pursues a life of pleasure without responsibility or attachments, especially one who is of comfortable means.

playboy British

/ ˈpleɪˌbɔɪ /

noun

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

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.

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

Jarvis, the fictional AI from Marvel, was once known for helping billionaire playboy turned superhero Tony Stark save the world.

From The Wall Street Journal • Nov. 14, 2025

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

It is about a con-man taking on the identity of a wealthy playboy.

From BBC • Aug. 8, 2025

You’re a failure, a playboy, a racetrack tout.”

From "A Confederacy of Dunces" by John Kennedy Toole

Definitions and idiom definitions from Dictionary.com Unabridged, based on the Random House Unabridged Dictionary, © Random House, Inc. 2023