play·​boy ˈplā-ˌbȯi How to pronounce playboy (audio)
: a man who lives a life devoted chiefly to the pursuit of pleasure

Examples of playboy in a Sentence

She was dating a rich American playboy who was seeing two other women at the same time.
Recent Examples on the Web Or Jimmy Kimmel, another pal, who never misses the opportunity to paint me as the ultimate playboy. Dory Jackson, Peoplemag, 21 Oct. 2023 Although Kelce has no doubt matured a bit since that playboy experiment, Catching Kelce is still the best resource for Swifties looking to learn what Taylor is in for as the two explore a dating situation. Miles Klee, Rolling Stone, 26 Sep. 2023 Buss, the flagrantly promiscuous playboy, peruses his scrapbook of romantic conquests at the end of the season premiere before he is frozen in nostalgia at a photo of Honey. Keith Nelson, Men's Health, 15 Aug. 2023 Caine has played secret agents, playboys, adventurers, schoolteachers and killers. Amarachi Orie, CNN, 14 Oct. 2023 Readers first met Ripley in 1955, when Highsmith introduced him as a young American of indeterminate desires whose envy of the rich, indolent playboy he’s been hired to bring home from Italy shades into a kind of lethal longing — to be him, have him, replace him. Mark Harris, New York Times, 17 Aug. 2023 The book rotates perspectives, with chapters devoted to everyone from a renowned Palestinian baker and his son, to a journalist and an American playboy who’s just joined the Israel Defense Forces (IDF). Seth Combs, San Diego Union-Tribune, 30 July 2023 Far from accompanying the Red Army during its battles against the fascist invaders, the correspondents instead spent almost all of their time confined to Moscow’s Metropol Hotel, a czarist-era hot spot for playboys’ galas and trysts that became a wartime gilded cage. Paul Musgrave, Washington Post, 3 July 2023 Despite his position, Edward VII had developed a reputation as a playboy and a contentious relationship with his parents; Victoria blamed him for the death of his father in 1861, largely preventing him from having political position or influence until the end of her life. Lauren Hubbard, Town & Country, 26 Mar. 2023 See More

These examples are programmatically compiled from various online sources to illustrate current usage of the word 'playboy.' Any opinions expressed in the examples do not represent those of Merriam-Webster or its editors. Send us feedback about these examples.

Word History

First Known Use

1829, in the meaning defined above

Time Traveler
The first known use of playboy was in 1829

Dictionary Entries Near playboy

Cite this Entry

“Playboy.” Dictionary, Merriam-Webster, Accessed 9 Dec. 2023.

Kids Definition


play·​boy -ˌbȯi How to pronounce playboy (audio)
: a man whose chief interest is the pursuit of pleasure

More from Merriam-Webster on playboy

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