Valentine’s Day, the Vintage Playboy Way

Twelve cartoons from the archives that are bound to make you blush, or laugh (or both).

Entertainment & Culture • February 14, 2026

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Written by PLAYBOY EDITORIAL

Valentine’s Day is for lovers, and in this case it’s for lovers of a good laugh. The romance holiday has always been a big one for Playboy, featuring steamy pictorials, full-book reflections on attraction and desire, and, of course, cartoons. From the droll to the skeptical to the downright quirky, these cartoons capture the silly side of not just love and sex, but the holiday itself.

Enjoy a few funnies from Playboy‘s archives to celebrate this Valentine’s Day.

“There they are again!” *Michael Folks, 1971*

“To my valentine, Brad, with all my love, Betty.” *Rick Stromoski, 1994*

“Safe sex, you know.” *Peter Kohlsaat, 1994*

“For us it was a case of love at first sighting.” *Glenn McCoy, 1996*

“This is our latest. A combination love-and-hate potion. *Very* sophisticated.” *Ed Fisher, 1996*

“Look, kid, from now on just shoot your arrows – then bug out!” *Art Krusz, 1966*

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Valentine’s Day, the Vintage Playboy Way

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