Alan Mays' photos with the keyword: winking

In this Halloween postcard dated 1908, a couple of black cats are looking up at a girl and boy who are leaning over a winking jack-o'-lantern. Handwritten message on the other side of the postcard, which was postmarked in Nelson, N.Y., on October 30. 1912: "10/30/12. Dear Nephew, Have you gathered many nuts this fall? Best wishes for a Happy Halloween. With love from Aunt Cora."

Here's a wireless telegram That I will send to you I'm in love with you—I am I love you 'deed I do Be my valentine. R. F. Outcault Cartoonist Richard F. Outcault (1863-1928) featured Buster Brown and his dog Tige—both of them winking and smiling—in this valentine from 1904.

"To my valentine. I'm a socialist, will you be one? Free drinks, free money, free love. Ellam." Postmarked Saginaw West Side, Mich., Feb. 4, 1911, and addressed to Ward Brown, 820 North Mason, Saginaw West Side. Handwritten message: "I hope you are as I am and don't forget that day. You know and I know, and why should we forget it." Artist-signed postcard by William Ellam.