Mickey and Minnie Mouse flirt in "Puppy Love" (1933)
Betty Boop loses her top while Bimbo loses his heart in “Any Rags” (1932) - Max Fleischer
A Pre-code cartoon - after the Hays Code went into effect in 1934, Betty’s image changed and the Fleischer Brothers were forced to depict her in skirts below the knees and as a much more demure character.
Harold and a pretty girl flirt with elbows in “Hey There” (1918)
A gentleman caller flirts with the maid whose taken his hat - “Girl Shy” (1924)