Oh, Batman, you rogue
You may know Batman as a dark vigilante or a goofy TV character, but you probably don't think of him as a skirt-chasing scoundrel. In Batman #153, dated February 1963, the Caped Crusader showed off his bad behavior.
While stranded on a strange world with his editorially mandated proof of heterosexuality, Batwoman, Bruce Wayne said sweet words when the pair were in dire straits.
Where was the worst of Batman's behavior? That came once the Bat-couple emerged from danger.