9. Madame Masque Whitney Frost
Madame Masque or "Big M" as she was first known in Iron Man's early days to most of the men in her life, namely servitor lackeys in the employ of the Maggia, Marvel Comics' version of the Mafia. Madame Masque is everything you'd expect of a psychotic and ruthless crime-maven hardened by years of controlling an international syndicate of criminal enterprise. Years of working with or against criminals like Count Nefaria, Norman Osborne or The Hood have given Madame Masque a sense of cold-bloodedness and a canny instinct for survival. Her years of exposure to these ruthless villains coupled with her weapons and combat training mean that a valentine from this woman will either be some sort of hi-tech explosive ... or a decapitated horse's head in your bed.