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The Best of Iron Man's Many Girlfriends and Lovers

List RulesVote up all of Tony's lovers you think he should've settled down with.

"Big man in a suit of armor, take that off what are you?" "Genius, billionaire, playboy, philanthropist." With emphasis on the "playboy," Tony Stark is an infamous womanizer in the Marvel comic books; it's part of his very identity. As such, he's seen a lot of women over the last 50+ years (can you believe he's been around since 1963?). We're talking about a guy who was modeled after Hugh freakin' Hefner, the founder of the Playboy empire! But which of Tony's ladies won your heart?

Who has Tony Stark dated? Who of Iron Man's girlfriends is the best? Whether you enjoy the company of blondes (Joanna Nivena), brunettes (Janet Van Dyne) or Tony's personal favorite, redheads (Natasha Romanova, Pepper Potts, Bethany Cabe, etc.) then he's the guy to talk to. 

Since there are far too many woman in the Marvel Universe that Tony's dated, we went with the best of, or at least the most noteworthy and life affecting of Tony Stark's lovers. It'd probably shorter to make a list of woman that Stark HASN'T been with in the 616 and Ultimate universes... We saw the way Aunt May was eyeballing him...

Make sure to vote up your favorite women Iron Man has dated below. 

  • 5

    Maria Hill

    Photo: Iron Man / Marvel
    In The Invincible Iron Man (Vol. 5) #10, both thinking the world is screwed, Stark and Hill have a moment of weakness. Maria wakes up in Tony's armory, abandoned, with a note that said, "Blow it up run like hell!"
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  • 6

    Madame Masque

    Photo: Iron Man / Marvel

    Tony fell deeply in love with Madame Masque despite her horrific facial scars. Because of her connection to the Maggia crime cartel and because of his reputation, the public believed Masque to be Iron Man's girlfriend and not Tony's. 

    However, the relationship ended badly when Iron Man accidentally caused the death of Madame Masque's father (whoops). She went back to a life of crime and they have remained mortal enemies since.
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  • 7

    The Wasp

    Photo: Iron Man / Marvel

    Janet Van Dyne, The Wasp, is also a founding member of the Avengers. For years, she battled crime side by side with Iron Man, never knowing his secret identity. After her divorce from Henry Pym (one of Stark's good friends and a fellow Avenger), she became involved with Tony Stark. 

    Captain America reprimanded Stark and insisted that he reveal his secret to Janet. When Iron Man removed his mask, she was very upset. She refused to pursue a relationship with one of her ex-husband's best friends. The two heroes nonetheless remained good friends.

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  • 8

    Anna Wei

    Photo: Iron Man / Marvel

    Tony Stark was trapped without his armor or his papers in one of the work camps of the Sarawak Republic. Luckily the beautiful Anna Wei intervened. To thank him for saving her son from a street gang, she offered a refuge to Stark in her own home. The two slowly learned to trust each other. She helped him recuperate his armor and he rid her of a threatening gangster. Their romance was short lived, but Anna and Tony parted good friends. He offered her a job in one of his San Francisco companies.

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