The Best of Iron Man's Many Girlfriends and Lovers

Voting Rules
Vote 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. 



  • 1
    468 VOTES
    Black Widow
    Photo: Iron Man / Marvel

    Tony and Natasha Romanova dated for a short time but broke it off as soon as he found out she was a spy. (Probably with some flashbacks to his time with Sunset Bain.) She soon defected to the West, joining the Avengers. She remains one of Tony's most trusted allies. 

    In the Ultimate Universe things went even further, as seen above.
    468 votes
  • 2
    301 VOTES

    Bethany Cabe

    Bethany Cabe
    Photo: Iron Man / Marvel

    Cabe was originally hired to be Stark’s bodyguard. As she was falling in love with Tony Stark, she found herself in conflict with Iron Man (who was also supposed to be his bodyguard). She accused him of never being there when Stark really needed him. But after a while, she realized that the two men were never at the same place at the same time and figured out Stark's secret. 

    Bethany was instrumental in helping Tony in his fight against alcoholism. She became his confidant, lover, and best friend and it seemed for a time that he had finally met his perfect match. The relationship sadly came to an end when Bethany learned that her husband, Alex Von Tilburg, a man she believed to be dead, was in fact still alive in Germany.

    301 votes
  • 3
    428 VOTES

    Bourbon

    Bourbon
    Photo: Iron Man / Marvel
    I mean, we all know Stark's one true love: bourbon.
    428 votes
  • 4
    230 VOTES

    Madame Masque

    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.
    230 votes
  • 5
    315 VOTES

    Maria Hill

    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!"
    315 votes
  • 6
    295 VOTES

    Emma Frost

    Emma Frost
    Photo: Iron Man / Marvel
    During the "Civil War" storyline, while Tony was trying to recruit more members on his side, he approached the X-Men's Emma Frost, and hinted at a past relationship.
    295 votes