Tony Stark aka Iron Man is a genius, billionaire, playboy, and philanthropist. But when he is not developing some cutting-edge tech to save the world, he is out there scoring chicks. There are a lot of girlfriends of Iron Man that never made it to the big screen but were there in his life. While some were too stupid for anyone’s attention, some were too good… even for a guy as rich and famous as Tony Stark himself.
Tony and Natasha Romanov first met when the latter was still a Russian spy. Black Widow and her associate Boris were in a party to kill a Russian Defector, Vanko. Black Widow kept Tony distracted while Boris tried to kill Vanko. In the ensuing altercation, Vanko died but not before taking Boris with him. She would return years later as a villain and then as an Avenger herself.
Natasha Romanov aka Black Widow started out as a villain in the comic books (believe it or not). But she later redeemed herself and became an Avenger in her own right. In the Ultimates comic book universe, Natasha and Tony were closer than you could imagine. In fact, a sex tape video of Tony and Natasha was leaked via the internet. Natasha died after having betrayed the team but it was still a very painful ordeal for Tony.
Jennifer Walters was an ordinary Lawyer until she got a blood transfusion from his irradiated cousin, the Hulk. She later becomes the She-Hulk and a prominent Avenger herself. During Civil War, Walters sided with Tony. But when she realizes Tony was the one behind shooting the Hulk to Outer Space, she loses her cool and thrashes him around like a tin can.
Janet Van Dyne
Janet Van Dyne was the Original Wasp. She started out as the typical Damsel in Distress within the comic books. That was until in the 80s, she became the leader of the Avengers herself. She would later lead the team on various adventures o save the world.
Maria Hill is always seen as Fury’s second in command. But after the events of Secret War, she took in full control of SHIELD and acted as its Director. She used her position in Civil War to hunt down several rogue superhumans. Hill is highly trained in all forms of strategy and combat and has even led the Avengers one time.
Emma Frost is one of the most well known X-Men and Hellfire Club members. She is one of the most powerful telepaths on Earth. Apart from that, Emma is also capable of turning her body into an organic diamond form, thus turning her completely invulnerable to all forms of mental and physical attacks. In Civil War #3, Emma reveals she and Tony have an “arrangement”.
In the Ultimates comic book Universe, Justine Hammer is the daughter of Justin Hammer who happened to be Stark’s one of the fiercest rivals. She was gifted with superpowers thanks to the nanites in her blood but they were also weakening her body and slowly killing her. Iron Man and Justine teamed up to find a cure only to realize later on that she was working for the enemy all along.
The Starks and The Hammers have been at the forefront of a corporate cold war since decades. Justin Hammer is one of Tony’s fiercest rivals. His daughter Justine is no different either. In the Ultimates Universe, Justine actually has superpowers of her own which she threatens to use on Tony. Tony does what he does best to save himself – he sleeps with her. Now that is a way of winning your enemy’s heart.
Marianne Rodgers and Iron Man used to go out. Until it was revealed that Marianne had latent psychic and ESP abilities. But it wasn’t that that broke the relationship. Marianne was immensely emotionally vulnerable due to her powers, suffering bouts of frightening hallucinations. Tony admitted her to a mental hospital. When Marianne, who thinks Tony abandoned her, tries to kill Tony, she misses and hits a villain called Midas instead who is then rendered comatose. She is later readmitted back to the mental hospital she escaped from.
What is it with Tony and Bad girls? When Whitney Frost, Count Nefaria’s daughter, realizes her true parentage, she decides t take over her father’s terrorist organization The Maggia. Whitney becomes increasingly ruthless in her criminal schemes. When her plan for stealing precious Stark tech fails and her face gets disfigured in a plane crash, she dons a golden mask and starts calling herself Madam Masque, one of Marvel’s greatest femme fatales.
Regular movie buffs were first introduced to her character in Iron Man 3. Maya is a gifted scientist and the inventor of the Extremis Virus. In the comic, when Tony jilts her like the way he has with many other women, she decides to sell her research to A.I.M. A.I.M then uses her research to create super-powered mercenaries, Maya is being one of them. We saw in Iron Man 3 how Tony could be at two places at the same time, protecting the US President from terrorists and saving the love of his life Pepper Potts.
Gamora is easily the most badass member of the Guardians. She once described herself as ‘the deadliest woman in the Galaxy.’ Tony has a kind of fetish with the color green we guess. After dating She-Hulk, Iron Man went out with Gamora during his time as a Guardian in outer space. Safe to say neither of them was impressed by each other’s bedroom skills and Gamora soon returned to what he does best – kicking ass.
She began her comics tryst as a Hydra assassin that was made to infiltrate the Avengers. But she later became a superhero after realizing the massive fall out of her ways. One Christmas, she was caught by Tony and they kissed and it was hinted in comics that they took it to the next level.
Janet Van Dyne aka WASP or Hank Pym’s wife. But when the couple got divorced, she fell for Tony Stark. She had no idea about the fact that Tony was actually a fellow Avenger Iron Man. After being pressured by Thor and Captain America, Tony broke off the relationship.
Sunset Bain is the CEO of Baintronics, a ruthless organization engaged in illegal activities like stealing technology and selling weapons to the highest bidder. In 1999, it was revealed that Sunset Bain and Tony Stark were MIT mates where Sunset seduced Tony to extract information about his security system, she later stole this precious stark tech for a sinister purpose.
Janice Cord is the daughter of Drexel Cord, one of Starks fiercest business rivals. When Drexel activates a robot killing machine called the Demolisher to kill Stark, Janice saves Tony by giving him heads up beforehand. As a result, Drexel dies trying to kill Tony. Well, Janice and Tony decided to stay together until she is killed by Titanium Man and Crimson Dynamo.
In 1998, Tony returns from an alternate universe to find his company taken over by Kenjiro Fujikawa. His daughter Rumiko gets smitten by Tony’s charms. She enjoys a brief romantic relationship with him but eventually breaks it off. She returns to help Tony get back his company. Clarence Ward, an Iron Man impostor, kills her later.
Anna Wei was a brilliant computer hacker from the country of Sarawak. She helped Tony to find his missing tech in the third Armor Wars storyline of 2001. After Tony helps defeat some local thugs and save her son, Anna and Tony hooked up.
Bethany is a trained fighter who worked as a personal bodyguard for a host of rich clients. She was recruited by Tony to be on his side. After some time they both became a couple, as Tony further going on a downward spiral and descending into alcoholism, she helped him recover. She was last seen as the head of security of Stark Resilient, a Stark subsidiary.