Tony Stark aka Iron Man is known for two things – making super advanced tech and hitting on women. He is better known for the former but he is even better at the latter. With Tony being around in Marvel Comics as long as anyone can possibly remember, the list of Tony’s ex-flames is long and wide.
Gamora is the key member of Guardians of the Galaxy and definitely one of the most badass female superheroes in the Marvel comic book universe. She once described herself as ‘the deadliest woman in the Galaxy.’ Tony has a kind of fetish with the color green due to things happened to him in the past. After dating She-Hulk, Iron Man went out with Gamora during his time as a Guardian in outer space. Well, they were doomed, to begin with, and obviously, neither of them was impressed by each other’s bedroom skills and Gamora soon returned to what she does best – ass-kicking.
When Tony became a member of the Guardians of the Galaxy in 2013, he realized he was attracted to the most dangerous woman in the Galaxy. They hit it off soon after but the eventual experience was bad, for either of them,
Spider-Woman started out as a Hydra assassin that was made to infiltrate the Avengers. But she later became a superhero after realizing the error of her ways. One Christmas, she was caught by Tony under the Christmas mistletoe. They kissed and it was heavily suggested they took it way beyond than just that.
Maria Hill is always seen as Fury’s second in command. In the movie ‘The Avengers’ she was the one in-charge of ground operations and she is good at her job. But after the events of Secret War, she took in full control of SHIELD and promoted to the position of Director. She used her position in Civil War to hunt down several rogue superpowered people. She is a highly trained soldier in all forms of combat and strategy and has even led the Avengers one time.
She was later replaced by Iron Man under orders from the President. When Tony was also on the run, Hill and he teamed up for a mission and the result was as you see in the picture.
Janet Van Dyne is better known as Ant-Man aka Hank Pym’s wife. But one time, when the couple was divorced, she fell for Tony Stark. Janet didn’t know 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 corporate organization involved in stealing technology and selling weapons to the highest bidder. In 1999, it was revealed that Sunset Bain and Tony Stark were MIT colleagues where Sunset seduced Tony to learn about his security system, only to steal precious stark tech later.
In the Ultimates Universe, Justine Hammer is the daughter of Justin Hammer, Stark’s fiercest rival. She was gifted superpowers thanks to the nanites in her blood but it was also killing her. Iron Man and Justine teamed up to find a cure only to realize that she was working for the enemy all along.
The Starks and The Hammers have always been at the forefront of a corporate cold war since many years. Justin Hammer is one of Tony’s dangerous and fiercest rivals. His daughter Justine is no different. In the Ultimates Universe, Justine actually possesses superpowers of her own which she threatens to use them on Tony. What do you think happened next? Well, Tony does what he does best to save himself – he sleeps with her. Now that is a way of winning your enemy’s heart.
Janice Cord is the daughter of Drexel Cord, one of Starks most dangerous business rivals. When Drexel activates a robot killing machine called the Demolisher to kill Stark, Janice saves Tony by warning him beforehand. Drexel dies trying to kill Tony. Janice and Tony 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 soon falls for Tony. She enjoys a steady relationship with him but eventually breaks it off. She returns later 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 hurting her son, Anna and Tony become a couple.
Bethany is a trained fighter who worked as a personal bodyguard for Wealthy clients. She was soon hired by Tony to be his. After they both became a couple, Tony descended into alcoholism but she helped him recover. The last time we see Cabe was as the head of security of Stark Resilient, a Stark subsidiary.
Madam Masque is the daughter of Count Nefaria, the erstwhile leader of the criminal organization The Maggia. Masque was forced to be ruthless so that she is not seen as weak by her criminal counterparts. But there was still hope for her. Tony realized there was still a noble spirit deep within Madam Masque.
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.
She has been known to use skimpy outfits and her own sexuality to level the playing field. Iron Man and Emma Frost, as she says, have an “arrangement.” Superhuman friends with benefits!!! Count us in, please.
Jennifer Walters loves being She-Hulk. She loves being with men even more. Iron Man and She-Hulk are completely perfect for each other – both are distant and not looking for a long-term relationship. Too bad it didn’t work out.
Tony Stark aka Iron Man and Natasha Romanov aka Black Widow first met when the latter was still a Russian spy. Once she and her associate Boris were in a party to kill a Russian Defector named Vanko. Black Widow kept Tony distracted with her charms while Boris tried to kill Vanko. In the ensuing altercation, Vanko died but not before taking down Boris with him. She would return years later as a villain and then as an Avenger herself.
Natasha Romanov started out as a villain in the comic books. She later became an Avenger in her own right. In the Ultimates universe, Natasha and Tony were closer than you could imagine. A sex tape video of Tony and Natasha was leaked via the internet. Natasha was dead, having betrayed the team. But it was still a painful ordeal for Tony.
The MCU movies popularized the Stark-Potts relationship angle. But the comics have been portraying their on again off again relationship for a very long time. Pepper Potts first appeared in 1963. She was Tony Stark’s secretary who immediately fell for him. Stark ignored her and she later married Happy Hogan, Stark’s bodyguard. After Taskmaster kills Happy Hogan, Tony rehires Pepper who later becomes the CEO of his company. Of all the women that have come and gone, it has always been Pepper who has stayed by Tony’s side.
In the MCU, she has last seen in Spider-man: Homecomingwhereinn the second last scene Tony announced his engagement to her to a room full of people and press. The latest gossip from the sets of Avengers 4 is that she was seen next to Robert Downey Jr. (Iron Man), Mark Ruffalo (The Hulk), Jon Favreau (Happy Hogan) and Anthony Russo and she might have a guest appearance in the movie as there are no plans for Iron Man 4.