Iron Man has had a range of love interests, some of whom have been good for him while others have caused him harm. Madame Masque, a former enemy of Iron Man, developed feelings for him and posed as his secretary to get closer to him. Rumiko Fujikawa, the granddaughter of one of Tony’s rivals, dated Iron Man but their relationship fell apart due to stress and betrayal.

Thanks to the billionaire playboy image he projects, Iron Man has had a number of love interests. Some of the women Tony has been romantically involved with have been good for him, with his best interest at heart. Others have seriously hurt him, either physically or mentally. A few have come from the super-heroic community and others started as rivals. Here is a list of Iron Man’s top 10 love interests.

10 Kathy Dare

First Appearance: Iron Man #233

Kathy Dare is one of Iron Man’s darkest love interests. At the start, Tony and the carefree Kathy had a great time together, but it was not meant to be, and he broke it off with her. Distraught and heart-broken over the break-up, Kathy shot Tony, seemingly killing him. Instead, she temporarily paralyzed him and he went off the grid to heal. As a cover for his disappearance, Tony faked his death and Kathy, distraught over leaving Stark Industries in such a compromised position, tragically killed herself.

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9 Madame Masque

First Appearance: Tales of Supsense #97

Whitney Frost, AKA Madame Masque, is not only a love interest of Iron Man, but she is also one of his biggest enemies. The former head of the Maggia crime organization, Madame Masque came to develop feelings for Iron Man, despite being on different sides. At one point, to get closer to Tony, she posed as Krissy Longfellow, his secretary. Even after Tony found out about her deception, they continued their relationship. Unfortunately, their affair came to an end when Madame Masque’s father, Count Nefaria, returned to life, causing Whitney to resume her evil ways.

8 Rumiko Fujikawa

First Appearance: Iron Man (volume 3) #4

Rumiko Fujikawa could have been a competitor, but instead ended up dating Iron Man. The granddaughter of Kenjiro Fujikawa, one of Tony Stark’s rivals, the two began an affair shortly after Iron Man’s return following Onslaught’s attack. Rumiko’s family did not approve of her dating Tony Stark, and for a while, he believed she was only doing it to anger them. However, over time, the two developed feelings for each other, and even became business partners. Due to the stress Iron Man was facing at the time, their relationship fell apart, and she slept with one of Tony’s other rivals, but was ultimately remorseful for what she did.

7 Emma Frost

First Appearance: Uncanny X-Men #129

It is often joked that Iron Man has a thing for redheads, but he clearly has something for women with the last name “Frost” as well. The X-Men’s Emma Frost is Iron Man’s newest love interest. Tony recently became the Black King of the Hellfire Club, Emma’s former group. Posing as “average” Hazel Kendal, Emma ended up married to Tony thanks to a series of events involving Feilong, the head of Orchis. While Tony and Emma’s “marriage” is one of convenience, there is a potential for good here, as it creates a powerful alliance against Orchis and their anti-mutant agenda. Time will tell how this one will go.

6 Janet Van Dyne

First Appearance: Tales to Astonish #44

Janet Van Dyne, AKA the Wasp, helped create the Avengers alongside Iron Man, and the two had an affair after her marriage to Hank Pym collapsed. The two would date for a while, even over Captain America’s objections, but it was not meant to be. At the time, the world at large did not know Iron Man was Tony Stark, and when she found this out, broke it off with him. This sour ending did not stop them from giving it another shot many years later, after Janet’s divorce from Hank became final.

5 Hellcat

First Appearance: Miss America Magazine #2

Hellcat, AKA Patsy Walker, is another of Iron Man’s more recent love interests. The two have been friends and teammates on the Avengers for years, but when Iron Man recruited her to help him and a group of heroes defeat Korvac, the two became close, to the point where he proposed marriage to her. She turned him down, but she also convinced Iron Man to give up the Power Cosmic, which he obtained during the fight with Korvac. The affair between Hellcat and Iron Man also helped return Hellcat to a prominent place in the Marvel Universe.

4 Black Widow

First Appearance: Tales of Suspense #52

Iron Man had an affair with Black Widow not long after she first came to America. Appearing as a socialite but in actuality a Russian spy, the Black Widow wooed Tony Stark. After she was outed as an agent and returned to Russia, they broke up. Natasha would ultimately defect to America and become the Black Widow, and a hero in good standing. Black Widow would end up joining the Avengers, bringing her back into contact with Iron Man. Despite some flirtatious overtures, the two are only friends.

3 Joanna Nivena

First Appearance: Iron Man #244

Not much is known about Joanna Nivena, other than she was one of Iron Man’s first love interests. Appearing in one issue, and in a flashback at that, Joanna was once engaged to Tony Stark, and stayed with him even after he became Iron Man. Joanna was instrumental in his development as a hero, as she encouraged him to use his armor for good. However, the strain of being a hero took its toll on their relationship, and they ended it. Joanna has not been seen since, but her impact on Iron Man cannot be understated.

2 Bethany Cabe

First Appearance: Iron Man #117

One of Iron Man’s greatest love interests, Bethany Cabe has stuck by his side even after their relationship ended. Initially hired to be one of Tony’s bodyguards, the two quickly fell in love, but Bethany ended it after she discovered her first husband was still alive. The two would continue an on-again/off-again dance for a while, even after her husband re-entered the picture. While nothing ever came of it, Bethany remained a great friend and co-worker to Tony, joining subsequent incarnations of Stark Industries and serving in the Iron Legion.

Related: Iron Man Confirms He Definitely Has a Type (And at the Worst Time)

1 Pepper Potts

First Appearance: Tales of Suspense #45

Iron Man’s greatest love interest, Pepper Potts has stood by him through thick and thin. Beginning as a secretary at Stark Industries, Pepper would rise through the ranks to become a highly successful businesswoman in her own right. While the two would consummate their feelings in the MCU, in the comics they never married. Instead, she would marry Happy Hogan, one of Iron Man’s best friends. Despite their shared history and drama, the two remain good friends and Tony even gave her a suit of armor.

Iron Man has had many love interests over the years, including some not listed here. As the Iron Man mythos continues to grow and evolve, more love interests will come along.

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