In the MCU, Tony Stark, aka Iron Man, really only had eyes for Pepper Potts, even if he did have a fling with Christine Everhart in the first film and he showed interest in Natasha Romanoff in Iron Man 2. That’s not the case in the comics, where Stark has accumulated something of a rolodex of previous romantic conquests. From fellow superheroes to enigmatic hedonists, he’s been with them all. And like with any long list of individuals, some are better than others, in terms of whether they were good for Stark or, in a more general sense, just how good they were as human beings.
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What follows are the worst and the best of his relationships. Some who have tried to take his life and some who, thanks to his tendency to devolve into substance abuse without someone to keep his mind right, have saved it.
5) Kathy Dare
First appearing in Iron Man #233, Kathleen ‘Kathy’ Dare was Tony Stark’s equal in that she was something of a hedonist. Unfortunately, she was also a psychopath, with at least two kills under her belt. One was her own brother when they were children and another was a musician she stalked.
Like with the musician, Dare begins to stalk Stark once their relationship has soured and, ultimately, she shoots him. With Col. James Rhodes’ help, Stark’s death is faked, and a funeral is held.
4) Indries Moomji
Debuting all the way back in 1982’s Iron Man #163, Indries Moomji, aka Queen, was a lover who was too good to be true. Considered one of the most beautiful women on the planet, it’s no wonder she caught Stark’s eye, but her intentions with him are far from noble.
She’s actually a pawn of Obadiah Stain, and when she and Stark meet at a disaster the latter is trying to prevent, her being a bystander is no accident. She plays with his mind by tempting then rejecting him, all the while convincing him to drink more and more until he eventually falls so far off the wagon he must hand the reins of his company to Stane.
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3) Black Widow
Like how Captain America and Black Widow made for a great duo in the MCU, Stark and Black Widow were a duo in the comics. Just in a more romantic sense.
Depending on which line of comics you read, their relationship has varied. Sometimes they’re just allies, like in the movies, sometimes they have a fling, and in one case she initiated a romance with Stark so she could steal information from Stark Industries. Regardless, their relationships never last long, and in storylines where she doesn’t get killed, they typically end up just being friends.
2) Pepper Potts
From their budding romance and flirtation in the original film to their sharing Tony’s final moments in Avengers: Endgame, Stark and Virginia ‘Pepper’ Potts went through quite a bit in the MCU. The same is true for the comics.
Potts has been a stable character in Marvel comics for decades, dating all the way back to the ’60s. Throughout her first string of issues, she was actually in the middle of a love triangle between Stark and Happy Hogan. In fact, she’s been with Hogan in the various comic lines as much as she’s been with Stark, if not more so.
1) Emma Frost
When Stark took off the armor and put on a suit for his wedding, it wasn’t so much due to his love for mutant Emma Frost as much as it was for a specific noble purpose. Like other members of her group, she was being hounded by anti-mutant organization Orchis, and the wedding was a way for her to be in the public eye without being targeted.
It’s an interesting relationship because, while the marriage was something of a sham, it was still clear the two had a certain level of affection for one another. Even after the marriage was annulled, the two showed respect and compassion for one another. It was enough to make one wish they had given a life together a try for real.
