Tony Stark is a playboy, not only in the Marvel Cinematic Universe, but also in Marvel Comics. He flirted with almost all pretty women and until he found Pepper Potts, he was never serious about a relationship.
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It is very difficult for someone like Iron Man to be involved in a very serious relationship because he is literally married to the superhero job. You never know what your last mission will be, so it’s best not to compromise. However, the CEO of Stark Industries has lived long enough in the comic world to be involved in many relationships.
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10 Sunset Bain
Tony didn’t hold back even during his student life. He was involved in a relationship with an older woman named Sunset Bain. There was something wrong with her and it was quite evident that she was trying to manipulate Tony. Of course, the young man wanted to impress Sunset and foolishly ended up giving the Stark Industries security code. Not long after, many prototypes were stolen and Sunset left Tony behind. A lesson learned for the young billionaire.
9 Veronica Benning
There were some dark days that Tony had to go through. He once broke his back and hired Veronica Benning as his physical therapist. During the time he was trying to re-learn to walk, he approached Veronica. The relationship became intimate but the good morning did not last long. A virus took hold of Stark and he began abusing alcohol. Not knowing that it wasn’t really Stark, Veronica became discouraged and left him.
8 Emma Frost
The Civil War story is considered one of the best of all time because of Iron Man. Fans of reading comics got to see Tony Stark’s evil side for the first time. He was recruiting superheroes to his side back then and he ran into Emma Frost.
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During his speech, Stark hinted at the relationship between them, which Emma did not deny. This was a highly unlikely reveal and although fans never got to see it, they could have guessed that Emma and Stark made a pretty decent couple.
7 Anna Wei
Tony has traveled the world in his armor and one of those times, he found himself trapped in the Republic of Sarawak doing his job of being a hero. His Iron Man suit was ripped apart and one of the locals, Anna Wei offered him a place to stay as thanks for saving his son. Eventually, they grew closer to each other, and Tony had enough time to rebuild his armor. They parted ways when it was time for Stark to leave and they did so on very good terms.
6 Justine Hammer
In a very dark story in Ultimate Comics, Tony Stark had to search for his lost technology. No wonder it was his grandfather, Howard Stark Sr., who was behind it all. And, of course, he hired Justine Hammer to keep an eye on Stark. She became close to Iron Man and they began a relationship, only for her to freak out once Tony learned the truth. Iron Man inadvertently ended up killing Howard and Justine.
5 Natasha Romanoff
Iron Man and Black Widow have been romantically involved multiple times. The first time things got intimate was when Natasha was still a spy for Russia but as soon as the truth came out, Tony had no choice but to leave her. In Ultimate Comics, however, the writers tried to explore their relationship a little further and they seemed like a very good match. It was because they were very good friends. Some would even say that Natasha seemed to like Tony more than Captain America.
4 Bethany Cabe
Bethany Cabe and Tony Stark was a very obvious relationship, once the former joined Stark’s security team. Bethany was beautiful, smart, and attractive. Tony was never going to let her pass.
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It looked like they were going to go long, but Tony’s drinking problems stopped his momentum. And things came to a standstill when Bethany learned that her husband, whom she believed was dead, was alive. There was simply no going back.
3 Maria Hill
Maria Hill and Tony Stark have worked together for quite some time and have always managed to keep things professional. But during a story where it felt like the Earth was about to end, they gave in to their wishes. They became close only for a time. It took them until morning to get back to normal and with bigger things at stake, they never had the opportunity to revisit this romantic instance.
She-Hulk has been involved in many casual relationships, the latest being the God of Thunder. It’s no surprise Jennifer Walters has also been romantically involved with Tony Stark. Their respective personalities are such that they don’t take relationships very seriously and they haven’t taken each other seriously either. But it would be a mistake to suggest that both She-Hulk and Iron Man never thought of considering each other as a life partner.
Janet Van Dyne aka The Wasp is one of the most unexpected companions Tony Stark has ever had. With the Avengers, both Iron Man and Janet have fought together, without the latter knowing the true identity of the former. When Janet divorced her husband (Tony’s good friend), she became close to Iron Man. Soon, they became involved in an intimate relationship that Captain America did not like. It was because Tony never told Janet how closely related he was to her ex-husband. As soon as she found out, it was all downhill.