Throughout the years, Tony Stark has acquired the reputation of a playboy and a real casanova. But although his lady friends have indeed been numerous and his relationships relatively short;
Meredith McCall became Stark's first love when they were still teenagers. Since both their fathers were business rivals, they separated the young couple by sending them to two separate colleges. Years later, Iron Man saved Meredith's life after she had been kidnapped by the Controller. When he learned that she was now married, Stark decided that it was better to not renew their relationship.
Sunset Bain; met Tony Stark while he was still a student at M.I.T.. A simple flirt quickly turned to passionate love. Following Sunset's suggestion, Tony accepted to keep the relationship secret from his parents, supposedly because Sunset was slightly older than him. She was only five years older, but Stark was still very naive in those days and Baine did not hesitate to use this to her advantage. She managed to convince him to reveal to her the security codes to his father's company. He accepted in order to impress her. Soon afterwards, masked men attacked Stark Industries and stole half a dozen prototypes. Sunset then dumped Tony very suddenly and less than a year later, thanks to new prototypes that were strangely familiar to the ones that had been stolen, she founded her own company; Baintronics, Inc..
Joanna Nivena was Stark's fiancee when he had his accident in Vietnam. When he got back to the States, Stark had to wear his metal chestplate at all times in order to stay alive. Convinced that he could not be a good husband for Joanna in this state, he ended the relationship without offering any kind of explanation.
Cynthia was one of the many dates Stark had to forget Pepper Potts, even though he mistook her for Sandra.
When Tony Stark was captured by the Melter, she and several other of Stark's dates rushed to the Stark Enterprises Main Plant to check if Tony was still alive.
Nan was one of the many dates Stark had to forget Pepper Potts, even though he could only see her once a month.
Pepper Potts became Tony's personal secretary, the two of them fell secretly in love with each other. But Stark remained distant and cold. He was convinced that the cold metal chestplate he was forced to wear day and night, hidden under his clothes, made all romance impossible. Pepper ended up marrying Stark's chauffeur, Happy Hogan. After many years, the marriage ended in divorce. Pepper was again hired by Stark and love seemed to once more resurface for a time. But after a passionate kiss, Pepper and Tony concluded that their mutual attraction was a thing of the past and that a solid friendship would suit them better. For years, Pepper was one of the very few people who knew Tony was Iron Man.
Natasha Romanoff aka the Black Widow dated Stark for a short time after she arrived in the United States, but the relation ended abruptly when Tony learned that the beautiful Russian was in fact a Soviet spy. Later, she defected to the West and joined S.H.I.E.L.D. and then the Avengers and became one of Stark's most trustworthy allies.
Janice Cord was the daughter of Drexel Cord, one of Stark's business rivals. The father demanded that his daughter ended the relationship with his young competitor. When her father died, she became Tony's girlfriend. But the relationship ended tragically. She was seriously injured during a battle that opposed Iron Man to his two worst enemies of the time Titanium Man and Crimson Dynamo. She died in Iron Man's arms, unaware that he was the man she loved.
Marianne Rodgers is one of the strangest women that Stark ever met. Gifted with powerful psychic abilities that she is completely unable to control, she said she could see the future and believed that she would one day be the cause of Iron Man's death. Her powers eventually drove her mad and she ended up in an asylum.
Whitney Frost aka Madame Masque began a relationship with Tony despite the horrible scars that had disfigured her a few years before. Because of her connections to the Maggia crime cartel, and because Stark wished to preserve his reputation, the general public believed Masque to be Iron Man's lover, not Stark's. The relationship came to an end when Iron Man accidentally caused the death of Frost's father, the terrible count Nefaria. Whitney returned to her life of crime and became one of Stark's worst enemies. Visit the section about Iron Man's foes to learn more about Madame Masque and her father.
Bethany Cabe was hired by Stark to be his bodyguard. As Bethany was falling in love with Tony, she found herself in conflict with Iron Man. She accused him of never being there when Stark really needed him. But after a while, she realized that the two men were never at the same place together and she figured out Bethany's secret. Bethany was instrumental in helping Tony in his fight against alcoholism. She became his confidant, lover and best friend and it seemed for a time that he had finally met his perfect match. The relationship sadly came to an end when Bethany learned that her husband, Alex Von Tilburg, a man she believed to be dead, was in fact still alive in Germany.
Janet van Dyne aka the Avenger; Wasp after her divorce from Hank Pym became involved with Tony Stark. Captain America reprimanded Stark and insisted that he revealed his secret to Janet. When Iron Man removed his mask, she was very upset. She refused to pursue a relationship with one of her ex-husband's best friends. The two heroes nonetheless remained good friends. They eventually managed to rekindle their romance.
Indries Moomji dated Tony during a very vulnerable moment in his life. What he did not know is that she had been hired by Obadiah Stane, who used her in his plot to destroy Tony and take control of Stark Industries. Following orders, she manipulated him into falling in love with her, and then rejected him coldly. Heartbroken, Stark sought relief in alcohol.
Heather Glenn was one of the worst people he could of dated herself an alcoholic, the two dragged each other even deeper in alcohol abuse. Stark soon found himself completely homeless, de-possessed, and unable to access his fortune. Heather met her end most dramatically; she committed suicide.
Kathy Dare began dating Tony with the agreement that they were not exclusive. She agreed but began to be jealous and and possessive. Tony ended the relationship and Kathy in a mad rage, shot him. The bullet crippled him and Kathy who was oversome with guilt killed herself.
Dr. Su Yin was one the of the best neurologists in the world. She was hired to help Tony overcome his spine injury. The two fell in love but Su Yin revealed she was married and wanted to remain faithful to her husband.
Veronica Benning was brought in a his personal physiotherapist.She helped him walk again and the two became very close. However the computer virus VOR/TEX took control of his body and became very drunk, he was so rude to her she left never to return.
Rumiko Fujikawa first met Tony when her company Fujikawa, to become the Stark-Fujikawa conglomerate after taking over his company . She dated Tony to get back at her father. However the relationship was rocky from the start. The relationship ended after he caught her in bed with his rival Tiberius Stone.
Calista Hancock's relationship with Tony began when he gave up his fortune and worked under the alias Hogan Potts. She hired him to work at her company Askew Electronics. The company was attacked and she was forced to declares bankruptcy. However she later found out he was really Tony Stark and broke up with him never to be seen again.
Anna Wei first encountered Tony when he was injured in Sarawak. She saved his life and helped him recuperate and when he was well he helped her deal with a group of threatening gangster. Their romance was short lived, but Anna and Tony parted good friends. He offered her a job in one of his San Francisco companies. 
- ↑ Iron Man #28
- ↑ Iron Man Annual #11
- ↑ Iron Man #244
- ↑ 4.0 4.1 4.2 Tales of Suspense #89
- ↑ Tales of Suspense #90
- ↑ Tales of Suspense #45
- ↑ Tales of Suspense #52
- ↑ Iron Man #12
- ↑ Iron Man #36
- ↑ Tales of Suspense #98
- ↑ Iron Man #117
- ↑ Avengers #224
- ↑ Tony Stark: Iron Man #4
- ↑ Iron Man #163
- ↑ Iron Man # 171
- ↑ Iron Man #222
- ↑ Iron Man #223
- ↑ Iron Man #233
- ↑ Iron Man #270
- ↑ Iron Man #292
- ↑ Iron Man Vol 3 #4
- ↑ Iron Man Vol 3 #42
- ↑ Iron Man Annual #2001