Tony Stark is one of the more polarizing characters in comics. You either love him or hate him, and it's easy to see why. Dogmatism mixed with rich boy flippancy isn't always the best look. On the other hand, he's been with the Avengers pretty much since day one, he's invented half the tech in the Marvel Universe, and at least he's got a good sense of humor about himself.
At first glance, I always thought Tony was a little shallow, but upon a closer look this guy has been through the ringer. He might have had a lot of loves in life, but most of them utterly crushed his already-overburdened heart into pulp—not to mention most of them have been supervillains.
Most fans will recognize his relationship with Pepper Potts from the Iron Man and Avengers movies, but in the comics their attraction was more of an on-and-off thing that lasted decades and caused a lot of problems between her and her husband, Happy Hogan. The comics version of Pepper ultimately divorces Happy, and she and Tony usually leave things off by agreeing to just be friends. That typically leaves us with one very single, very available multimillionaire with an inferiority complex running around the Marvel universe most of the time. Besides a fling with the She-Hulk and his short-lived dalliance with a then-villainous Black Widow, here are some other women to show up on Tony's dance card.
It's not really Sunset Bain's fault she's a supervillain. Naming your kid Sunset Bain is like naming your kid Jarvis; you already kind of have a future planned out for them. A fellow undergraduate at MIT, Sunset Bain pretty much dated Tony Stark just so she could steal his inventions and break his heart. Admirable!
Although she first showed up in comics as a Machine Man villain, Bain has gone on to cause all kinds of problems for heroes across the Marvel universe, and that's the kind of ambition I really admire in life. Despite being a fairly awful human being, Sunset's saving grace is that she's brilliant and really good at tricking everyone—all the time! Seldom does anyone get the drop on her, and she's not above seducing random supervillains who she can easily control to further her own ambitions.
Occasionally going out as a supervillain herself, Sunset's incredible given name is equaled only by her villain identity: MADAME MENACE. I understand that Sunset Bain is supposed to be kind of the worst, but I think she's great. I'm also made slightly uncomfortable by the full acknowledgment that Sunset Bain could easily manipulate me into stealing top-secret technology from Stark Industries, but at least I know that about myself now—and it helps me understand Tony Stark a little better.
Janet Van Dyne
Out of everyone on this list, Janet is my favorite. Not just favorite of Tony's girlfriends, but favorite everything. Favorite Avenger, favorite character with shrinking powers, favorite bobbed haircut in comics, you name it. Janet Van Dyne has many strange loves of her own, having initially shown up as a debutante with a crush on Ant-Man that turned rapidly to marriage and then divorce.
After Janet booted Hank Pym from their house for the first of many times, her fellow Avenger Iron Man noticed that his own sympathy for her seemed to be rooted in something deeper than platonic concern. The two of them began dating, and they were an easy match given their mutual love of socializing and travel. The problem was that Tony had just recently “come out” as Iron Man and he kept that information from Janet, fearing it would lead her to break things off with him. As usual, the facade didn't exactly help his case and when she found out, Janet tearfully asked him to leave.
Tony was quietly heartbroken, while Janet immediately got over it by focusing on her work. I'm of two minds about their relationship. One's convinced that these two deserve another chance. Then again, one of the reasons I love Janet Van Dyne ever so dearly is that she showed Tony the door at the slightest hint of BS.
I have a special affinity for psychics in genre. I share many qualities with them, including their tendency to constantly point out the obvious as well as their knack for falling over unconscious when they suddenly have too many feelings. Thus did I love Marianne Rodgers, a woman who showed up more or less to say ominous things about Tony Stark's death.
They were even engaged at one point because, honestly, who hasn't been engaged to Tony Stark? Marianne ultimately broke it off because she was convinced he'd die if they stayed together, but she later came to believe that looking at Tony Stark's soul had driven her to madness. Relatable. Tony broke up with her and had her committed, which probably didn't help their dynamic much because, you guessed it, Marianne returned as a supervillain. TONY! You do these things to yourself!
Unfortunately, Marianne was never a hugely important character, but she did contribute to the Marvel universe by telling Iron Man, “hey, your gray metal monster suit is kind of freaking people out, maybe you should pay someone to redesign that thing for you before you traumatize an entire generation of children.” Thanks, Marianne!
Do you ever read a comic and just think to yourself, "Wow, it really seems like this writer was going through some stuff when they wrote this?" That's kind of what it's like to read the issues featuring Kathy Dare, AKA The Woman Who Shot Iron Man. Kathy just kind of shows up in Iron Man #234 and presumes herself right into a relationship with Tony Stark, who is 1) already dating someone, and 2) a complete fool.
A certain James Rhodes fulfills his lasting destiny of always being much smarter than Tony Stark and gently chastises him for seeing too much of Kathy, at which time Kathy attempts to influence Tony into breaking up with his friend. That obviously doesn't work, but it does lead to both Tony and Rhodey making some pretty uncomfortable physical threats towards her in the following issues. Instead of calling it off or setting any kind of boundaries, Tony waits for Kathy to go too far and then yells at her, fulfilling her need for his attention. Ultimately, Dare breaks into Tony's apartment and shoots him, causing him severe injuries that continued to plague him for years. This story is really that dark! There's no possible positive conclusion to draw.
There's really not much to say about Indries Moomji—other than the fact that she basically walked up out of the blue and crushed Tony Stark to oblivion without even breaking a sweat.
Hired by Obadiah Stane to make Tony believe she was in love with him, Indries fed the affair as long as she knew she needed to, then coldly dropped Stark by sneering about how impossible it would be to love him. Seriously! See what I mean when I say that Tony Stark is actually kind of sympathetic sometimes? Sure, he's a jerk, but everyone he dates is only trying to get close to him to kill or ruin him, so I get it!
Indries more or less vanished after her brief role in Tony Stark's demise and the loss of his fortune to Stane, but I still hold a strange level of respect for her because she was raised in a cult and apparently has zero remorse for anything she does.
This is where even the strongest Tony Stark stan will have to take a step back and admit that this guy makes pretty consistently terrible choices in terms of trying to play the hero for women he has no business getting involved with.
Born Giulietta Nefaria, the daughter of a guy literally named Count Nefaria, Masque was adopted and renamed Whitney Frost. Her father comes back into her life later and promptly ruins it, sending her down the spiral that leads her to become first a crime boss, then a supervillain after her face is permanently scarred in an explosion. Hence, she becomes Madame Masque, a ruthless criminal mastermind. This leads to her an encounter with Tony Stark, who decides flirting with the daughter of a deadly enemy is probably a great idea.
Masque goes to some length to reconnect with Tony by literally taking on a fake identity and getting a job as his personal secretary. Although he soon discovers her secret identity, he pursues a relationship with her anyway. TONY! What is your deal?! Everything is going... well, weirdly, to be frank, until one day Iron Man sort of on purpose causes the death of Masque's father and she breaks up with him.
Most of the time when Masque shows in the comics now, she's unhinged and easily fooled into believing Tony is in love with her again. She also created a lot of evil robot versions of herself and set them loose on the world for the Avengers to deal with—so based on that alone, she's pretty likable. This is definitely another one of Tony Stark's exes who is out there desperately trying to murder him, but at least he's probably used to that by now.