‘The Boys’: Were Homelander and Madelyn Stillwell Together? Relationship Explained

‘The Boys’ series gave us one of the most demented villains in a long time. Homelander is a troubled superhero who grew up in terrible conditions that gave rise to his cold-blooded personality as well as some unhealthy relationships. One such relationship was with Madelyn Stillwell, who served as a top-ranking executive of Vought Corporation. We’ve seen Madelyn crossing the boundary of professional on multiple occasions, and Homelander ultimately killing her in cold-blood. So, what was their deal? Were Homelander & Madelyn together? 

Homelander’s background led to a really complicated relationship with most women in his life

We know that Homelander was basically grown in a lab out of Soldier Boy’s semen and by using the so far unnamed woman’s egg. He was brought up in a sterile environment and didn’t exactly have normal, familiar relationships. He never went to school and was never properly socialized, so it’s no wonder that he developed some kind of sociopathic disorder. 

He was also exposed to a massive amount of torture so that his exact limits could be tested, which further desensitized him not only in regard to physical pain and hardship but mentally as well. It’s common knowledge that Homelander killed several of his female role models by accident, which further complicated his quest to attain a motherly role model. And this is where Madelyn comes in. 

Madelyn used Homelander’s broken personality to advance her own career 

Madelyn quickly figured out that Homelander seeks a strong motherly figure, something he never had while he was growing up, for several reasons. I mean, problems with mothers are not all that uncommon among the general population as well, but they could become dangerous quickly when you add to the equation an incredible amount of power. 

Homelander always sought the general public’s approval; he wanted to be loved and adored, and he wanted people to throw themselves at his feet. Madelyn was a strong role model in his life. She offered compliments when it was needed, she offered criticism where it was due, and she often talked to Homelander like a just mother, praising her son or calling him to be accountable for his deeds. 

But she also worked on protecting him, not out of unselfish motivations. By advancing Homelander’s status, she was also advancing her own career and status. 

Madelyn also offered sexual gratification when it was due, which was mostly obvious in the scenes where she calmed him down by using breast milk. But this was around the time when Madelyn’s tactics to control Homelander were beginning to be dangerous. Homelander felt like Madelyn’s son was “stealing” most of her attention. He felt like he was no longer in the spotlight. Madelyn felt that she needed to amp up her efforts to remain in control of Homelander through sexual and other measures. 

But the more Homealnder realized he was no longer Madelyn’s “golden and pure boy,” he was starting to feel less and less dependent on her approval. 

Were Homelander and Madelyn ever in love? 

Homelander and Madelyn Stillwell were never in love. Both were dependent on each other, but there was never any true love in the equation. When Homelander learned what Madelyn did with his son, and when he realized that her job was basically to control him, he figured that she was a liability and brutally eliminated her. 

Yes, he later hired a doppleganger to simulate Madelyn, but that was not out of love. That was a desperate attempt to keep any semblance of normalcy in his life. Following Madelyn’s death, he became even more dangerous. He was no longer tied down to his “one and only” perceived weakness. And he made sure not to make the same mistake as with Madelyn again. 

When Ashley Barrett took on Madelyn’s job, he made sure to show her from the start that he was in charge and that she responded to him. He also sniffed it out pretty early on that Ashely would be a terrible replacement mother for him due to her “lack of spine.” 

Homelander has a thing for strong women

Despite her lack of superpowers, Madelyn fits the stereotype of a strong career woman, and since Homelander was more often than not the strongest person in the room, it’s possible that he craved to be dominated on some levels, although he would never admit to it of course. 

This is further supported by the evidence that all of his known relationships in the past have been with aggressive and powerful women. He briefly dated Queen Maeve, who was the only member of the Seven that could meet with him on equal ground, sort of. Queen Maeve was also the only member of the Seven that Homelander respected to an extent, but as soon as he started losing control of her, he retaliated in the worst possible way. 

Homelander also dated Stormfront, a closeted Nazi. She was also incredibly powerful, but as soon as this “power” aspect ran out once she was horribly injured, Homelander used her to vent his pent-up sexual gratification.

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