While Spider-Man has always had problems in his romantic life, no one in Marvel Comics has had as many disastrous endings to a relationship as Daredevil. It seems like every woman Matt Murdock falls in love with either dies or leaves him because he can’t keep his personal life on track while working as Daredevil. He can’t be honest with any woman he is with, and those he is honest with have either betrayed him or died because they knew who he was. This makes him the most unlucky in love superhero in the Marvel Comics universe, and things are not any better now than they were four decades ago.
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From Daredevil’s girlfriends who have died to those who have betrayed him, and even worse, here is a look at the Marvel hero’s most tragic romances.
10) Kirsten McDuffie
Kirsten McDuffie is at the bottom of the list because her relationship with Matt Murdock didn’t end in tragedy or heartbreak for her. Kirsten was the assistant district attorney, and she knew Matt was Daredevil, although he always denied it to her. When Matt’s identity was revealed, Daredevil and Kirsten moved to San Francisco and started a law firm together, forming a closer romantic relationship. When the Purple Children caused the world to forget that Matt was Daredevil, he used this as an excuse to break up with Kirsten and went back to Hell’s Kitchen. Despite this, she returned to help when Daredevil was arrested for murder, and the two remain on friendly terms.
9) Glorianna O’Breen
Glorianna O’Breen was a girlfriend for Matt Murdock, but she was one of his least interesting. This is because Marvel Comics creative teams mostly used her as a damsel in distress for Daredevil to save her numerous times. This was one of the girlfriends who ended up dumping Matt, despite professing her love for him, because he kept lying to her and disappearing when he went off to act as Daredevil. Glorianna ended up dating Foggy Nelson, before Victor Krueller eventually murdered her when he was looking for people who served as witnesses in a case where Wilson Fisk tried to kill him. She was just one of several Daredevil girlfriends to die, but this happened long after they broke up.
8) Black Widow
Daredevil has also dated superheroes in his lifetime, and one of Daredevil’s best relationships was with Black Widow. They were allies for a long time in the comics, and for a long time, they became romantic partners as well as partners in the crime-fighting field. This was another case where the two broke things off, and there were no hard feelings afterwards. In fact, Black Widow has been there to help Matt more than anyone other than Elektra, and was even on call to help protect Matt’s future girlfriends, and even his ex-wife, when he needed someone to count on.
7) Echo
Echo and Daredevil had a very similar relationship as he did with Elektra. Kingpin had trained Echo to be an assassin, and he sent her to hurt Matt Murdock. However, Matt and Echo fell in love, although neither knew the other’s identity at the time. However, once they figured it out in the middle of a fight, Daredevil explained who Kingpin really was and what he was capable of. This caused Echo to betray Kingpin and turn into a hero like Matt. However, due to their careers as vigilantes, they broke off their relationship but still remained friends.
6) Nyla Skin
Nyla Skin is someone who returned to Matt Murdock’s life again in 2025, and this isn’t the first time they dated. Matt and Nyla dated before and were a strong couple, even though Nyla was a burglar when she first met an amnesiac Matt, who thought his name was Jack. After he regained his memory, he left Nyla so she wouldn’t be in danger. However, this year, Nyla was back in Marvel Comics and started dating Matt again. However, this lasted only a few issues before Nyla broke up with him because Matt kept disappearing, and she knew he was lying about what he was doing when he left. Knowing he couldn’t share his secret with her, the two agreed to part ways as friends.
5) Heather Glenn
Heather Glenn was someone who loved Matt Murdock, but never knew he was Daredevil while they dated. This is also what ruined their relationship. After Daredevil arrested Heather’s father and had him incarcerated, he discovered that the Purple Man was controlling him. Before he could get him out, Heather’s dad died by suicide while he was behind bars. Heather walked in on Matt while he was in costume and realized who he was. When he explained that her father had died, she broke up with him on the spot and ordered him out of her life. The two got back together and broke up several times, but soon she began a self-destructive turn and succumbed to alcoholism. Heather called Matt several times, but he had finally decided to end things for good. After this, Heather hanged herself in her home, dying by suicide, where Matt and Foggy found her body.
4) Elektra
Easily, Daredevil’s most toxic relationship is with Elektra. The two started out as enemies, with Elektra an assassin and Daredevil a vigilante. However, the two eventually became reluctant allies and eventually fell in love. This all ended in tragedy when Bullseye showed up and murdered Elektra before Daredevil could save her. Elektra ended up resurrected by The Hand, and the two have been on-again, off-again for years. In recent comics, Elektra is now operating as a second Daredevil and she works with and help Matt when she can, and while he wants more with her than they have, she has grown wise enough to keep him at arms-length for anything other than fighting together.
3) Typhoid Mary
Easily, the worst decision that Daredevil ever made when it came to a romantic relationship was with Typhoid Mary. Forget the fact that she is a supervillain and one of Kingpin’s main assassins. She is also mentally unstable, and Daredevil getting into a relationship with her could only mean bad things for her mentally and for him in the long run. Since several of Mary’s alters like to murder people, she was never going to be safe for Daredevil to be around, but he stuck with her anyway. This relationship was as toxic as anything Mary had with Kingpin, and Daredevil never seemed smart enough to know that just because he loved one of her alters, by getting involved with her, he was only hurting her in the long run.
2) Milla Donovan
Matt Murdock has been with several women in his life, but he has only been married once. Matt married a woman named Milla Donovan, who was born blind and grew up in Hell’s Kitchen, determined to improve the area. The two began to date after Daredevil saved her life, and she discovered that he and Matt were the same person. He fell for her so hard that he couldn’t lie to her about it, and the two fell in love and married. This, sadly, was when Matt was put in jail with Kingpin, and Foggy Nelson was seemingly murdered. With so much going on, it was too much for Milla, who tried to stand by Matt the entire time. She finally lost control of her mental wellness, and when she accidentally killed someone in a rage, she was institutionalized. Matt was ordered to stay away from her, as he was deemed the reason for her mental problems.
1) Karen Page
The most toxic and destructive relationship Daredevil ever had was with his greatest love, Karen Page. Fans who only know Karen from the Netflix and now Disney+ shows might be surprised to know how far she dropped in the comic books before her death. Karen became an addict and actually sold Daredevil’s secret identity for drugs, which is how Kingpin learned who he was. Kingpin used this information to destroy Matt Murdock’s life, and it was all because of Karen. What really capped it off was when Bullseye showed up at the church where Matt’s mother works as a nun and tried to kill Matt, only for Karen to sacrifice herself, dying in Daredevil’s arms, something that has happened to the hero one too many times in his life.
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