5 Women Who Should Have Never Dated Daredevil

Karen Page is definitely at the top of most lists for the most tragic relationship with a superhero. Her relationship with Matt Murdock starts out innocently enough when she is hired as a secretary at the law firm of Nelson and Murdock, but things soon took a turn for the worse. After various dangerous rescues, Matt reveals his superhero identity to Karen. This revelation makes her constantly fear for Matt's safety and he shows no sign of quitting his superhero ways. Karen ends the relationship with Matt and moves to California to pursue acting.

After this, Karen floats in and out of Daredevil's life for some time. She still holds the record for the longest lasting relationship with Matt Murdock. At one particularly dark point, Karen fell on hard times and became a pornographic actress while also starting a heroin addiction. She falls so low that she even sells Daredevil's secret identity to a dealer for more drugs and this information eventually gets back to the Kingpin. Her regret and desire for recovery lead her back to New York and Matt. Matt helps her overcome her addiction and they even move in together for a time. This happy status quo is shattered however, when Matt has an affair with Typhoid Mary and Karen leaves him yet again.

Karen and Matt ultimately mend fences but this happiness was not meant to last either. The villain, Mysterio, hatches a plan to mentally destroy Daredevil and creates a false blood test result for Karen, fooling her into believing she is HIV positive. She returns to Matt's life to warn him about her status and becomes entangled in a battle between Daredevil and Bullseye. Karen is killed by Bullseye during the fight when she leaps in the way of a lethally thrown billy club to protect Matt. Without Matt in her life, Karen may have had a chance at a normal and long life.