#3: Elektra (Daredevil #181)
Daredevil doesn’t have the best luck with women. On his watch, the deranged assassin Bullseye murdered two of his girlfriends, and his wife, Milla Donovan, suffered a psychotic breakdown after Mr. Fear exposed her to anxiety-enhancing drugs. The most memorable of these tragedies has to be Elektra’s murder at the hands of the villainous Bullseye. After he gutted Elektra with her own weapon, she had to crawl to Daredevil’s front door for one last embrace. The image of Matt Murdock (Daredevil's alter-ego) hugging a dying Elektra one last time is truly heartbreaking. Of course this all could have been avoided if Daredevil had been out hunting down Bullseye himself instead of kicking back and watching TV in his apartment. Makes us look like great boyfriends.