Let's start with his first boo, Elektra. The two meet in college, but their idyllic romance is interrupted when her father, a Greek politician of questionable daughter-naming skills, is murdered right in front of them:
Matt hasn't even noticed he put on his bandana too low.
Years later, Elektra runs into Daredevil and quickly realizes he's Matt (there aren't a lot of blind guys with sick ninja moves out there). Unfortunately, she also runs into a big-ass knife:
Her last words are, "Hey, I just saw the Jennifer Garner movie based on me. Can you do me a favor?"