Character names: Dan Humphrey & Serena van der Woodsen
Years dated in real life: 3

For the better part of three years, Blake Lively, who recently wed Ryan Reynolds, was romantically linked to the CW show's "Lonely Boy," Penn Badgley. During that time period, Penn's character, the loser turned hipster writer Dan Humphrey, was also getting it on with Blake's character, New York socialite Serena van der Woodsen. Their characters have been embroiled in a drama-fueled back-and-forth with the likes of Chuck Bass and Blair Waldorf for years.