Make a list of all the characters in your icons. (Although you may have more than one icon of a single character, they only go on the list once.) Alphabetize it. Take the first two people on the list; that's your first pairing. Second two people; second pairing. etc.
Bobby/Brian. This idea just breaks my brain. It'd be pretty, though. *G*
Draco/Gabe. Draco would so be his bitch.
Greg House/Jack Sparrow. Huh. *looks at Vi and Ash* What do you think, guys? ;)
James Wilson/Justin Taylor. And people thought BRIAN was robbing the cradle...
Kaworu/Lucius. Okay, I think Lucius is hot and all, but this one just makes me go eurgh.
Mimi/Rob. ...Huh. Nothing wrong with dating a doctor, Meems. :D
Roger/Ron. *DIES LAUGHING*
Samwise/Satine. ...Huh. I got nothin.
Shinji/Stewie. Oh look, Shinji paired with someone his own emotional age. :P
Which leaves Will Turner all alone, which is as it should be, since I have no Elizabeth icons. ;)