I would...
Shag: Jim Carrey
Marry: Mark Ruffalo
Dump: Elijah Wood
and their connectin was Eternal Sunshine of the Spotless Mind
Hmmmm, we haven't done girls in awhile...how 'bout ... Reese Witherspoon, Brittany Murphy, Brooke Shields
"He's Mister White Christmas, he's Mister Snow. He's Mr. Icicle, he's Mister 10 below."