The Rapper: Rick Ross
The Singer: Ciara
Why They Should've Hooked Up: The ultimate payback for 50 Cent! Fif started his year by beefing with Ci-Ci on Twitter. Ross also has a penchant for dating 50's exes—he kicked it with actress Elise Neal for awhile. And, not for nothing, Ciara could certainly use the boost for her career that would come with dating the Boss. Quick: Someone arrange this before the ball drops on NYE!