Macaulay Culkin and Mila Kunis
Considering they both started out as child actors, it's not too surprising that "Home Alone" star Macaulay Culkin and Mila Kunis, who rose to fame on "That '70s Show," started dating in 2002. Of course, the romance started long after Culkin had entered the "Where Are They Now?" files. The two ended up splitting in 2011, saying that the breakup was amicable and that they remain close friends.