Macaulay's longest-lasting relationship in the spotlight was definitely with Mila Kunis, whom he dated from 2002 to 2010. Despite being together for nearly a decade, they remained pretty low-key about it all. Mila was 18 and Macaulay was 21 when they first began dating, staying together through their 20s.
"We grew up together. You find a steady rock in your life and that's all you need. We have our ups and downs, but work through them," Mila told Women's Health in 2009, as reported by People. "I don't know if I met him at 27 if it would have been a different relationship."
In January 2011, news broke that the couple had split some months before. "The split was amicable, and they remain close friends," Mila's rep told Page Six at the time. Seven years later, however, Mila admitted that she "f*cked up" the relationship and its ending.
"[It was] a horrible, horrible breakup . . . I f*cked up. I was an ass in my 20s and I'll be the first to admit it," she revealed on Dax Shepard's Armchair Expert podcast.