Mila Kunis & Macaulay Culkin
Can you believe Mila Kunis and Macaulay Culkin dated for nearly ten years? The couple began dating back in 2002, though despite their long courtship Kunis has been open about the fact that she always new Culkin was not “the one.” The two were able to confide in one another and share the stress of fame, though eventually, the romance died out for Kunis. Though swearing at age 16 that she didn’t believe in marriage she went on to marry Ashton Kutcher.
John Hamm and Jennifer Westfeldt
In 1997 Mad Men star John Hamm and Friends With Kids actress Jennifer Westfeldt started a relationship that would last many years. Hamm once said of their love, “We may not have a piece of paper that says we’re husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that. To me, people [should] get married when they’re ready to have kids, which I’m not ruling out.” The actor’s struggle with alcohol and his stint in rehab in 2015 seems to have coincided with the end of his relationship to Jennifer, as the two announced the end of their relationship that same year.