33. Drew Barrymore and Will Kopelman

Drew Barrymore was once married to Will Kopelman, who is the son of former Chanel CEO Arie Kopelman. Even before they got romantically involved, Kopelman and Barrymore were already good friends. Their relationship began in 2011 and in December of that year, they got engaged. At that point, Barrymore was pregnant with their first child. In June 2012, they tied the knot. A few months after their wedding, Barrymore gave birth to daughter Olive. They have another child, daughter Frankie, who was born in 2015. Thanks in part to Barrymore’s early life, the couple wanted to raise their children in a highly traditional setup, away from the cameras and the spotlight.

However, Barrymore and Kopelman’s relationship came to an end. In 2016, after four years of marriage, they called it quits. They agreed to co-parent their children and have made investments for their children. In later years, Barrymore said that she took the split from Kopelman ‘really hard’. Today, Barrymore is single and has made no plans for another relationship, opting to focus on raising her kids instead. Meanwhile, Kopelman has been engaged to writer Allie Michler since January 2021.