Drew Barrymore and Luke Wilson
During the 1990’s, Drew Barrymore and Luke Wilson began dating, becoming the fixture of attention and one of the It couples on the scene. They even starred in some films together like Charlie’s Angels: Full Throttle. Barrymore recently opened up on her show and revealed that the two were in an open relationship since they were both young, just having fun, and felt that the relationship was very “low stakes.”
Drew Barrymore And Luke Wilson (Ron Galella, Ltd./Getty Images)
Madonna and Sean Penn
In January 1985, when Madonna was filming the music video for her song “Material Girl,” she met actor Sean Penn on the set. They began dating and by August of that year, the two were married when she was 27 years old and he turned 25 a day after. Following a turbulent relationship, Madonna filed for divorce in December 1987, but withdrew two weeks later. In January 1989, she filed once again and this time they were through with the divorce.
Madonna And Sean Penn (Alamy)
