Drew Barrymore and Tom Green: 5 Months

Actress Drew Barrymore has had her fair share of relationships, but it was her love affair with comedian Tom Green that had captured all the news headlines. They met on the set of “Charlie’s Angels” and started dating in 1999.

They tied the knot in 2001 and just a few months later, Green filed for divorce due to “irreconcilable differences.” They still have love for each other, and in 2021, Barrymore invited him to her show, “The Drew Barrymore how,” and that was the first time they met face-to-face in almost 20 years.