Drew Barrymore and Tom Green: 5 Months
Actress Drew Barry Barrymore fell in love with Tom Green on the set of the movie “Charlie’s Angels,” and it was love at first sight. They started dating and soon after, Green proposed to her during a vacation in Cabo. The couple eloped in the South Pacific, but 5 months later, they were dunzo. Barrymore remarried in 2012 and had two kids with Will Kopelman, but got divorced in 2016.