1. Drew Barrymore & Tom Green – Five Months

When actress Drew Barrymore started dating comedian Tom Green, many raised an eyebrow. After all, Barrymore had become a successful actress by that point, while Green’s loudmouth humor was not to everyone’s tastes, to say the least. Regardless, the couple became engaged back in July 2000. Afterward, they spent almost a year fueling the rumors that they’d eloped. However, it wasn’t July 7, 2001, that they officially said: “I do.” Unfortunately, just five months later, the couple separated.
In a statement, Barrymore said, “Yes, it is true we have decided to part. I love Tom very much. He has always been a great friend, and that won’t change.” Meanwhile, Green said, “Drew is a wonderful woman, I love her very much. I wish our marriage could have worked out; I wish her much happiness.”
2. Carmen Electra & Dennis Rodman – Six Days

Carmen Electra began dating NBA star Dennis Rodman back in 1998. Soon after, Electra and Rodman got married in Las Vegas after a whirlwind months-long romance. While the couple’s marriage officially lasted six months, it actually took only six days for Rodman to file for an annulment. The basket player claimed that he was drunk when he tied the knot.
Meanwhile, Electra agreed that they had made a mistake. For her, she claimed she was still getting over the devastating loss of her mother. The model said she felt emotionally unstable, which led to the wedding. “Our relationship was very passionate,” Electra recently said, looking back. “When it was good, it was amazing.”