The Nature Boy’s third and fourth marriages were much shorter relationships than his first two. According to Heavy, his third was fitness instructor Tiffany Vandemark. It was riddled with financial problems and physical abuse. He tried to use Tiffany’s engagement ring as collateral on a loan. She allegedly hit him in the head with a phone charger. Flair also accused Vandemark of stealing wrestling memorabilia, such as robes he’d used in the ring and other personal items of Flair’s, and selling them to fans. The two separated within two years of their wedding, and were divorced in 2009.
Flair’s fourth marriage, to Jackie Beems, was also short and intense and fraught with violence. CBS News reported in 2010 that Beems had been arrested after she physically attacked Flair, leaving him “bloodied and bruised.” Beems accused him of conducting several affairs, a complaint that his previous wives had, as well, and the two were divorced in 2012.
For his fifth go at wedded bliss, Flair decided to wait until the calendar changed a couple times to tie the knot again. He actually dated Wendy Barlow (pictured with Flair above), a former WCW colleague of his, for a few years, rather than jump right back into that married life. They do fun things together like go on Celebrity Wife Swap with Rowdy Roddy Piper and his wife Kitty in 2013. The two were married in 2018 and appear to be doing well today.