#6 - Ivana Trump and Rossano Rubicondi

In April 2008, 400 guests watched as 59-year-old Ivana Trump, walked down the aisle and married boy toy Rossano Rubicondi, 24 years her junior. The $3 million wedding took place at Mar-A-Lago, the Palm Beach estate of her former husband, real estate mogul and businessman Donald Trump.

Early in December, she announced she had filed for separation - three months earlier. The news came after rumors that her young spouse was caught cheating while a contestant on the Italian version of the TV show "Survivor."

According to reports, Rossano had an on-camera affair with Argentinian model, Belen Rodriguez. Trump said she had not disclosed the separation because she didn't want to hurt his chances on the show, where he was eventually voted off.

It was the fourth divorce for the Czechoslovakian-born model made a name for herself after marrying Trump in 1977. The couple met in New York shortly after Ivana divorced her first husband.

The Trumps' marriage ended in the early 1990s when she discovered he was having an affair with Georgia-born beauty queen Marla Maples. Her settlement, which is sealed, was rumored to be at least $20 million.

Not long after her divorce from Trump, Ivana married Riccardo Mazzucchelli, a coupling that lasted less than two years. She dated Rubicondi on and off until marrying him in 2008.