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Ivana Trump and shared a tempestuous, nearly 20-year bond that began in 2002 and lasted until his tragic death in October 2021. Despite a 23-year age gap and a short-lived marriage, Rubicondi was often described as the "tragic love affair of her life". A Lavish and Brief Union

However, the marriage was strained by geographical differences and professional conflicts. By September 2008, only months after the wedding, Ivana filed for a legal separation. They officially divorced in 2009, with Ivana famously citing the difficulties of long-distance romance: "Rossano wants to live in Miami and work in Milan... but I am a New Yorker". The Eternal "On-and-Off" Companion

After dating for six years, the couple married on April 12, 2008, in a $3 million ceremony at Mar-a-Lago . The event was hosted by Ivana’s former husband, Donald Trump , and officiated by his sister, Judge Maryanne Trump Barry.

Despite their divorce, the two remained inseparable for much of the next decade.