Hollywood's hottest gurl dated a mysterious real estate developer?

What is it about Hollywood's hottest starlets that, despite their beauty, wealth and charm, makes them constantly date beneath them? In honor of the new show, "Is She Really Going Out With Him?" (airing Monday through Thursday at 5:30pm on MTV), we take a look back at some of Hollywood's most mismatched couples.

Anne Jacqueline Hathaway (born November 12, 1982) is an American actress. She made her acting debut in the 1999 television series Get Real, but her first prominent role was in Disney's family comedy The Princess Diaries (starring opposite Julie Andrews), which established her career.

She continued to appear in family films over the next three years, with lead roles in Ella Enchanted and The Princess Diaries 2: Royal Engagement in 2004. Hathaway would later venture away from the "G-rated" image her early acting career bestowed upon her, starring in the films Havoc and Brokeback Mountain. She later starred in The Devil Wears Prada, opposite Meryl Streep; Becoming Jane, in which she portrays Jane Austen, and Get Smart, opposite Steve Carell. In 2008 she earned widespread critical acclaim for her star turn in the film Rachel Getting Married, for which she won numerous awards, including a nomination for the Academy Award for Best Actress.

Her acting style has been compared to that of Judy Garland and Audrey Hepburn and she cites Hepburn as her favorite actress and Meryl Streep as her idol. People magazine named her one of 2001's breakthrough stars, and in 2006, she was listed as one of the world’s 50 Most Beautiful People.

Anne Hathaway dated a mysterious real estate developer named Raffaello Follieri (who just seemed like a more exotic and tanned version of Zach Braff) until last July, when a giant scandal exploded regarding his alleged fraud. Looking back on his smug poses and untrustworthy fabulous hair, the allegations of sliminess don't seem so far-fetched. With talent, commitment to charity and a plethora of successful films under your belt, Anne, we can't help but hope for your sake that your new flame doesn't participate in illicit extracurriculars.

Vati-Con is the nickname given to a scandal involving Italian real estate developer Raffaello Follieri, who is accused of misappropriating a $50 million investment from billionaire Ronald Burkle meant to buy up Roman Catholic churches in the United States

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