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Making good girl Anne Hathaway look bad is no easy feat, but her longtime boyfriend has managed to pull it off by allegedly committing check fraud. Raffaelo Follieri, Hathaway's 29-year old Italian real estate developer boyfriend, was apparently ordered by a D.C. court to pay up $250k in overdue payments to a PR firm, but the check bounced and the NYPD has placed him in custody. Worse yet, sources tell TMZ that when "the bank said insufficient funds, it wasn't even close." Considering we're still worried about paying next month's rent, we'd never deem having less than a quarter mill in the bank embarrassing, but taking Follieri's fancy name and job tile into account, we're thinking it's time Anne found some new arm candy. Especially since this isn't the guy's first run-in with the law...

April is apparently the cruelest month for Follieri, who was under investigation one year ago for attempting to thwart part of a $55 million investment from real estate magnate and Hollywood hanger-on Ron Burkle. Burkle sued Anne's boy for claiming the entire amount would go towards developing land for the Catholic Church, and reportedly using $1.3 million to spoil the couple's dog and take Hathaway on private jet trips. Though the couple has been together for years, Anne has a rock solid reputation of avoiding salacious tabloid stories and a career coming up roses. Her upcoming part opposite Steve Carell in Get Smart will ideally move her from chick flick dynamo to comedy star the way Katherine Heigl managed to ride her killer smile in Knocked Up into A-list territory. We can only hope Follieri's second trip on the criminal tabloid train will finally convince Anne to wash that man right out of her flawless hair.

[Photo Credit: Wireimage]