Did She Really Go Out With Him?

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 5:00pm on MTV), we take a look back at some of Hollywood's most mismatched couples.

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.

Oh, Jennifer Aniston, how we wish you would just give up on John Mayer forever. Prone to holding impromptu press conferences regarding the details of their relationship, the musical wordsmith can't seem to overcome his crushing self-love enough to treat America's sweetheart right. Don't you know, John Mayer, that Rachel Green and the Hair That Inspired a Generation will always win our favor, no matter how many classless publicity stunts you pull?

Audrina Patridge's epic relationship with Mayor of Scraggle Rock Justin "Bobby" Bresica bewildered just about everyone — including her "Hills" friends, whose own boyfriend choices have also been pretty questionable. Even considering his infidelities and famous inability to understand restaurant menus, Audrina continually defended the aspiring hairdresser until the bitter end. With a rumored romance brewing with Kristin Cavallari now that the two have finally split, it seems the charmer has now moved on to dating his ex-girlfriend's friends. Or fake-dating her friends for fame on a television show. Either way, we don't like what he's got to offer.

Another selection from "The Hills" Hall of Fame of Sucky Boyfriends is Jason Wahler, the ex that led Lauren Conrad to obtusely abandon her Parisian dreams. Jason is almost as familiar with legal trouble and infidelity as he is with Mystic tan, so we were pretty proud when LC finally told him to pack up his chin strap and go. Orange you glad the tanorexic fame-leech is out of your life, too, Lauren?

Mischa Barton is no stranger to scummy boyfriends. However, since she was dating a guy named Cisco Adler whose personal grooming choices conjure up the image of a 1970's porn star, we can't say we were surprised to hear that nudie photos of this guy surfaced in Paris Hilton's possession. We also can't say we were surprised they broke up.

Mischa Barton must be a serial d-bag dater, considering she also had a misguided romance with the guy even paparazzi labeled as "Greasy Bear". Brandon Davis's talent for colorful language likens him to a young Mel Gibson. Barton has since done a better job of avoiding people who seem less … wet, but with her track record, maybe we should be questioning Mischa and not the mistakes she dates.

Poor Minnie Driver. She's been dumped publicly so many times that the press has unfairly framed her as the Hollywood version of your sad, single friend. But come on, if you don't want that kind of rep, try not dating someone like Criss Angel. Presto! You're no longer being left for Paris Hilton or whoever.

One of the most horrific dating nightmares of the last decade was Elizabeth Hurley's romance with billionaire Steve Bing. After getting impregnated by the gent, the befuddlingly beautiful model/actress was forced to messily establish his paternity through the British legal system, even though the baby came out looking like a hairless baby-Bing. Here's to her subsequent marriage to another rich, yet devastatingly handsome, businessman.

The consummate odd couple of Serena Williams and Brett Ratner continues to boggle our minds long after they broke up. The Hollywood filmmaker's sleazy reputation, which may or may not have originated from his openness with the press about his sexual exploits with transvestites, just doesn't fit with our image of the mega-talented athlete. Thanks for coming to your senses, Serena.

Say what you will about Kim Kardashian, but she has one talent you can't deny: being hot. So we're not sure what would motivate her to date, much less make a deeply shocking sex tape with, someone whose sole claim to fame was being Brandy's little brother and having a name that rhymes. I mean for the love of Ray J, what was she thinking?!

This couple, who met on the set of "One Tree Hill," shared but a few months of wedded bliss before Chad Michael Murray decided to stray, purportedly cheating with an authentically high school-aged extra from the show. We hope you find love again, Sophia Bush, and maybe this time with a guy who doesn't have three first names?

While the integrity of Lindsay Lohan's relationships has always been rather questionable, no one deserves the treatment that sleazy cueball Calum Best gave the troubled starlet after they broke up. Not only did he falsely (we think) claim they made a sex tape, but he also took credit for turning her into lesbian. Real classy.