Who

The eldest daughter of The Donald, Ivanka is a former model, social fixture, reality TV star, jewelry designer, and—if she's to be believed—real estate executive.

Backstory

Donald Trump's daughter by his ex-wife Ivana, Ivanka had a predictably cushy childhood: Raised by a rotating cast of Irish nannies, she grew up in a marble palace atop the Trump Tower and spent vacations on her dad's lavish estate in Palm Beach. She first made a splash on the scene during her teen years, when she pursued a modeling career and appeared on the cover of Seventeen. (She's said that she "had to turn" to modeling to pay her bills, which is about as accurate as her father's claim that he's entirely self-made.)

After attending boarding school at Choate, Ivanka enrolled at Georgetown, transferring to her dad's alma mater Wharton after two years, and earning a burst of publicity as a junior when she appeared in Jamie Johnson's Born Rich. Following graduation in 2004, she spent a year working at Bruce Ratner's real estate firm before joining her dad's company. What, precisely, Ivanka's responsibilities entail these days as a vice president of real estate development at the Trump Organization (where her brother also works) is unclear.

Much like her father, though, Ivanka has bigger plans. She recently jumped into the jewelry biz with the "Ivanka Trump Collection" and opened a retail boutique on Madison Avenue. (A second boutique in Las Vegas is in the works.) And she clearly shares her dad's taste for the spotlight: When Carolyn Kepner was booted from The Apprentice, it was Ivanka who replaced her—and she now dons low-cut dresses and bares her considerable cleavage in ads for her dad's real estate projects. Of course, considering he paid for those things, it's only fair.

Personal

Ivanka dated Bingo Gubelmann for a spell (the cousin of socialite Marjorie Gubelmann) and has also been linked to Lance Armstrong and Topher Grace. In 2007 she seemed to find love with Observer owner (and fellow real estate scion) Jared Kushner. Alas, the couple split in early 2008, reportedly because Jared's mom objected to his expedition into non-Jewish waters. Ivanka lives in a two-bedroom apartment at the Trump Park Avenue on 59th and Park, which cost her (or her dad, rather) $1.5 million in 2004.

Soundbite

How's this for creepy? When Ivanka's dad appeared on The View, he offered up the following gem: "She does have a very nice figure. I've said if Ivanka weren't my daughter, perhaps I'd be dating her."