Chelsea's Exes

As the former first daughter gets ready for her secret nuptials this weekend to Marc Mezvinsky, a look back at the guys she left behind. VIEW OUR GALLERY.

Matthew Pierce

In 1998, when Chelsea was just 18, her love life made front pages with news that she was allegedly dumped by college boyfriend Matthew Pierce. "Chelsea's Heartache," the New York Post screamed—accompanied by a teary-faced image of the teenager—after Clinton turned up at Stanford's medical center seeking help for stress. The incident prompted a backlash against digging into Chelsea's private life that defined her relationship with the press for years to come. The New York Post also reported that the break-up was an indirect result of Bill Clinton's Monica Lewinsky scandal, which apparently traumatized Chelsea and led her to rely very heavily on Pierce when she went back to Stanford. Incidentally, Pierce was on the swim team at the college, sharing a team with Clinton's next boyfriend, Jeremy Kane.

AP Photo

Jeremy Kane

Like father, like daughter: In late 2000, as the First Daughter took on a number of official duties while her mother was running for the Senate, word broke that Chelsea, then 20, was dating Jeremy Kane, a fellow student at Stanford—and a summer speechwriting intern at the White House. In fact, the pair had already been seeing each other back at Stanford, according to pals, where they were both students. "They were best friends before they dated," one said, while another noted they shared a passion for politics. Having dined with the twosome after a San Francisco Giants game, the football team's COO Larry Baer was equally impressed. "They were like a couple who had been together for years," Baer reported. "Lots of people paid attention to Chelsea—Chelsea paid attention to Jeremy." The romance seems to have fizzled after 18 months, and then Clinton took off to Oxford, where she met her next beau, Ian Klaus.

Matt Campbell, AFP / Getty Images

Ian Klaus

Growing up surrounded by high achievers, Ian Klaus was a natural choice for Chelsea Clinton. A Rhodes scholar at Oxford (where he met Chelsea) and star player on his college's soccer team, Klaus went on to earn a Ph.D. in history at Harvard and publish a well-received book on Kurdistan, curiously titled Elvis Is Titanic at the age of 28. The pair split in late 2005 after a three-year relationship. Sources say they simply grew apart, with a friend reporting that Chelsea had begun answering questions about Klaus with only a "shoulder-shrug kind of answer." Of course, Klaus' dangerous book research in Kandahar—which produced sensational headlines like "Chelsea Collapses! Lover Caught in Iraq Bomb Blast"—couldn't have helped much.

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Ben Affleck

Chelsea came very close to exiting the White House without a Hollywood controversy on her hands, but when she and her father were mere weeks from leaving office—and the U.S. was captivated by the undecided presidential election—tabloids began circulating rumors that Ms. Clinton had ignited an affair with Hollywood heartthrob Ben Affleck, who had recently ended his relationship with Gwyneth Paltrow. Though the claims were outlandish, there were pictures to suggest a connection: Affleck is an avid supporter of the Democratic party and both Clintons, and he and Chelsea were reportedly snapped by Star magazine sharing a laugh at a birthday party for Hillary. Luckily for the scandal-plagued Clinton clan, other media outlets were hesitant to put any stock in the story, and it's now largely forgotten.

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Marc Mezvinsky

With investment banker Marc Mezvinsky, whom she will reportedly marry on July 31 in Rhinebeck, New York, Chelsea has found a future husband much like herself. Like Chelsea, Mezvinsky's parents are both politicians; his mother, Marjorie Margolies-Mezvinsky, served one term as a U.S. representative from Pennsylvania, while his father served two terms in the House representing Iowa. Another parallel: Mezvinsky's father had his own political scandal, an embezzling scheme that landed him in prison. The two have known each other since they were young: In 1993, each of their parents attended a Democratic summit in South Carolina, where they met for the first time. Later, Mezvinsky gave Clinton a tour of the Stanford campus before she enrolled. Though there were other suitors after that time, they rekindled their romance—with the President's approval. "He's great. He's a great human being," Bill said after their engagement was announced.