The Men Hillary Dated Before Bill

Hillary and Bill Clinton have been in the public eye for decades now. We've watched as their hair, eyewear, and clothes have progressed throughout the '80s, '90s, and early 2000s. We've seen them through some great times and some, well, not-so-great times (cough). It's pretty difficult to imagine them without one another, but believe it or not, there was a time when they didn't yet know each other. Like most married couples, Hillary and Bill dated other people before starting their own romance. So — who did Hillary Clinton date before she married Bill?

When Bill was running for president in 1993, a joke about the couple circulated: The Clintons are driving in Hillary's hometown and when they stop to get gas; Hillary notices the station attendant is her high school boyfriend. As they leave, Bill says, "See, if you’d married him, you’d be working at a gas station.” Hillary replies, "If I’d married him, he’d be President."

One of Hillary's ex-boyfriends even claims she broke up with him because he wasn't ambitious enough — i.e. he didn't want to be president some day. If that's the case, who are Hillary's past flings that could've been our 42nd president?

Here are a couple of people that Hillary dated before she met Bill...

David Rupert

When Bill and Hillary met at Yale in 1970, she was dating a different man: David Rupert. Hillary and Rupert dated for about three years after they met in the summer of 1968. Hillary was studying at Wellesley, and Rupert was a student at Georgetown. He claims the then-23-year-old broke up with him because he lacked ambition.

"I never stated a burning desire to be President of the United States," Rupert told The Guardian. "I believe that was a need for her in a partner." While that may or may not be true, she could have just been infatuated with Bill.

Jeff Shields

Before Rupert, there was Jeff Shields. Hillary started dating the Harvard student her first year at Wellesley in 1965. They saw each other almost every weekend throughout her first few years of college, taking hiking trips to Cape Cod and Vermont and having long political discussions.

"The thing that I remember most were the conversations," Shields told Vanity Fair. "She would rather sit around and talk about current events or politics or ideas than to go bicycle riding or to a football game." Shields was a lawyer in Chicago before becoming the Vermont Law School president and dean. He passed away in 2014.

Images: Vermont Law School (1)