Hillary Clinton’s Boyfriend Before Bill Was David Rupert

Hillary Clinton boyfriend David Rupert


Former Secretary of State and Democratic presidential candidate Hillary Clinton is the subject of a four-hour documentary that dropped on Hulu Friday, March 6, simply titled Hillary. In the opening episode, the documentary mentions her boyfriend who was a “conscientious objector” to the Vietnam War. His name isn’t given, but the man is David Rupert.

Here’s what we know about their relationship.

Rupert Is the Second of Two Boyfriends Hillary Had Before Meeting Bill Clinton

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Hillary Rodham started at Wellesley College in 1965 and began dating a man named Geoff Shields, who went to nearby Harvard University. According to Carl Bernstein’s Clinton biography, A Woman in Charge, the two of them dated into Clinton’s junior year and had a very “normal” and “healthy” relationship. But during the summer of 1968, a new man came into her life: David Rupert.

Clinton met Rupert in Washington D.C. where they were both working that summer as Republican interns. Rupert was a Government major at Georgetown University student whom Clinton spoke of during an interview on Howard Stern’s radio show, calling him “really handsome” and saying that he resembled a “Greek god.”

Despite the Republican internship, Rupert told Bernstein that upon meeting Clinton, he could already tell she was struggling with the Republican ideals of the day, as he himself came to as well, and he liked her attitude.

“I thought she was attractive. I wasn’t knocked over by her, like ‘There’s a knockout,’ but that’s not what makes me go anyway … “What I found attractive was the mix of her character, her intellect, and a physical attraction. And we laughed,” Rupert told Gail Sheehy for her 1999 biography of Clinton called Hillary’s Choice.

Rupert became a conscientious objector to the Vietnam War and subsequently had to do alternative government service. He was assigned to Vermont and Bernstein writes that Clinton would visit him there on weekends. She eventually took him to a friend’s wedding and introduced him to her parents as her boyfriend.

Clinton’s friend Nancy “Peach” Pietrafesa calls Clinton and Rupert’s romance “an intense love affair.”

“Hillary was always attracted to arrogant, sneering, hard-to-please men, like her father,” Pietrafesa claimed, saying that Rupert fit the bill. They dated for three years; in fact, he was her boyfriend when she met her future husband.

Enter Bill Clinton

However, Clinton would soon meet Bill Clinton, a fellow Yale Law School student. According to the Bernstein biography, she was still dating Rupert. The two of them would spend weekends together in Vermont with another couple.

But one day in the spring of 1971, Hillary noticed Bill looking at her in the law library and went up and introduced herself. Bill says in the Hulu documentary that their first meeting was pretty much it for both of them.

“I found her magnetic … I just had this feeling that this was not going to be normal and this could change your life and I don’t know about this. I’ll never forget, that was the first time I saw her. … She was different than anybody I ever met. The more time I spent with her, the better I liked her,” says Bill.

Hillary echoes his sentiments, saying in the documentary, “We were serious almost from the beginning. Bill is just, for me, in a different universe. A different level of connection. He is so incredibly charismatic, filled with positive energy, really smart. I just felt like he was the most interesting man I’d ever met and probably ever would meet and that I would never have a dull or boring moment and that has proven to be true.”

While it sounds like love at first sight, Rupert asserted in the Sheehy biography that the main reason Clinton dumped him for her future husband was that he wasn’t ambitious enough.

“She didn’t know how to be comfortable pursuing political ambitious for herself,” said Rupert, adding, “I think my lack of desire to be in a political role, having done that in Washington and then having gone to VISTA (a domestic Peace Corps), was something of a disappointment to her … I never stated a burning desire to be President of the United States. I believe that was a need for her in a partner.”

All four episodes of Hillary are out now on Hulu.

READ NEXT: What’s New on Hulu in March 2020

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