Human Interest Elon Musk's College Sweetheart Puts Gifts, Photos Up for Auction to Pay for Stepson's Education: 'A Snapshot' Photographs of Elon Musk taken in the mid-1990s during his relationship with college girlfriend Jennifer Gwynne are currently up for auction. Through RR Auction, Gwynne is selling 21 items from the couple's year together as students at the University of Pennsylvania. They include images of a "silly" Musk taken long before he became the CEO of companies such as Tesla and SpaceX. By Jason Hahn Jason Hahn Jason Hahn is a former Human Interest and Sports Reporter for PEOPLE. He started at PEOPLE's Los Angeles Bureau as a writer and reporter in 2017 and interviewed the likes of Kobe Bryant, Arnold Schwarzenegger and Tom Brady. He has a B.A. in English from the University of California, Berkeley, and a Master's degree in Journalism from Columbia University. He previously worked for Complex Magazine in New York City. People Editorial Guidelines Published on August 25, 2022 11:43 AM Share Tweet Pin Email Trending Videos Photo: RR Auction 01 of 10 Elon Musk Driving His BMW, 1995 RR Auction Gwynne says this picture of Musk in his car was taken in Philadelphia while on their way to see Pulp Fiction. "His brilliance and his vision was balanced with a bit of wide-eyed wonder back then," she tells PEOPLE. "I think these items are a snapshot of who Elon was just before he started to conquer the world," she adds. "The photos show his less serious side — his silly, come-play-with-me attitude which would pop up now and then. His everyday quiet intensity was really what attracted me to him initially... I'm a sucker for tall, blonde, and nerdy." (PEOPLE reached out to Musk's representatives for comment about the auction.) 02 of 10 Musk Having a Drink at an Apartment at Queen's University, 1994 RR Auction The picture of Musk holding a glass was taken while Elon took Gwynne on a trip to meet his family. During the trip, they stopped to meet his brother, Kimbal, at Queen's University in Canada, she says. 03 of 10 Musk Visiting the San Francisco Bay, 1995 RR Auction Gwynne says this picture of Musk was taken in San Franciso after she returned from studying abroad in London. She admits the relationship had begun to run its course by this point. "Things for us weren't going very well during this visit. Elon was not very good at a long-distance relationship," she said on the auction house's website. "Talking on the phone seemed like a waste of time to him—NOT what a 20-year-old woman wants to hear. We broke up soon after I left San Francisco and headed back home to Rhode Island." 04 of 10 Musk Hanging Out in a Dorm Room, 1994 RR Auction Gwynne says Musk was hanging out in her Quadrangle dorm room when she snapped this picture. 05 of 10 Musk Visiting Gwynne's Mother in Rhode Island, 1995 RR Auction Gwynne, who calls herself a "hoarder of anything sentimental," says the auction came about because it finally felt like time "to let these things go." "I've been watching Elon's assent over the past 25 years or so – initially, it was just articles in UPenn alumni magazines, and now, of course, it's Time magazine covers and Twitter headlines," Gwynne tells PEOPLE. "And I would always tell my sister that someday I was going to sell the card with his signature on it, knowing it would be valuable (I'm a hoarder of anything sentimental I've ever been given)." "Now is just the time to let these things go," she adds. "I know an Elon Musk fan would enjoy them even more than me, and my husband and I are looking toward saving for my stepson's college education." 06 of 10 Musk Wearing a 'Judge Dredd' Shirt, 1994-1995 RR Auction In this picture, Musk wore a shirt with the logo of the popular comic book character Judge Dredd while at a study hall at the University of Pennsylvania, Gwynne says. 07 of 10 Musk Birthday Card to Gwynne, 1994 RR Auction Among the items up for auction are a 14k gold necklace with a small green emerald that Musk gifted Gwynne for her birthday in 1994, as well as a birthday card that calls her by a nickname: "boo-boo." "The emerald necklace and the birthday card are examples of his truly romantic side – which was also hard to catch glimpses of," she tells PEOPLE of Musk. "When he gave me the necklace and note, I saw the part of himself that he was offering to me, and it made me love him more." 08 of 10 Musk at a Philadelphia Restaurant, 1995 RR Auction When Musk and Gwynne were dating, they both worked as Resident Advisors for the university's dorms. Though they tried to keep it secret, Gwynne told the auction house, many people knew. "We had gone as an RA team out to eat in 1995. As RAs on the same team, technically we weren't allowed to date each other, so we just pretended not to—but everyone on the team knew and so did our boss," she wrote on the auction house website of a team outing to a restaurant in 1995. "We purposely sat away from each other, but when I walked around taking pictures of each table, I made sure to get this shot of him.' 09 of 10 Musk Works at a Computer, 1995 RR Auction Gwynne tells PEOPLE: "My time at UPenn and my time dating Elon was amazing. I was blessed to be offered that level of education and to meet friends and classmates like Elon. And I can always tell the stories of Elon predicting the future of electric cars well before I passed them on the road every day. But I also have the memories of Elon's family welcoming me into their home in Toronto during the holidays in 1994. I know Elon, Kimbal, Tosca, and the gracious supermodel Maye Musk are a tight tribe, but for a brilliant couple of days that winter, they let me be part of it." 10 of 10 Musk Inside His BMW, 1995 RR Auction Gwynne told RR Auction this photo of Musk was taken shortly after he started the company Zip2. The auction for the items will run until Sept. 14, 2022. "The auction came about because of the Jeff Bezos' $28,000,000 rocket seat sale as well as with the Musk graded homework," Bobby Livingston, Executive Vice President RR Auction, tells PEOPLE. "RR Auction is a leading auction house of historical science, tech hardware and memorabilia related to the pioneers of the last 50 years. Our clients are some of the most successful tech entrepreneurs and advocates."