She dated Elon Musk at Penn, and saved a lot of their stuff. Want a memento?
"Life is weird," Jennifer Gwynne said of dating someone who went on to become the richest person in the world.
According to a quote from Jennifer Gwynne on the RR Auction website: "Over Christmas break of 1994, Elon invited me up to Canada to meet his family and spend the holidays with them. Our first stop was to visit his brother, Kimbal, who was studying at Queen’s University in Kingston, Ontario, Canada. Elon had studied at Queen’s University before transferring to Penn in Philadelphia. After Queen’s University, we headed to his mom’s (Maye Musk) lovely apartment in Toronto. This picture was taken at Kimbal’s student college house that he shared with several other guys. Oh, this place was so nasty college gross; looked like it had never been cleaned and all the guys had padlocks on their door when they were out. We were having drinks before heading out to a formal holiday party. I was initially nervous because I didn’t have anything to wear. But Kimbal’s female friends were very kind and lent me a dress."Read moreCourtesy of Jennifer Gwynne / RR Auction
Jennifer Gwynne was a junior at the University of Pennsylvania when she met Elon Musk at a staff meeting for resident advisers.
Musk, then a senior, served as an RA at a freshman dorm next to the one Gwynne oversaw. One day, he knocked on her door.
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“He showed up at my room with some Chinese food and asked if he could come in,” she said. “And I’m like ‘Of course, if you brought me food.’ ”
Within a few weeks, the two became an item and dated for nearly a year, from 1994 to 1995, taking trips to Toronto to visit Musk’s family and to Rhode Island, to visit Gwynne’s family.
But after Musk graduated and moved to California, where Gwynne visited him once before she returned to Philly to finish school, the relationship fizzled out.
“I go on record that it was mutual, because I don’t remember getting dumped,” Gwynne said. “We left on great terms.”
In the years since, Gwynne has watched her high-profile ex-boyfriend found company after company, from Tesla to SpaceX. This year, Musk toppedForbes’ World’s Billionaires list with an estimated net worth of $219 billion.
So what’s it like to see your ex become the richest person in the world?
“Life is just weird,” Gwynne said. “It’s hard to explain how weird it is, but to me, he is just my first college boyfriend.”
Now Gwynne, who lives in Columbia, S.C., and works for a large medical supply company helping to launch new products, is auctioning off photos and mementos of her time with Musk, in part, to help fund her 13-year-old stepson’s college tuition one day.
She was inspired to do so after seeing a story in December about how a homework assignment Musk graded while he was a teaching assistant at Penn’s Wharton School brought in $7,753 at an online auction by RR Auction of Boston.
“I ran upstairs and said ‘What do I have?’” Gwynne recalled. “With his media presence, I’ll get the most ROI right now. As a Wharton grad, he’ll appreciate that.”
Among the items Gwynne is auctioning through RR Auction are more than a dozen never-before-seen photos of Musk, including one of him in a Judge Dredd T-shirt, one of him in a tuxedo, and one of him in a trench coat holding a gallon of orange juice. Gwynne is also selling an emerald necklace Musk gave her and a card, in which he wrote: “Happy Birthday Jennifer (aka Boo-Boo) Love Elon.”
When asked if Boo-Boo was his nickname for her, Gwynne said: “It was after I needled him for not calling me something sweet.”
And did she have a sweetheart nickname for Musk?
“Oh God no,” Gwynne said. “He was Elon.”
Bobby Livingston, executive vice president of RR Auction, said Gwynne’s collection is unique because there’s not a lot of Musk material in the marketplace.
“This gives you an insight into Elon Musk that you just don’t see. The way he interacts with the public now he’s a towering figure in our world and … here he is a college student having great time with his girlfriend,” Livingston said. “These are just fabulous clues into the personality of Elon Musk.”
According to a quote from Jennifer Gwynne on RR Auction's website: "After we finished up the holidays in Toronto, we drove back to the U.S. in his BMW and stopped to visit my family in North Providence, Rhode Island, as we made our way back to Philadelphia for the start of the Spring 1995 semester. While we look drunk, this is just a picture of us being lazy and affectionate hanging out with my siblings. This was taken in my brother’s room and for some reason, Elon wanted to look at my Penn student ID which was in my wallet."Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "This is a picture of Elon at my mom’s house in North Providence, Rhode Island. We had just arrived from the long drive and were raiding the fridge."Read moreCourtesy of Jennifer Gwynne / RR Auction
Elon Musk, front, and Jennifer Gwynne, back, are pictured with another University of Pennsylvania student during a resident advisor staff meeting.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "This picture was taken in my dorm room in the Quad at Penn. Elon was usually very reserved, but occasionally he would just get very silly and just want me to laugh along with him. So I decided to document him actually smiling."Read moreCourtesy of Jennifer Gwynne / RR Auction
A photo of Elon Musk in a Judge Dredd t-shirt taken by Jennifer Gwynne at a study hall at the University of Pennsylvania.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "This was a picture taken at a restaurant in Philadelphia. We had gone as an RA team out to eat in 1995. As RA’s 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. 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."Read moreCourtesy of Jennifer Gwynne / RR Auction
This photo of Elon Musk was taken during the summer of 1995, when Jennifer Gwynne went to visit him in California. According to a quote from Gwynne on RR Auction's website: "We were still a couple at this point, and this was just as Elon was beginning his conquest of Silicon Valley with the founding of Zip2. I remember him talking about meetings coming up to demo Zip2. Also, I remembered how beautiful Palo Alto was after having spent the last three school years in Philadelphia. And look at that Southern California tan he has! I remember thinking that California definitely agreed with Elon. He still had his beat-up BMW from his Philly days."Read moreCourtesy of Jennifer Gwynne / RR Auction
A picture of Elon Musk taken by Jennifer Gwynne at Musk's brother's student college house at Queen's University in Kingston, Ontario.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "Elon at my desk in my dorm room — no funny stuff this time, serious schoolwork time. Timeline note here — Elon talked about electric cars being the way of the future back in 1994. He said was going to be at forefront of the movement and I never doubted that he would be there — he was so matter-of-fact and so sure that electric cars were coming. So, honestly, for the last 25 years, I knew Telsa was going to work, that it was going to be successful. There is something so very infectious about Elon’s confidence and clarity."Read moreCourtesy of Jennifer Gwynne / RR Auction
Elon Musk, second from right, and Jennifer Gwynne, far right, are pictured with four other resident advisors before an end-of-the-year formal at the University of Pennsylvania in 1995.Read moreCourtesy of Jennifer Gwynne / RR Auction
A photo taken by Jennifer Gwynne of Elon Musk dressed in a tuxedo for an end-of-the-year formal at the University of Pennsylvania during his senior year.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "Elon being silly in my dorm room in the Quad. I remember thinking that it was so good to know he had a silly side that he would let me see."Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "On the way back from Canada during the 1994 holidays, we made a quick stop at Niagara Falls. I think we were very illegally parked so we just jumped out and took a picture."Read moreCourtesy of Jennifer Gwynne / RR Auction
According to RR Auction's website, this photo from Jennifer Gwynne is of "Elon Musk as a 23-year-old senior at the University of Pennsylvania, seated in a Philadelphia restaurant during a Resident Advisors team dinner in 1995."Read moreCourtesy of Jennifer Gwynne / RR Auction
From left to right: Jennifer Gwynne, Elon Musk, and Maye Musk are pictured during a trip to New York City in 1995.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website: "At the end of the 1994-1995 school year, before I headed to London for my study abroad program, Elon’s mother (Maye Musk) came to visit us in Philly. She took this picture of us on a bench in the lower portion of the Quadrangle — the big freshman dorm at the University of Pennsylvania. I must have received this print from Maye as her camera put the ‘old school’ orange date stamp in the corner. As I remember, the three of us were planning to drive to NYC to see the musical ‘Tommy’ — the whole trip was a lovely gift from Maye — but as we were getting ready to leave, something on Elon’s car broke. So we ended up spending five or so hours at an auto parts store so Elon could fix the issue himself. He did. We made it to NYC and had a wonderful time. I really like this picture - Maye had us pose a couple of different ways to get the ‘perfect shot’ — she knows how to make a camera work being a professional model."Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on the RR Auction website: "Over Christmas break of 1994, Elon invited me up to Canada to meet his family and spend the holidays with them. Our first stop was to visit his brother, Kimbal, who was studying at Queen’s University in Kingston, Ontario, Canada. Elon had studied at Queen’s University before transferring to Penn in Philadelphia. After Queen’s University, we headed to his mom’s (Maye Musk) lovely apartment in Toronto. This picture was taken at Kimbal’s student college house that he shared with several other guys. Oh, this place was so nasty college gross; looked like it had never been cleaned and all the guys had padlocks on their door when they were out. We were having drinks before heading out to a formal holiday party. I was initially nervous because I didn’t have anything to wear. But Kimbal’s female friends were very kind and lent me a dress."Read moreCourtesy of Jennifer Gwynne / RR Auction
A wide shot of the emerald necklace Elon Musk gave to Jennifer Gwynne during her trip to Toronto to meet his family.Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on the RR Auction website: "When we went to visit Elon’s mother in Toronto during the Christmas break of 1994, Elon gave me both the small ‘love, love, love’ note and the necklace. His mom had a number of these necklaces in a case in her bedroom and Elon told me they were from his father’s emerald mine in South Africa — he pulled one from the case. And because I had not gotten him anything as a Christmas gift (and I felt very guilty about that), he said we would consider the necklace an early birthday present for me. I wore the necklace for a number of years on and off, but it’s mostly been in my jewelry box for the last 10 years (always reminding me of Elon, of course)."Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on the RR Auction site: "This picture is of another Penn student who met up with us in Canada over the 1994 Christmas holiday. I don’t remember his name, but he was a Chinese national, and Elon shared some engineering classes with him. Elon was very fond of him."Read moreCourtesy of Jennifer Gwynne / RR Auction
A photo of Elon Musk in his BMW. According to a quote from Jennifer Gwynne on the RR Auction site: "Elon driving his BMW on the streets of Philadelphia. We were heading out to see Pulp Fiction on one of our first dates off campus. We had to sit in the front row it was so crowded — a very weird movie to see (up close) with a new beau."Read moreCourtesy of Jennifer Gwynne / RR Auction
The front of the signed card Elon Musk gave to Jennifer Gwynne in 1994.Read moreCourtesy of Jennifer Gwynne / RR Auction
A note Elon Musk wrote in a card to his then-girlfriend, Jennifer Gwynne. Gwynne said "Boo-Boo" was the nickname Musk gave her “after I needled him for not calling me something sweet.”Read moreCourtesy of Jennifer Gwynne / RR Auction
According to a quote from Jennifer Gwynne on RR Auction's website, this photo of Elon Musk was "From my post-London study abroad visit to San Francisco in the summer of 1995…Things for us weren’t going very well during this visit. Elon was not very good at a long-distance relationship. Talking on the phone seemed like a waste of time to him — NOT what a 20-year-old woman wants to hear."Read moreCourtesy of Jennifer Gwynne / RR Auction
Gwynne, who graduated from Penn in 1996 with a degree in English literature, said Musk, who dual majored in physics and economics, was intense and focused on the future when they dated.
“He talked about electric cars, he talked about alternate fuel sources. It was inspiring,” she said. “Penn is full of very smart people but there was something singular about his passion.”
Every once in a while, though, she could see a “boy-like nature” in him.
“He was just a goof from time to time,” she said. “He wasn’t very affectionate out in public, but he was all for quiet cuddles and hanging out together.”
Over the holidays in 1994, the two traveled to Canada, where Gwynne met Musk’s brother at Queen’s College in Kingston, and his mother, Maye, at her apartment in Toronto.
“Though we have wildly different backgrounds, I found Elon’s connection with his family and the support of his mom was something that attracted me to him,” she said. “Elon is a force in and of himself, but I know he gets a lot of that from Maye.”
During the visit, Musk brought Gwynne into his mother’s bedroom, where she had “a bunch” of emerald necklaces which he told her were from his father’s emerald mine in South Africa. He gave Gwynne one as a gift.
“Talk about a crazy story,” she said. “It’s one of my core memories.”
After Musk graduated from Penn in 1995, he moved to California, but the two kept in touch during Gwynne’s summer abroad in London that year. When she returned, she visited Musk in Palo Alto, where he was living in a second-floor apartment and going to pitch meetings.
“I went to see him as he was literally starting everything at that point,” she said. “It was an interesting moment in his life.”
But after Gwynne came back to Philly for her senior year, their long-distance relationship ended because Musk didn’t like talking on the phone. She hasn’t spoken to him since.
Gwynne, who married in 2020, said her husband is “really cool” with her having a famous ex.
As of Thursday, the highest bids in the online auction, which runs until Sept. 14, include $5,643 for the signed card and $3,384 for the emerald necklace. Some of the photos have bids of several hundred dollars each, including a goofy picture of Musk upside down, which has a high bid of $520.
Livingston is pleased with bidding so far but said he expects it to get “quite higher” as the auction nears its end.
Gwynne said she didn’t keep any mementos of her time with Musk for herself; everything she had is up for sale.
“This is all I got. This and my memories,” she said. “And I really do have fond memories.”
I'm a Features columnist who writes about what makes Philly weird, wild, and wonderfully unique. I also fight for Philly's honor against all of its haters.