Elon Musk’s ex on his ambition, romantic past and why he can’t settle down: ‘His certainty does not translate’

Elon Musk knew where he was headed in business but was useless at maintaining long-distance love, Jennifer Gwynne tells Meredith Clark

(RR Auctions)

For Jennifer Gwynne – who dated Elon Musk in 1994 – her relationship with the world’s richest man was short but sweet, and full of mementos she’s kept in storage until today. Now, Gwynne is auctioning off old photos and items she was gifted from the future billionaire, mainly because she feels it was just about time.

Jennifer Gwynne, now 48 years old and living with her family in South Carolina, met Elon Musk when they were both resident advisors in the same freshman dorm at University of Pennsylvania. Speaking to The Independent, Gwynne recalls how the two hit it off instantly.

“He definitely started off shy and quiet, which was my type,” she said. “He just won me over by bringing me food one night to my room. And we were an item after that.”

Elon Musk was just like any other college student, but his dreams of electric cars and living on Mars were just as present as they are today. Even 28 years ago, Gwynne believed that Musk would become a successful innovator.

“He was definitely younger, maybe a little less world-weary. Definitely brilliant and a visionary,” she revealed. “I mean, he talked about electric cars and solar power even way back then, but he just had a kind innocent ‘this is how the world is going to change’ view about it.”

During their year-long relationship, much of Musk’s focus remained on the growing technology industry in Silicon Valley, and “he knew that’s where he was going,” according to Gwynne.

After he graduated from UPenn in 1995 with a degree in physics and economics, moving out to California was exactly what he did. Although, it came at a cost to his relationship with Gwynne. While Musk was living in Palo Alto, Gwynne was studying abroad for a summer in London. She still had her senior year of college to complete, and long-distance proved to be a challenge for Musk.

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“I was like, ‘We need to talk on the phone more if this long-distance thing’s going to work,’” Gwynne recalled. “And he was like, ‘I don’t like talking on the phone. It’s a waste of time.’”

The two called off their relationship that year, but as Musk’s fame continued to grow, so did the amount of attention placed on his love life. In 2000, Musk married his first wife, Canadian author Justine Wilson.

Musk met Wilson while they were students at Queen’s University in Ontario, Canada, before he transferred to UPenn. The two went on to welcome six children, one of whom died from Sudden Infant Death Syndrome at 10 weeks old. In 2008, Musk filed for divorce and was engaged to British actress Talulah Riley six months later.

Riley, who played Mary Bennet in the 2005 adaptation of Pride and Prejudice, was married to Musk twice – first from 2010 to 2012, and again from 2013 to 2016. The two never had children together. The same year he ended his relationship with Riley, Musk began dating Amber Heard shortly after her divorce from Johnny Depp. But after their split in February 2018, he moved on to Canadian singer Grimes – whose real name is Claire Boucher.

In May 2020, Grimes gave birth to her first child with Musk – a son named X AE A-XII. In September 2021, Musk revealed to Page Six that he and Grimes have “semi-separated” due to conflicting schedules and locations. That’s why it came as such a surprise to fans when the pair welcomed a second child together in December 2021 – a daughter named Exa Dark Sideræl Musk via surrogate.

Most recently, Musk fathered a set of twins with 36-year-old Neuralink executive Shivon Zilis in November 2021, weeks before the billionaire welcomed his second child with Grimes.

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Although the Gwynne and Musk went their separate ways, she has still held onto some of the precious keepsakes from their year-long relationship. She first had the idea to put some of the items up for auction when a fellow UPenn classmate received $7,700 from an exam paper Musk had graded with his initials, back when he was a teaching assistant.

“I ran down the stairs when I saw that article and said to my husband, ‘I have a note from Elon and it probably says something sexier than his initials,’” she explained. With Musk’s controversial business deals and personal antics both making headlines, Gwynne figured it was time to let go of their relationship souvenirs that were collecting dust.

Eighteen photographs of Musk are currently available to purchase on RR Auctions until 14 September. Some of the pictures feature a young Musk photographed solo, or with friends and Gwynne. The minimum bid for each photo is $100. Among the big ticket items includes a signed birthday card from Musk, currently priced at $2,892 with ten bids. The card reads: “Happy Birthday Jennifer (aka, Boo-Boo) Love, Elon”.

There is also a one dollar bill signed by the Tesla boss available for auction, which sits at $2,420 with 15 bids. But one of the more difficult items for Gwynne to part with is a 14k gold necklace containing a small green emerald, which she claims was from Musk’s father’s emerald mine in South Africa.

“[Elon’s] not very sentimental and emotional, and so when he made that very romantic gesture, it meant a lot to me because he was opening himself up,” she said.

(Jennifer Gwynne)

Included with the necklace are two original photos of Musk and Gwynne, one showing them standing with Musk’s mother, Maye, during a visit to New York City. Gwynne described when she first met Musk’s mother Toronto during Christmas break in 1994.

“[Maye] was very sweet, very gracious. She knew Elon thought a lot of me, so she just asked my opinion on things, always included me in conversations,” Gwynne said.

As for the auction, Gwynne hopes the signed birthday card sells for its estimated $10,000, mainly because a portion of the funds will be donated to CARE, an animal rescue organisation in Lexington, South Carolina. The remaining funds will be used to help pay for her 13-year-old stepson’s college tuition.

While Jennifer Gwynne and Elon Musk haven’t spoken since they parted ways in 1995, and have gone on to marry different people – or in Musk’s case, two people with at least ten children across three women – she still has some words of wisdom for the man she knew 28 years ago.

“Elon’s certainty when it comes to business and technology and large, grandiose plans does not translate well to relationships,” Gwynne said. “I know he doesn’t need my input, but I think he needs to bend a little bit because if he’s going to find that partner that he’s obviously looking for, he’s going to have to give in and not always be in charge.”