Elon Musk’s first girlfriend is auctioning off photos of them as lovestruck, 𝑏𝑎𝑏𝑦-faced college juniors and revealing the secrets of their sweet romance.
Jennifer Gwynne dated the Tesla billionaire when they were both in their early 20s and studying at UPenn.
The pair were together for one year, during which time she visited his model mother Maye, met his siblings and heard all about his plans for electric cars. Now, she is married with a stepson and living in South Carolina. After watching him dominate headlines and seeing others cash in on his fame, she is now selling some of the keepsakes from their love affair with the hope that the proceeds will help pay for her stepson’s college tuition.
Speaking to DailyMail.com on Monday, Gwynne, now 48, said their romance was a ‘sweet’ one but was lacking in affection or ‘PDA’ – because Elon largely resisted both.
They broke up when he moved to Palo Alto in 1995, around the same time he became serious with his first wife, Justine, whom he’d also been seeing behind her back, she says.
Elon Musk is shown in his early twenties in a photograph with his ex-girlfriend, Jennifer Gwynne, and one of their college friends. She is now selling photos and mementos from their year-long fling via auction
Love’s young dream: Elon and Jennifer together in 1994. She said he only ever wanted someone to ‘be with him’ and ‘support him’
‘He was very intense… very focused. Even back then, he was talking about electric cars,’ Jennifer says today of her famous first love
Jennifer said that while Elon ‘wasn’t affectionate’, he made sure you know if he was courting you
The biggest ticket item is a 𝐛𝐢𝐫𝐭𝐡day card which he wrote to her in December of 1995. It reads: ‘Happy 𝐛𝐢𝐫𝐭𝐡day Jennifer (aka Boo Boo). Love, Elon.’ ‘Boo boo’, she says, was his way of poking fun at her. She had complained to him that he wasn’t affectionate enough towards her before he wrote it. ‘He thought nicknames were foolish… I teased him about it, I’d say “be a bit more sweet”. ‘He did it to be more romantic, because I had told him to,’ she said. Right, Elon bought Jennifer this necklace in December 1995, while they were visiting his mother in Toronto. It was supposed to be a Christmas gift, but they decided it would be for her 𝐛𝐢𝐫𝐭𝐡day instead, she tells DailyMail.com
‘His shy nature attracted me at first… he used to be my type,’ Gwynne said.
Then a budding entrepreneur bursting with ambition and ideas, she said she ‘always knew’ he would ‘go places’.
‘He was very intense, very focused on his studies. Back then he was always talking about electric cars… he was definitely going somewhere. He just saw school as a stepping stone.’
The photos show the pair on road trips, drinking champagne and hanging out with friends.
In some, Elon appears hunched over an early computer. In others, he is dressed in black tie for formal college events.
Out on the town and dressing down: A young Elon Musk dressed for a black tie event and right, with some Minute Maid OJ
‘We were physical when we needed to be… but there wasn’t any hand-holding or anything like that,’ she says
While he resisted ‘PDA’, Gwynne reveals that he won her over with a Chinese take-out from a local, off-campus restaurant called Beijing.
‘When he is courting you, you know he is interested, but he wasn’t extremely affectionate.
‘We were physical when we needed to be… but there wasn’t any hand-holding or anything like that. He liked to be together. He just liked having someone there with him, someone to support him.’
She describes visiting his mother Maye – a ‘wonderful and stunning woman’ – when she lived in Toronto, and also meeting Elon’s siblings Kimbal and Tosca.
‘[Maye] was wonderful, very sweet, very gracious and really included me in conversations. She was wonderful.
‘She came to Philadelphia at the end of the school year and she took us to New York to see Tommy on Broadway.’
She never met his father, Errol, but remembers Elon telling her they didn’t ‘get along’.
Elon was ‘always going places’, says Jennifer, who said he seemed to view school as a ‘stepping stone’ for where he really wanted to be
After leaving UPenn in 1995, Musk attended Stanford – but only for two days. He is shown before making the move, while still on the East Coast
Musk with one of the group’s college friends. Jennifer talks fondly of their road trips and times ‘hanging out’ in their dorm
The couple in May, 1995, not long before he moved to California and the romance came to an end
Musk with friends at dinner as a 𝑏𝑎𝑏𝑦-faced college student
Eyes on the prize: Musk, sitting next to a computer, surrounded with clothes, a bottle of Eucerin and what appears to be laundry detergent
‘Back then I know he was remarried and had recently had a daughter… he’s got a whole thing with his family.
‘I saw a picture of Elon holding a stepsister and he just said they didn’t get along.’
At the time of her romance with Musk, his father was married to second wife Heide Bezuidenhout.
She had a four-year-old daughter Jana when they wed. After Errol and Heide’s divorce in 1997, Errol and Jana controversially got together. They have since had two babies of their own.
Gwynne says that she and Elon split when he moved to California to pursue his tech dreams.
Elon during some of the couple’s outings and road trips. The romance ended when he moved to California because he didn’t want to do long distance, Gwynne said
Elon, joking around with friends while at UPenn in the early 1990s
Unbeknownst to her, he was also dating his first wife, Justine.
‘Over the years I realized… it was clear he was looking for a wife. The perfect wife.
‘He’s got a type. I was very blonde, I fit the type,’ she said.
She visited him once after he moved to California, and that was when he called it quits.
‘If we weren’t physically together it was a problem because he’s not good on the phone. He said, “it’s a waste of time.”
‘It was hard, it was not what a 20-year-old woman wanted to hear. I was totally in love with him,’ she says today.
Gwynne says that while they have not spoken for decades, she doesn’t believe her old boyfriend to be ‘happy’ in his life now.
‘I don’t agree with a lot of what he says now. Don’t get me wrong, he is brilliant – a once in a multigenerational mind… I just think honestly he’s looking for love or some kind of validation.
‘I’m sure he doesn’t care what I have to say I just wish he was a bit happier. He seems to be trying to find something. I’m very happy with my life and I don’t know if he can say the same.’
She decided to sell the photos and necklace that he gave her as a Christmas gift with the hope of raising money to put towards her stepson’s college fund.
Gwynne had resisted for years, but says after seeing others make thousands from selling their Elon-touched treasures, ‘now’s the time’.
Now 48, Jennifer say she believes Elon is ‘searching for something’. ‘Don’t get me wrong, he is brilliant – a once in a multigenerational mind… I just think honestly he’s looking for love or some kind of validation. ‘I’m sure he doesn’t care what I have to say I just wish he was a bit happier. He seems to be trying to find something. I’m very happy with my life and I don’t know if he can say the same’
‘I’ve had these pictures and the notes for a long, long time. But now I’m like, “well the man cannot stay out of the headlines… so…”.
The biggest ticket item is a 𝐛𝐢𝐫𝐭𝐡day card which he wrote to her in December of 1995.
It reads: ‘Happy 𝐛𝐢𝐫𝐭𝐡day Jennifer (aka Boo Boo). Love, Elon.’
‘Boo boo’, she says, was his way of poking fun at her. She had complained to him that he wasn’t affectionate enough towards her before he wrote it.
‘He thought nicknames were foolish… I teased him about it, I’d say “be a bit more sweet”.
‘He did it to be more romantic, because I had told him to,’ she said.
The auction is now live on RR Auction and will take bids until September 14th.
Elon married first wife Justine in 2000 and the pair quickly started a family. Their first 𝘤𝘩𝘪𝘭𝘥, Nevada, died tragically of Sudden Infant Death Syndrome in 2002.
Elon and Justine divorced in 2008. He then married British actress Talulah Riley twice – once in 2010 and then again in 2013 (the pair split in 2012 and reconciled the following year).
Their second divorce came in 2016. He went on to have a brief romance with Amber Heard, then settled down with Grimes. They had two 𝘤𝘩𝘪𝘭𝘥ren together (the first, X Æ A-Xii Musk, in 2020 and the second, Exa Dark Sideræl in November last year via a surrogate).
Around the same time, he welcomed twins with Neurolink executive Shivon Zilis.
Now, he is believed to be dating Natasha Bassett. He recently denied a Wall Street Journal claim that he’d had an affair with Sergey Brin’s wife Nicole Shanahan, but joked he was trying to ease the ‘underpopulation crisis’ with his frequent philandering.
