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."
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. This picture was taken at [his brother] Kimbal’s student college house. 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."

Breakups are hard. Especially when your ex ends up becoming one of the most rich and powerful men in the world. But at least then you can sell off his old things for a profit, as Elon Musk’s former girlfriend is doing now. 

Jennifer Gwynne, who dated the now Tesla CEO while they were students at the University of Pennsylvania between 1994 and 1995, is selling personal items in an online sale at the Boston-based RR Auction, which is open now through tomorrow.

For the taking are 18 photographs, a signed birthday card, and a gold necklace that Musk gave to Gwynne. The necklace, which is currently bid at $8,800, may be of special interest to those who know a little about Musk’s family history, because it contains an emerald from the Zambian mine owned by Errol Musk, Elon’s father who made the family’s wealth as a South African property developer and miner. 

The top price as of Tuesday afternoon is for a birthday card addressed to Gwynne, “aka Boo-Boo,” and signed “Love, Elon.” It currently has 24 bids, topping out at $12,000.

A screenshot of an Elon Musk photo, part of a batch of mementos that his ex-girlfriend has placed on auction.Source: RR Auction

According to Gwynne, some of the photos were taken during the couple’s trip to Canada to meet his family, who were then living in Toronto, and pictures from a trip to Rhode Island, where they visited Gwynne’s family in 1994. 

In other photos, a twentysomething Musk appears cuddling with Gynne, standing at Niagara Falls, and hanging out with friends in a dormitory. The highest-priced is a photo of Musk slouched at a computer in a messy room, with a bottle of lotion and laundry detergent on the desk, currently bid at $2,900.

A screenshot of an Elon Musk photo, part of a batch of mementos that his ex-girlfriend has placed on auction.Source: RR Auction

Gwynne told the TV show Inside Edition that she decided to sell the items in order to raise money for her step-son’s college tuition. She had seen headlines of another auction at RR that sold an old assignment graded by Elon while he was a teaching assistant for more than $7,000.

RR has a history of technology-themed sales, having also sold Steve Jobs’s first Apple-1 prototype in August for almost $680,000.

Pehaps a nugget of Carrie Bradshaw wisdom is useful to consider: “Maybe the past is like an anchor holding us back.” 

For Gywnne, maybe that anchor just need to be sold to the highest bidder.