Bill Gates' youngest daughter Phoebe rekindles romance with high school sweetheart after split from Paul McCartney’s grandson

On Monday, Phoebe shared a photo on Instagram posing alongside Chaz, with one hand wrapped around him and the other resting on his chest. Both are dressed in matching black and white outfits, with Phoebe in a strapless, body-hugging evening gown and Chaz in a suit and tie.

Phoebe captioned the post with a heart emoji, and a comment from an alleged family member of Flynn’s reads, "Been waiting for this one. Love you guys!!"

The couple is believed to have first dated in 2019 when both attended the prestigious Lakeside High School in Seattle, though the exact timing of their split remains unclear, according to the Daily Mail.

Bill Gates' daughter Phoebe Gates poses for a photo with high school sweetheart Chaz Flynn. Photo courtesy of Phoebe's Instagram

Before reconnecting with Chaz, Phoebe had been in a relationship with Paul McCartney's grandson, Arthur Donald, for two years. Arthur is the son of British photographer Mary McCartney and her ex-husband Alistair Donald.

Phoebe and Arthur’s relationship came to light in October 2023 when she posted a photo of them together in Paris. Later, the billionaire heiress confirmed their relationship in a blog post for Nylon magazine, calling Arthur her "boyfriend" after her graduation from Stanford University. The couple was also seen together with Phoebe’s mother, Melinda French Gates, at a 2024 event in New York. It remains unclear whether Arthur ever met Phoebe’s father, Bill.

In September, Phoebe, 23, discussed her new relationship on "The Burnouts" podcast, which she co-hosts with business partner Sophia Kianni. She shared, "It’s amazing. It’s the best thing ever."