A few years after Barack Obama famously said Drake could “do anything he wants,” the rapper was spotted partying in Los Angeles alongside two familiar faces: Malia and Sasha Obama. The former first daughters, now fully embracing adulthood, were photographed enjoying a night out at a Hollywood hotspot—far from the formal world they grew up in. Malia, born in 1998, and Sasha, born in 2001, spent eight formative years in the White House.

Michelle Obama has often spoken about the pressure they endured under constant public attention, explaining that her daughters learned early how to stay poised while building their own identities. “They had to learn how to balance unwanted attention, but still be polite,” she said. Despite the structure around them, she emphasized independence: “You’re not going to live here forever.”

Their father also felt the shift as they grew older, recalling the moment he saw Malia dressed for prom: “She’s lovely. She’s beautiful.” After graduating high school, Malia attended Harvard and later pursued filmmaking, debuting her short film Heart at Sundance in 2024. Sasha completed her sociology degree at USC in 2023. The sisters now share a home in Los Angeles, a fact Michelle says gives her “comfort.”

Part of their L.A. lifestyle includes nightlife. Recently, they were seen at The Bird Streets Club with Drake, who is touring nearby. Sasha sported a cropped black corset with cargo pants, while Malia wore a sheer lace-up top and printed trousers. Reports say they stayed until about 4 a.m. before leaving with friends. Drake’s connection to the Obamas goes back years, and the sight of them together sparked lively conversation online—proof that the sisters continue to attract attention as they carve out their own lives.