A few years after Barack Obama famously praised Drake as someone “able to do anything he wants,” the Canadian rapper was recently spotted in Los Angeles enjoying a night out with former first daughters Malia and Sasha Obama. The outing highlighted how much the sisters have grown since their time in the White House, showing them navigating adulthood under their own terms and away from the constant public scrutiny of their youth.
Malia, born in 1998, and Sasha, born in 2001, spent their formative years in the White House spotlight, arriving as children and leaving as young women well aware of the pressures and public attention that accompanied their family life. Michelle Obama has spoken extensively about raising them to balance scrutiny with independence, teaching them to handle visibility politely while still developing their own identities and ambitions.
Barack Obama reflected on the bittersweet milestones of their upbringing, such as seeing Malia in heels for the first time before her prom. After graduating high school in 2016, Malia took a gap year to explore her creative interests, later attending Harvard and graduating in 2021. She has since pursued a career in writing and directing, with her short film Heart premiering at the Sundance Film Festival in 2024.
Sasha, described by her father as the family’s comedian, followed her own academic path, starting college at the University of Michigan during the pandemic before transferring to USC, where she graduated with a sociology degree in 2023. The sisters now live together in Los Angeles, maintaining a close relationship that brings their mother, Michelle, great comfort, as they navigate young adulthood side by side.
Their recent night out at The Bird Streets Club in Los Angeles, in the company of Drake, showcased their stylish, confident independence. Sasha wore a cropped black corset with cargo pants and open-toe shoes, while Malia opted for a sheer lace-up top paired with printed trousers and chunky boots. The sisters stayed until the early hours, demonstrating a freedom and self-expression far removed from the formality of their White House years.
Drake’s longstanding connection with the Obamas, including his lighthearted interest in portraying Barack in a biopic, adds context to the evening, reflecting the bond the sisters have formed with him over the years. The outing sparked conversation about the sisters’ adulthood, highlighting their independence, style, and ability to navigate life in the public eye while fully embracing their own paths and personal identities.
