Malia and Sasha Obama party with rapper Drake

Malia, born on July 4, 1998, and Sasha, born on June 10, 2001, spent eight formative years within the confines of the White House. They arrived at 1600 Pennsylvania Avenue as children and departed as young women, navigating the pressures, scrutiny, and intense public interest.

Michelle Obama has frequently discussed the balancing act her daughters had to master from an early age. In a discussion with Melinda French Gates on the Moments That Make Us podcast, she stated, “They are observed. They had to learn how to manage the unwanted attention, but do so graciously… to create their own lives in the public eye and not be overwhelmed by it.” She emphasized that despite the support they received—including staff, schedules, and structure—she raised them to be self-sufficient: “You’re not going to live here, and with me, forever.”

For Barack Obama, a particular moment in 2014 brought that reality into sharp focus—Malia getting ready for her prom. “The first time you see your daughter in heels is somewhat startling,” he confessed on Live with Kelly & Michael. “She’s lovely. She’s beautiful.”

After completing high school in 2016, Malia took a gap year before enrolling at Harvard, where she graduated in 2021. She utilized her time off to pursue her creative aspirations, working on productions such as Extant and eventually joining the writing team for Amazon’s Swarm. In 2024, under the name Malia Ann, she premiered her short film Heart at the Sundance Film Festival—marking her first significant step as a writer-director.

Sasha, referred to by her father as “the comedian in the family,” has successfully completed her academic journey. She commenced her college education at the University of Michigan during the pandemic and subsequently transferred to USC, where she earned a degree in sociology in 2023.

Currently, the sisters reside together in Los Angeles. Michelle Obama has expressed that knowing they are close provides her with great comfort: “It feels good to know that the two girls you raised find solace at a kitchen table with one another.”

Part of their shared lifestyle includes enjoying the nightlife. Recently, Malia and Sasha were spotted celebrating at The Bird Streets Club alongside Drake, who is currently on tour with his show “It’s All A Blur—Big As The What?” at the nearby Crypto.com Arena.

Both women showcased striking, evening-appropriate outfits. Sasha donned a cropped black corset that revealed her midriff, which she paired with loose cargo pants and open-toe shoes, her braids styled in a high ponytail and her jewelry sparkling under the club’s lights. Malia chose a sheer lace-up top and high-waisted printed trousers that accentuated her figure, completing her ensemble with chunky boots and her long brown hair cascading freely.

Reports indicate that they remained at the venue until approximately 4 a.m. before departing with friends—two young women embarking on their own Californian chapter, far removed from the strict formalities of Washington.

Drake’s association with the Obamas dates back several years. In 2010, he expressed a desire to portray Barack in a future biopic, stating, “I could play him.” The former president later responded in 2020 with warmth and a touch of humor: “Drake seems to be able to do anything he wants… If the time comes and he’s ready…” He also mentioned that his daughters “would be just fine with it.”

The images from their outing in Los Angeles ignited considerable discussion online, not only regarding their friendship with the musician but also about how fully the Obama daughters have matured into their own lives—independent, fashionable, and navigating adulthood on their own terms.

What are your thoughts regarding their evening out? Please feel free to express your opinions and share this narrative—everyone seems to have a viewpoint concerning the Obamas, Drake, and a weekend in Hollywood.