Years after former President Barack Obama jokingly suggested that Drake could achieve anything, his daughters, Malia and Sasha Obama, were spotted enjoying a night out with the Canadian rapper at The Bird Streets Club in Los Angeles. The former first daughters, now adults, were seen dressed in chic outfits suitable for the trendy Hollywood hotspot. Sasha wore a black cropped corset paired with low-slung cargo pants, while Malia opted for a sheer lace-up top and high-waisted printed trousers. The two reportedly partied with Drake and his friends into the early hours of the morning before leaving together.

Having spent their childhood under constant public scrutiny during their time in the White House, Malia and Sasha faced unique challenges in balancing a normal teenage life with the relentless attention of the media. Their mother, former First Lady Michelle Obama, has spoken about how she and Barack worked to raise their daughters to be independent and confident, preparing them for life beyond the White House’s protective walls. Malia, born in 1998, graduated from Harvard University in 2021 after a gap year where she gained industry experience as a production assistant and writer. Sasha, born in 2001, graduated from the University of Southern California in 2023 with a degree in sociology, and the sisters now share a home in Los Angeles.

The outing with Drake marks a clear sign of the sisters’ transition into adulthood and their embrace of a more independent social life. Michelle Obama has previously shared her relief in knowing that her daughters enjoy quiet moments together, like finding comfort at a kitchen table, and it appears they also find joy in more lively social scenes. The photos from their night out with Drake offer a rare, candid look at the Obama sisters enjoying their newfound independence in the vibrant setting of Los Angeles.

Drake, who has long admired Barack Obama, has also publicly expressed interest in playing the former president in a biopic. In 2020, Obama humorously endorsed the idea, acknowledging Drake’s multifaceted talent and, more importantly, noting that his daughters would likely be “just fine with it.” This playful connection between the rapper and the Obama family adds an interesting layer to the recent night out, showcasing their mutual respect and admiration for one another.

The sighting of Malia and Sasha Obama with Drake in Hollywood highlights their ongoing journey into adulthood and the freedom they now have to explore their social lives without the constraints of their time in the White House. Their stylish appearances and late-night revelry with such a prominent figure reflect their emergence as independent, confident young women, all while their parents’ supportive presence continues to subtly influence their path.