Inside Sasha Obama's Private Post-White House World

Malia Obama & Sasha Obama Make Rare Appearance Together in Party Photo

Sasha Obama was 7 years old when she moved into the White House.

So no wonder the Internet is still prone to losing its mind when the now 23-year-old shows off her midriff.

Though Sasha and sister Malia Obama, 26, grew up in the public eye, not exactly hidden away from media attention despite their parents' solid efforts to keep their daughters out of the fray—"That was a lot of work," mom Michelle Obama recently acknowledged—it was startling to see two little kids move into 1600 Pennsylvania Ave. and watch two young women move out.

"What I tell them is...that they have to walk their own walk," the former first lady told Oprah Winfrey during a stop on Oprah's 2020 Vision: Your Life in Focus tour, asked if there was a "running theme" in the advice she gave her children.

Like any mom and dad, former President Barack Obama and his wife might quibble with the idea of their daughters being all grown-up no matter how old they are, but so far the Obama sisters have been busy making their parents proud at every stage of the game.

When the two-term Obama presidency ended in January 2017, Malia was in the middle of the gap year she took before enrolling at Harvard University, but Sasha—the youngest first child to move into the White House since a 2-month-old John F. Kennedy Jr.—was still some months shy of her 16th birthday and had a couple years of high school left to go, the main reason why the family remained in Washington, D.C.

The Obamas rented an 8,200-square-foot home in the Kalorama neighborhood, near Dupont Circle, and went all out with a party for Sasha that May—a VIP-only event, but not so much that pictures of the birthday girl in a red Jill Jill Stuart slip dress didn't make the rounds.

Go ahead and blame the physical inability of teenagers not to post on social media, as further evidenced by a 2020 TikTok featuring Sasha and a friend lip-syncing to Moneybagg Yo's "Said Sum" remix featuring City Girls that was quickly deleted—but not until after a proud tweet from rapper JT sent it whizzing virally around the world.

"Every weekend was hard following these little girls around," Michelle told Oprah in February 2020. "We had to worry about what parties they were going to, whether there was alcohol, I had to know who the parents were, so every weekend for me was hard."

That was toward the end of their time there, though. When they first got to the White House, the first lady wondered how she was going to make their new palatial residence, complete with tuxedo-wearing butlers, many of them Black and Latino men, feel like home.

"We had to change the dress code," Michelle told Stephen Colbert during the final stop on her 34-city Becoming book tour, explaining how she didn't want Malia and Sasha—or their friends—to get the impression that having liveried black servants was something normal to see in life. "You can't walk around every day in a tuxedo. Girls would have pool parties and play dates and little kids over, and it's like, that doesn't even look right to me. And I had to beg the housekeepers, 'these girls have to learn how to clean their own rooms and make their beds, and do their laundry. You cannot do this every day, 'cause they will not live here forever—and I am not raising kids that don't know how to make a bed.'"

When the family acquired Bo and Sunny, their Portuguese water dogs, helping to care for the first pets was added to the girls' list of responsibilities.

Sasha graduated from Sidwell Friends School (alumni include Malia, Chelsea Clinton and Al Gore III) in 2019. After a summer that included a family vacation to the South of France, she packed up to attend the University of Michigan.

"I think it's cool that even though her family went to Ivy League schools, she decided that UM was the caliber high enough to match that of an Ivy League school," Jessica Brinser, then a Michigan sophomore, told the Detroit News in August 2019 about her notable new fellow Wolverine after move-in day. She added, "We hope she finds her fit here just like we all have. We all love it here. We hope she does, too."

Sasha's parents helped move her into her dorm, just as they hauled crates and bedding for Malia when they dropped her off at Harvard in 2017.

And, once again, there were some tears.

"We were really good about it," Michelle said in December 2019, recalling that emotional day to Jenna Bush Hager on Today. "We didn't want to embarrass her because she had roommates and it was at the end, after lunch, when we said that final goodbye."

"When we got into a car, me, Barack and Malia, who was there with us, and then Sasha drove off on her own and said that last goodbye. That's when we were like [she mimicked sobbing noises]."

Jenna and her sister, Barbara, wrote a letter of congratulations and encouragement to Malia and Sasha in 2017 about joining the club of "former First Children."

"Enjoy college," the twins advised. "As most of the world knows, we did. And you won't have the weight of the world on your young shoulders anymore. Explore your passions. Learn who you are. Make mistakes—you are allowed to. Continue to surround yourself with loyal friends who know you, adore you and will fiercely protect you. Those who judge you don't love you, and their voices shouldn't hold weight. Rather, it's your own hearts that matter."

Sasha actually ended up transferring to University of Southern California for her senior year to be closer to Malia, who moved to Los Angeles to pursue her writing and directing aspirations. And that's where Sasha graduated from in 2023 with a degree in sociology.

Still, mark some of the other ceremony attendees down as surprised when "Natasha Obama" showed up in USC's Dornsife College of Letters, Arts and Sciences graduation program and they found themselves seated near the former president and first lady.

"They have grown up right before our very eyes and they're doing well," Michelle told Ellen DeGeneres in 2022, noting that both of her L.A.-based girls had "boyfriends and real lives."

"They cannot define themselves by looking at each other or looking at me or their dad," Michelle told Oprah in 2020, explaining the gist of what she and Barack have told their daughters about forging their own paths in the world. "They have to take the time to get to know themselves—give themselves a moment to figure out who they want to be in the world, not who they think I want them to be, not what the rest of the world says about them, but to really think about how they want to shape their lives and how they want to move in this world.

"So, I don't want them measuring themselves by external influences, and for young girls, that is hard to do." 

As she said on Today, "I'm excited for my girls to grow up and to become independent." Even though, she added, "You feel a little melancholy that they will never be the little ones that sit on your lap and listen to your every word and look at you adoringly. Those days are over."

But as a recent pic of Malia and Sasha hanging out together proves, they've still got each other.

See Malia and Sasha's road from their White House childhood to their L.A. adulthood in photos: