Malia Obama and Sasha Obama were 10 and 7 years old when they moved into the White House.
And though they grew up in the public eye, hardly hidden away from either accepted or unwanted attention despite their parents’ solid efforts to keep their daughters out of the media fray, it was a little startling to see two little kids move in and watch two young women move out.
“What I tell them is…that they have to walk their own walk,” Michelle Obama told Oprah Winfrey in February 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 recent empty-nesters, former President Barack Obama and the first lady might quibble with the idea of them being fully grown up yet, but so far the Obama sisters have made their mom and dad proud every step of the way.
“That has been exhilarating, to watch the two little beings you were in charge of grow up,” Michelle reflected in the Netflix documentary Becoming, which touched on the highlights of her life and the inspiration she evoked on her 2018-19 book tour promoting her memoir of the same name.
“I’m excited for her to be proud of what she’s done, ’cause I think that’s the most important thing for a human to do, is to be proud of themselves,” Sasha said about her mom in the rarer-than-royalty interview that she and Malia did for the film.
“No longer facing that same scrutiny, being able to let all of that leave your mind,” Malia added, “creates so much more space.”
The same could be said for the sisters themselves.
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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. (Something about the physical inability of teenagers not to post on social media…)
But it’s not as if life for Sasha and Malia all of a sudden turned normal-normal once their dad was no longer president. A security detail is still a part of their daily lives, and the world remains both invested in their accomplishments, hopes and dreams and, on the flip side, happy to absorb any bit of juicy gossip—should Malia or Sasha ever provide any.
So far, anyone hoping for a scandal has been sorely disappointed. After all, it wasn’t just the Secret Service keeping a close watch on them during those eight formative years spent residing at 1600 Pennsylvania Avenue.
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“Every weekend was hard following these little girls around,” Michelle Obama told Winfrey in February. “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 Portuguese Water Dogs Bo and Sunny, helping to care for the first pets was added to the girls’ list of responsibilities.
Sasha, who’s celebrating her 19th birthday, graduated from Sidwell Friends School (alumni include her sister, Chelsea Clinton and Al Gore III) a year ago. 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 about her notable new fellow Wolverine last August 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.”
The 44th POTUS and first lady, aka Dad and Mom, helped move her into her dorm, just as they hauled crates and bedding for Malia when she moved into Harvard Yard in 2017.
And, once again, there were some tears.
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“We were really good about it,” Michelle Obama said in December, 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].”
Hager 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 maintained an active social life in high school and presumably continued to do so in college, but she didn’t rush a sorority (as far as anyone could suss out) and her classmates seem to be maintaining respect for her private life (and their own, because who wants to be the person who tattled on Sasha Obama?).
Like her big sister, the younger Obama daughter is a frequent recipient of texts from their mother.
“Did I ever tell you to remember things like are you eating some green things?” Michelle Obama gave an example of one of those nagging mom texts, er, helpful reminders to Oprah. “Gosh, I give them so much advice that they are sick of me.”
It’s funny, how an ability to fill arenas and theaters with fans hanging on her every word doesn’t necessarily carry all that much sway with one’s own kids.
Instagram / Michelle Obama
“I threaten them that I’m going to buy an apartment near their campus and visit and sit in their classes, but that’s an idle threat,” Michelle joked to Entertainment Tonight in May 2017. “I’m going to be happy to see them thriving on campus, work study jobs, traveling and having all these wonderful independent experiences that are going to make them phenomenal people.”
Now that the nest is empty, however, Michelle has said—in Becoming and in interviews—that she’s relishing the opportunity to rediscover her partner in life, Barack Obama (they added an estate on Martha’s Vineyard to their real estate portfolio last year), and focus on working with the next generation of young leaders.
As for her own daughters, she’s excited to watch their future unfold, though she says neither she nor their father want to factor too heavily into their decision-making process.
“They cannot define themselves by looking at each other or looking at me or their dad,” Michelle Obama said, 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.” The former first lady 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.”
