Sasha Obama, Malia Obama, Michelle Obama, and Barack Obama

Malia and Sasha Obama’s head-turning transformations have been astonishing to watch throughout their years in the spotlight.

Of course, the Obama sisters’ lives will never be "normal." After all, they spent their formative years living in the White House while their father, Barack Obama, served two consecutive terms as U.S. President. For Malia and Sasha, this meant going to school (and essentially everywhere else) with armed guards in tow, playing make believe surrounded by hundreds of years of American history, and eating family meals prepared by a full staff.

Still, the Obama sisters had an ace card — their mother, Michelle Obama — who ensured their childhood was as normal as possible during the eight years the family spent living at 1600 Pennsylvania Avenue. In the past, children of presidents have been the subject of tabloid gossip; however the Obamas were very strict about what was shared about their girls. Malia and Sasha were teenagers before the public knew anything about them, and both ladies have continued to retain an elegant distance from the media even upon entering college and becoming burgeoning style icons with their flawless fashion. Here’s a look at the head-turning transformations of Malia and Sasha Obama.

Malia and Sasha Obama were brought into the world by IVF

Sasha Obama, Malia Obama, Barack Obama

Malia and Sasha Obama are presidential children who grew up to be gorgeous inside and out, thanks to the determination of their mother, Michelle Obama.

Michelle detailed plenty of things fans never knew about Malia and Sasha in her memoir, Becoming – such as how she was ultimately forced to undergo IVF treatment in order to conceive both of her daughters (via the Associated Press)."We were trying to get pregnant and it wasn’t going well. We had one pregnancy test come back positive, which caused us both to forget every worry and swoon with joy, but a couple of weeks later I had a miscarriage, which left me physically uncomfortable and cratered any optimism we felt," she heartbreakingly recalled of her difficult path to motherhood.

With her husband working full time, Michelle was left to inject herself with hormones, which she wrote about using to "manipulate" her body into getting pregnant. Thankfully, the incredibly stressful process was successful — and Barack and Michelle Obama eventually saw their dreams of having a family of their own come to life.

Malia and Sasha Obama’s sleepovers required armed guards

Malia and Sasha Obama’s head-turning transformations were undoubtedly influenced by their time living in the White House — which, as one might imagine, offered many perks for the young sisters.

However, there were plenty of rules the presidential kids had to follow, as Michelle Obama told Gayle King during an interview at the 2019 Essence Festival (via CBS News). After all, the Obama sisters couldn’t attend normal activities for kids their age — such as sleepovers — without having intimidating Secret Service agents in tow.

As Michelle hilariously recalled to King, she would have to phone ahead to advise expectant parents that their personal details would need to be submitted in advance, and a sweep of their home would have to be carried out, too. According to the first lady, those phone calls would go something like, "Thank you for having Malia and Sasha over. Oh, by the way, there’s gonna be a man with a gun sitting outside of your door all night." Michelle continued, joking, "Let him come in and use the bathroom. It would just be nice."

Malia and Sasha Obama often embarrassed their parents

Malia and Sasha Obama aren’t exactly known to be presidential kids who live insanely lavish lives.

Michelle Obama ensured her daughters’ lives were as normal as they could be, constantly reminding them that their father’s job had nothing to do with them (via CBS News). However, raising them to be normal kids — even in the midst of their father’s historic presidential campaign — led to some funny family moments. As Michelle recalled in Becoming (via Express), during an early interview with Access Hollywood, her daughters proved they knew how to lovingly embarrass their dad on national television.

According to the former first lady, Malia — who was 10-years-old at the time — spent the interview earnestly considering every question before answering, admitting her father did annoying stuff like trying to shake her friends’ hands when they came over to play. Contrastingly, seven-year-old Sasha remained mostly nonplussed throughout the interview, interjecting only to enquire as to when they’d all be getting ice cream. However — as Michelle recalled in Becoming — in an especially hilarious moment toward the end of the interview, her youngest daughter gleefully exclaimed, "Daddy had an Afro once!"

Malia and Sasha Obama had to find normalcy in the White House

Growing up, Malia and Sasha Obama played pretend like other kids their age; however, their fantasies were quite obviously influenced by their lives as first daughters. For example, as Michelle Obama revealed to Gayle King during an interview at the 2019 Essence Festival (via USA Today), her daughters’ playtime would often include a wishful game of "pretend-those-armed-Secret-Service-agents-aren’t-there."

In a 2018 interview with The Guardian, the former first lady admitted to initially having concerns about raising her daughters in the White House, saying, "I was extremely worried about raising our daughters in that environment, with butlers ready to bring them anything they wanted and photographers hoping to snap a picture of them any time they stepped foot outside the house," she recalled.

Thankfully, Malia and Sasha turned out to be far more resilient than their mother anticipated. As it turns out, the first daughters were far more interested in being regular kids than they were in the presidential trappings coloring their existence. According to Michelle Obama, Malia and Sasha had curfews, would make their own beds, and would help with household chores as needed — just like regular kids.

Malia and Sasha Obama’s adventures across the globe helped shape their perspective … for better or for worse

For Malia and Sasha Obama, getting to travel and experience different cultures undoubtedly contributed to their impressive transformations into well-rounded, intelligent adults. In Becoming, Michelle Obama recalled a family trip to Rome, Italy — a memorable visit which an eight-year-old Sasha later wrote about for a school assignment. According to Michelle, Sasha nonchalantly noted in the assignment, "I met the Pope this summer. A piece of his thumb was missing."

While speaking with Conan O’Brien during her Becoming book tour, the former first lady read the story about Sasha’s school assignment to the audience (via On Milwaukee), using it as a way to showcase the sometimes mischievous, often hilarious nature of her daughters. However, as Michelle revealed, Sasha’s school assignment also provided insight regarding her eight-year-old mindset.

As Michelle realized, Sasha was small enough during the trip to Rome that she would have been standing at eye level with the Pope’s thumb, and therefore was simply incapable of ignoring it. As the former first lady explained, this realization helped her see the anecdote as a gift rather than an embarrassing moment.

Malia and Sasha Obama handled dating and boys like total pros, thanks to their mom

While Malia and Sasha Obama certainly had a hard enough time making friends with Secret Service agents lurking behind them, one can only imagine how awkward dating must have been for the sisters.

"Imagine trying to have your first kiss [surrounded by] a bunch of men with [guns]," Michelle quipped to Gayle King during a 2019 interview (via People). The former first lady acknowledged how difficult it was once the girls entered their teen years, saying that — aside from worrying about normal stuff like drinking and dating — she and Barack Obama had to worry about the media, as well. "You had to worry about whether your kid was gonna wind up on Page Six," she recalled.

Fortunately, Malia and Sasha never ended up being known as presidential kids who got into weird relationships. As Barack Obama told the hosts of a North Carolina radio show in 2016, this was largely due to their mother (via Time). "She’s such a great example of how she carries herself, [with] her self-esteem not depending on boys to validate how you look," he gushed about his wife.

Malia and Sasha Obama thrived at the White House with a little help from some famous friends

Malia and Sasha Obama’s time in the White House was mostly happy for the sisters, thanks in no small part to Michelle Obama’s commitment to keeping things as normal as possible.

However, the former first lady also credits a handful of notable allies with keeping her daughters’ heads clear while their father was running one of the most powerful governments in the world. During a 2018 appearance on Good Morning America, Michelle gushed about how well her girls turned out and how proud she was of them, making sure to thank the famous ladies who assisted in her daughters’ development.

"I will also say that they had support from a lot of the other former first kids, [such as] Jenna [Bush-Hager] and Barbara [Bush] and Chelsea [Clinton]," she said. Michelle continued, acknowledging how when anything bad was printed about her daughters in the press, Malia and Sasha’s fellow first kids would jump to their defense. "Jenna would get in there and say something," Michelle revealed. She continued, saying, "Chelsea would send a tweet out, and that made a big difference."

Malia and Sasha Obama grew up to have quite the sense of humor

Malia and Sasha Obama generally steer clear of the public eye. However, some stories have inevitably come out about the sisters, leading fans to form pictures of who the girls are — to borrow a word from Michelle Obama — becoming.

In 2018, when Barack Obama appeared on the first episode of David Letterman’s Netflix talk show, the late-night legend shared a funny anecdote about the first time he met Obama’s eldest daughter, Malia, at a party.

According to Harpers Bazaar, Lettermen recounted the story of attending an event at the White House, during which he spotted Malia and headed over to introduce himself. "I go over, and I say, ‘You don’t know who I am. I know your mother and father. My name is Dave Letterman and I am very happy to be here at the party, and thank you for inviting me to the party," Letterman recalled. As he told the former president, Malia immediately delivered a hilariously sarcastic response, telling the late night legend, "Yeah, you look like a guy who really knows how to party." Fortunately, Letterman can take a joke!

Malia and Sasha Obama finally stepped outside of the presidential bubble

Malia and Sasha Obama never seemed as if they were presidential children who were troublemakers. So, as their eldest daughter started branching out on her own, Barack and Michelle Obama’s understandably loosened their reins around her and gave her their trust.

Of course, considering her parents had long been adamant that nothing be published about her in the media without their consent, Malia was somewhat of a mysterious public figure by the time she embarked on her college career. And, unsurprisingly, the mystery surrounding her only made the media that much more interested in Malia — prompting them to release photos and videos she almost certainly would have rather kept private.

Unlike other presidential children looking to present a pristine image, Malia took a gap year before entering college — something plenty of other "normal" kids her age had done (and continue to do). And while Malia herself hasn’t stated her reasoning for doing so, perhaps the eldest Obama sister wanted to put some space between her life as a first kid and her life as an adult woman looking to make a life and career of her own.

Malia Obama made the transition to Harvard with Sasha’s help

While Malia and Sasha Obama may not have been quite as under the microscope when Malia entered the halls of Harvard in August 2017, the eldest Obama was still a noticeable newcomer.

As a piece in the Boston Globe reported, Malia didn’t want to draw attention to herself. In fact, she even politely refused an interview from the publication when approached. And while Malia was recognizable amidst a sea of incoming freshmen, the Boston Globe noted how casually cool and normal she looked standing while standing around and chatting with fellow students.

As Barack Obama revealed in an interview with David Letterman, the whole family helped Malia move in to her new college home (via Harpers Bazaar). The former POTUS also told the late night legend that his youngest daughter, Sasha, tried to play it cool — although it was obvious she was going to miss her big sister very much. "[Sasha is] neater than her sister, so she was helping to make the bed and fold clothes, and just being really quiet about it but in a way that was really moving and touching," Obama recalled.

Malia Obama’s move to Harvard was a transition for Sasha, as well

Considering Malia and Sasha Obama have always seemed to have a super close relationship, it’s not surprising to hear that the youngest Obama sister was sad about her older sibling making the move to Harvard. However, as downtrodden as she might have been, Sasha apparently made a quick rebound.

As Michelle Obama told Ellen DeGeneres during an appearance on her talk show, Malia being away at college meant Sasha scored the best bedroom in the family’s first post-White House home. "She’s got, like, a. living room area and bedroom, and she designed it," Michelle revealed, noting the former president was mad he didn’t get the best room.

According to Michelle, however, it was only fair for Sasha to get the best room. And while Barack might have a smaller room than he would have liked in his life after being president, Michelle joked to DeGeneres that Malia was the Obama with the short end of the stick. "She’s got a room up in the attic somewhere," the former first lady said. She continued, joking, "She’s away at college! You don’t waste rooms on college kids."

Malia and Sasha Obama have forged their own paths

By keeping Malia and Sasha Obama out of the spotlight during their White House tenure, Michelle Obama ensured nobody else would write her daughters’ stories for them, or without their consent.

However, with both ladies college aged and very much forging their own way in life, she took the opportunity to gush a little bit in a 2019 interview with British Vogue about their respective personalities. In the interview, the former first lady noted the resiliency of her daughters, but said Malia and Sasha are otherwise total opposites. "One speaks freely and often, one opens up on her own terms," the doting mother shared. She continued, saying, "One shares her innermost feelings, the other is content to let you figure it out."

Michelle was quick to note, however, that neither of her daughters had the "better" or "worse" approach, as "they’ve both grown into smart, compassionate and independent young women, fully capable of paving their own paths."

Malia and Sasha Obama’s support for each other hasn’t wavered as they’ve grown up

Malia and Sasha Obama are a sisterly dream team!

When the time came for Sasha to head off to college, her big sis was naturally there to help with the move-in process. Speaking to Jenna Bush-Hager on the Today show in 2019, Michelle Obama revealed that it was a tearful send-off as Malia handed her little sister off at the University of Michigan. However, according to the former first lady, the family cried less when dropping Sasha off than they did with Malia. "[We] didn’t want to embarrass [Sasha] because, you know, she had roommates," Michelle revealed.

As the mother of two told People, the family strives to keep major life events — such as dropping her kids off at college — as low key as possible. However, the Obamas did get emotional later that afternoon after saying their final goodbyes to Sasha."You feel a little melancholy that [your daughters] will never be the little ones that sit on your lap and listen to your every word and look at you adoringly," the former first lady revealed on Today.

Malia and Sasha Obama are enjoying being independent women while their parents root for them from the sidelines

For Malia and Sasha Obama, leaving for college was a major milestone. However, the uncharted territory of the college experience is full of highs, lows, and plenty of opportunities to learn from one’s mistakes. And according to Michelle Obama, she wanted to make sure her girls tasted the real world without her watching over their shoulders.

During an appearance on Oprah Winfrey’s 2020 Vision: Your Life in Focus tour, Michelle revealed she follows neither Malia nor Sasha on social media and has no plans to do so (via People). The former first lady declared, "They have to walk their own walk. They cannot define themselves by looking at each other or looking at me or their dad."

According to the mother of two, she simply wants Malia and Sasha to have the breathing room to figure out who they are, to make mistakes, and to just be normal young women. "They have to take the time to get to know themselves. I don’t want them measuring themselves by external influences, and for young girls that is hard to do," Michelle revealed.