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Former President Barack Obama first introduced his adorable family to America at the 2008 Democratic National Convention. During the historic event, Michelle Obama delivered a keynote address as the leading speaker of the first day, and when Barack finally accepted his nomination at the very end, he was joined on stage by Michelle and their daughters, Sasha and Malia Obama. At the time, the youngest of the family, Sasha, was only 7 years old.

Slowly but surely, the world watched as Sasha grew up in the full glare of the media. She conducted several official duties, like visiting the Children’s National Medical Center alongside her family and participating in the annual National Christmas Tree Lighting Ceremony, all while encouraging Barack’s witty sense of humor at turkey pardoning events. Privately, Sasha progressed in school, joined the workforce, and even formed a new circle of friends long after leaving the White House.

According to her father, Barack, she grew up to be just like her mom, Michelle. When asked if he was afraid of his daughter in a 2020 interview with “Jimmy Kimmel Live!” Barack said, “Yes, and the reason is because Sasha is a mini Michelle, and I’m afraid of Michelle. And Sasha, having seen that, basically has the same look and the same attitude.” Sasha has undoubtedly come a long way since we first met her, and the story of her transformation through the years is one fascinating ride.

Sasha Obama was born in June 2001 to former President Barack Obama and his wife, Michelle Obama. Prior to the Obama presidency, the former first family’s life was nothing out of the ordinary. They lived in a home in the Chicago neighborhood of Kenwood — the family kept the house even after moving into the White House — whose greenery and hidden architecture gems made for a quiet and posh family setting. Sasha and her older sister, Malia Obama, attended the University of Chicago Laboratory Schools in the neighboring Hyde Park community.

The Obamas’ connection to the University of Chicago runs deep; Michelle worked at the institution as the director of community and external affairs while Barack was a lecturer at the law school for more than a decade. Barack was a pretty hands-on parent. The former president would drop Sasha and Malia off at school, and even after he was elected president and was yet to assume office, that didn’t change. The Obama sisters’ upbringing also involved a ton of extracurricular activities like piano lessons, bike riding, and camp.

Before their lives changed forever in 2008, the Obamas prioritized good ol’ family time, with patriarch Barack making tuna fish in the kitchen whenever the mood called for it, and on numerous occasions, they bonded over mutually enjoyable activities. “We’re usually doing picnics and fairs and ice cream parlors, and things that are fun for the kids,” Michelle shared during the family’s chat with “Access Hollywood.”

Sasha Obama began attending Sidwell Friends School in Washington, D.C. in January 2009. In fact, her family’s early move to D.C. before Barack Obama’s inauguration was to help her and Malia Obama have a seamless transition. The Obamas’ choice of school was perfectly presidential since Sidwell Friends School boasts a string of elite alumni, including former first lady Nancy Reagan and former first daughter Chelsea Clinton. The Obama sisters weren’t entirely alone at Sidwell, as former Vice President Joe Biden’s grandchildren were already enrolled at the school.

Over the years, Barack and Michelle Obama maintained their routine of attending parent-teacher meetings, and of course, it wasn’t without the sophistication of their security detail. “I was like, ‘You have to keep showing up, even with all the hubbub, because they’re little girls and you went to their parent-teacher conferences before this,'” Michelle recalled during an appearance on the “Let’s Talk Off Camera” podcast. “So, imagine the presidential motorcade blocking all of Mass Ave. from Pennsylvania Avenue all the way down to Sidwell Friends, with 12 motorcycle escorts, the 10-car motorcade, along with the ambulance and helicopters flying around, pulling up into the school parking lot and having Malia and Sasha horrified.”

Michelle and Barack’s commitment to their parental obligations still showed itself long after Barack had served his two terms. The helicopter parents — no pun intended — defied norms and stayed in D.C. while waiting for Sasha to graduate high school.

After Barack Obama won the 2008 presidential election, he and his family spent their final weeks in Chicago before heading out to his hometown, Hawaii, for Christmas celebrations. The following year, the former first family moved into the Hay-Adams Hotel ahead of Barack’s inauguration, then lived in the Blair House — per presidential tradition — before making the White House their new home. At 7 years old, Sasha Obama became the youngest person to live in the White House since John F. Kennedy Jr., who was born shortly after John F. Kennedy won the 1960 presidential election.

Barack and Michelle Obama tried their best to form a community and offer their children a normal life, since the protocol for simple activities like playdates became more complicated. “The process of having my children at your house meant that an advanced team had to come and question and search your house and ask if you had drugs and guns,” Michelle explained on the “Lets Talk Off Camera” podcast, adding that Secret Service agents would take turns to guard the first daughters as they played, even though they found subtle ways to ease the tension.

Sasha and Malia’s life in the White House also felt more like home because of the presence of their late grandmother, Marian Robinson, who was a trusted guardian whenever Barack and Michelle were busy. “I wanted them to come home to family,” Michelle said in an interview with “CBS Mornings.” “There was just parts of the girls’ lives that I just knew were going to be okay ’cause mom was there. When I travel internationally, grandma was there.”

Sasha Obama played in a rec basketball league as part of a fourth-grade team dubbed the Vipers. The group took on other teams at a local YMCA in Chevy Chase, Washington, D.C., and in true Obama fashion, every weekend was a family sports affair. The Obamas were also joined by former Vice President Joe Biden’s family since Joe’s granddaughter, Maisy Biden, was part of the team. “Imagine that rec league on any given Sunday because we all went, right?” Michelle Obama recalled on “The School of Greatness” podcast. “President, the Vice President … like eight [security] details, because all the kids had details, too.”

Legend has it that former President Barack Obama, who is really passionate about basketball and even secured a position at NBA Africa, started coaching Sasha’s team from the sidelines because their coaches at the time weren’t doing a commendable job. Soon enough, Barack and his then-aide, Reggie Love, became the Vipers’ leading coaches and steered the team toward a well-deserved championship.

Looking back at the moment in his book, “A Promised Land,” the former president wrote, “When the Vipers won the league championships in an 18-16 nail-biter, Reggie and I celebrated like it was the NCAA finals.” As coach, Barack achieved more than a championship because being on Sasha’s team had made for the perfect daddy-daughter bonding time. Unfortunately, he soon had to step down when politics among parents began to outweigh the common goal: winning and teamwork.

The Obama sisters, though privileged, are no strangers to hard work. In 2016, 15-year-old Sasha Obama landed a summer job at Nancy’s, a seafood restaurant in Martha’s Vineyard, Massachusetts. Sasha, who was supposedly in disguise and was using her real name, Natasha, worked in the restaurant’s takeout section as a cashier. Still, the presence of a security detail at the joint obviously put her in the spotlight. A coworker who was on shift at the time told The Boston Herald, “We were wondering why there were six people helping this girl, but then we found out who it was.”

It made sense for Sasha to take up a job on the island because her family frequented it during the summer and eventually secured an oceanfront property in it for a reported $11.75 million in 2020. Martha’s Vineyard is a known celebrity hotspot and has been the go-to for the likes of former first lady Jackie Kennedy Onassis and media mogul Oprah Winfrey. Sasha has since secured other jobs, and they have nothing to do with working the till. Her name was seen in the credits of Season 4 of the Showtime series, “Couples Therapy,” in which she was credited as an interviewer. Sasha seems to have followed in the footsteps of her sister, Malia Obama, who is a budding director with growing influence in Hollywood.

Driving lessons for children living in the White House have evolved over the years. Back in 1996, former first daughter Chelsea Clinton was taught how to drive by her father, the then-president, Bill Clinton, and by the time former President Barack Obama assumed office, he and Michelle Obama were forbidden from getting behind the wheel. As such, first daughters Malia and Sasha Obama had to learn driving with the help Secret Service agents. “They wouldn’t allow us to ride in the car with them,” Michelle recollected during an appearance on “The Late Show with Stephen Colbert.” The lessons, she said, were carried out in the Secret Service driving range and were quite ballsy since the first step involved sudden acceleration and halting.

The Obama sisters were allowed to drive themselves around after getting their licenses, often with Secret Service agents in sight. Sasha has been pictured driving herself on more than one occasion, and unfortunately, she was once involved in an accident, as Michelle revealed in a conversation with the “Not Gonna Lie” podcast. “One time, Sasha got T-boned,” Michelle recalled. “Literally, her car totaled. Some lady T-boned her, and you get this call that Sasha was in an accident, the car was totaled. And then I thought, ‘Oh, I hope the lady that hit her is okay.'”

Although the entire Obama family is Ivy League-educated — Michelle and Barack Obama are alumni of Harvard Law School, while Malia Obama also studied at Harvard — Sasha Obama veered from family tradition and attended the University of Michigan as a sociology major. Sasha had an eventful life in college, and initially, there was a buzz surrounding her fall of 2019 admission. “We’ve like, kind of grown up hearing about her and her family, so I mean, it’s just very cool to be maybe going to the same school as her,” one student said in a chat with WXYZ-TV.

When Sasha finally showed up to college and was accompanied by Secret Service agents to orientation, there were mixed reactions to her presence. Some students were excited, while others were indifferent toward the hype. “I was walking by pushing a vacuum and she walked out right in front of me,” Zach Lassen, another student at the institution, told The Detroit News. “I said, ‘Excuse me.’ It was a crowded hallway with her and some Secret Service dudes.”

The following year, Sasha was among millions of students who were affected by the COVID-19 pandemic and had to learn from home. In an Instagram live session with singer Jennifer Lopez, Michelle said of Sasha and her sister, Malia, who was yet to graduate from Harvard University at the time (via People), “My girls are studying from home. We’re itching to get back to campus, but things are just confusing … not quite safe. I’m just glad that they’re staying put, even if they’re sick of me.”

Sasha Obama’s love life has often remained private, but through the years, a couple of details have found their way to the public. In 2017, Sasha was pictured kissing a guy identified as Matt Metzler at Lollapalooza, and in 2019, she went to prom in the company of an unconfirmed boyfriend named Chris Milton. Afterward, nothing serious seemed to be happening in Sasha’s romantic life until April 2022.

In a chat with “The Ellen DeGeneres Show,” Michelle Obama revealed that both Sasha and Malia Obama were exploring the dating field, saying, “Now they’re bringing grown men home. Before it was just, like, a pop band. Now they have boyfriends and real lives, and all that stuff, but, yeah, they have grown up right before our very eyes.” That same year, Sasha and Clifton Powell Jr., the son of “Deep Rising” actor Clifton Powell, sparked dating rumors after the pair was seen walking together in West Hollywood.

During a June 2022 appearance on the “Dear Fathers” podcast, Powell confirmed that Sasha and Powell Jr., who is a former basketball player-turned-Hollywood director, had been dating for at least a year. He further delved into his own shady relationship past, which he blamed on a lack of role models, and revealed that his son’s relationship with Sasha sparked the need for proper mentorship. “I have an opportunity and a responsibility to make my son responsible, gentle, kind, loving, and supportive — the things that I did not get taught,” Powell said, and continued, “So I text him all the time, and I say, ‘Treat Sasha like you would want somebody to treat your daughter.'”

Sasha Obama transferred to the University of Southern California sometime before her junior year and became roommates with her sister, Malia Obama. The Obama sisters personalized an apartment by scouting for good deals on yard sales and getting additional items from IKEA, much to Michelle Obama’s delight. Moving in together was the girls’ idea, and although Michelle was more than elated, she tried to maintain her composure when they first broke the news. “I just said, ‘Okay, well that’s interesting that you guys are going to try living together. We’ll see how it goes,'” Michelle shared in a conversation with People. “But yeah, it feels good to know that the two girls you raised find solace at a kitchen table with one another. It’s like the one thing you want for them.”

Much of Sasha’s life at USC remained under wraps, but she made several headlines for her fashion choices. Her style has evolved from the preppy chic of her White House days to become more earthy and flowy, with some risqué outfits that exposed her killer body. Since leaving the White House, Sasha has rocked two daring outfits, including a beige crop top, which she paired with a set of baggy jeans that she wore over visible underwear. Similarly, Sasha channeled her inner boho chic when she was pictured around campus in a patterned maxi skirt and a folded blouse that was tucked under a multicolored bralette, all while exposing her pierced navel and flaunting beaded accessories. Sasha eventually graduated from USC in 2023 in a ceremony that was attended by her famous family.

Living on the West Coast meant that the Obama sisters were miles away from Barack and Michelle Obama, who appeared to pursue permanent residence in Washington, D.C when they purchased an 8,200-square-foot home after leaving the White House. Sasha and Malia Obama still stayed in touch with their parents through a family group chat, but ultimately, they had to establish their own social circle and adapt to living in Los Angeles. The pair has been photographed at numerous events, including a Drake afterparty that they attended in August 2023 and singer Billie Eilish’s 2024 Halloween party, which was a star-studded affair.

In April 2025, Sasha and Malia were pictured celebrating Easter Sunday at a picnic with friends. In one photo, Malia was seen walking beside producer Tiler Wilson while Sasha and an unidentified male companion trailed behind them. That same month, the siblings were photographed at singer Destin Conrad’s “Love on Digital” release party, and as usual, Sasha continued her streak of wearing daring outfits. She was pictured in a white crop top that exposed her midriff, which she paired with a set of blue jeans. Needless to say, Sasha doesn’t try to hide her party girl lifestyle anymore. In June 2025, she was photographed having a good time at the club with a group of friends that included KATSEYE girl group member Manon Bannerman.