Getty images | Instagram/Clifton Powell
Source: Getty images | Instagram/Clifton Powell

Barack Obama Was Not Worried about His Daughters Dating — Meet Malia & Sasha Obama's Boyfriends

Esther NJeri
Apr 29, 2022
07:30 P.M.
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Unlike many parents who often worry about their daughter's dating lives, former president Barack Obama and his wife Michelle were "pretty relaxed" when their daughters started bringing men home. Tag along to meet the men who stole the ex-president's daughters' hearts.


Barack Obama and Michelle's story is something you'd read in a storybook. They first met when Obama was 28 and Michelle was 25. They had both attended Havard, and Michelle was already a year into her position at Sidney Austin, a prestigious law firm in Chicago.

Obama had just landed a job at the firm in a bid to pay off his student loans, and the firm thought it wise to task Michelle with showing the new guy the ropes. 

Barack Obama with Michelle Obama on theNorth Portico of the White House on March 14, 2012 | Source: Getty Images


It was lucky they did, too, because Obama would say: "In the luckiest break of my life, [Michelle] was assigned to be my adviser," adding coyly:

"I remember being struck by how tall and beautiful she was."

On the other hand, Michelle was not impressed. She didn't think Obama deserved all the hype he was receiving at the office, and when he asked her out, she declined — severally. She wouldn't go out with him because she was his boss.


Cornered by their situation, Obama decided if being his boss was the reason she wouldn't go out with him, then he would quit his job, and that's when Michelle finally agreed to go out with him. They had their first date that summer and dated for two years before getting engaged.

In 1991, Obama and Michelle were having dinner to celebrate him passing the bar exam when the waiter came with the dessert and a tray, but a pleasant surprise awaited the future first lady. Michelle recalled the occasion, saying:

"And there was the ring. And I was completely shocked."


Obama then got down on one knee and asked her to marry him, to which Michelle said, "Yes." On October 3, 1992, they walked down the aisle at the Trinity United Church of Christ in Chicago and welcomed their daughters Malia in 1998 and Sasha in 2001.


The Obamas welcomed their first daughter Malia, born Malia Ann Obama, on July 4, 1998, at the University of Chicago Medical Center. She was raised in the Hyde Park neighborhood and then attended the University of Chicago Laboratory Schools before joining the private Sidwell Friends School in Washington D.C. in 2009. 

After graduating, she joined Havard University in 2017, and while not much is known about her time there, she was named a Thomas Temple Hoopes Prize winner for her outstanding coursework.


Then-President Barack Obama with his daughters Malia and Sasha on the Souh Lawn of the White House on January 4 2010 in Washington D,C. | Source: Getty Images

She began her internship at the Smithsonian's National Zoo before becoming a production assistant on the "Extant" set in 2014. She also aided in writing "Girls" in 2015 and served a while at The Weinstein Company in 2017.


In February 2021, reports said Malia was part of the writer's team in the series "Hive," and shortly afterward, would be portrayed by actress Lexi Underwood in the anthology series "The First Lady."

The former first couple's second child, Sasha, born Natasha Marian Obama on June 10, 2001, also grew up in Chicago's Hyde Park neighborhood. Like her older sister, she went to the University of Chicago Laboratory Schools.

Michelle Obama with daughters Malia and Sasha at Galen Center on March 31 2012 in Los Angeles California | Source: Getty Images


While there, she undertook tap dance and gymnastics lessons and played the piano and tennis. After graduating, she attended Sidwell Friends School, becoming a competitive swimmer and playing basketball. She is also involved in the performing arts and was part of the Moscow Ballet for "The Nutcracker" production in 2012.


Sasha and Malia were barely teens when their father became president, and now, they are all grown and have left home. However, Michelle disclosed that she still loved spending time with them and was grateful that the girls chose to stay home during the pandemic. She told Ellen Degeneres, according to People:


"It was an extra special treat to have them. That little bit of time. Because being with them as adults, it's fun! I love them at every age." 

Barack Obama, wife Michelle and their daughters Malia and Sasha at the White House on January 3 2016 | Source: Getty Images


While it is pretty standard for parents to get jittery when their children come of dating ages, Michelle and Obama were not worried when their daughters started bringing men home. 

They had raised their daughters to be responsible people, and one of the reasons Obama was "pretty relaxed" about his daughters entering the dating scene is because, as he would tell ABC News:

 "One is Michelle. She's such a great example of how she carries herself, her self-esteem not depending on boys to validate how you look or you know."

Barack Obama, wife Michelle and their daughters Malia and Sasha, and their pets Bo and Sunny at the White House on April 5 2015 | Source: Getty Images


He also shared that in treating his wife with respect, he hoped his daughter did learn how their partners should treat them once they started dating and that no one should judge them for anything other than their intelligence and character. Speaking to Ellen, Michelle confirmed that her daughter was indeed dating, musing:

"Before, it was just, like, pop bands. Now they have boyfriends and real lives."

It is hard enough navigating the dating scene as a young person, but it is even more intense dating the daughters of the former president. Let's meet the courageous men who chose to go down that path.



Malia Obama with boyfriend Rory Farquharson on January 20 2018 in New York City | Source: Getty Images

Like Malia, Farquharson comes from a prominent family. His father is the chief executive of Insight Investment Management Limited, Charles, while his mother is a qualified accountant.


Born on July 18, 1998, Farquharson grew up in Woodbridge, Suffolk, United Kingdom, and studied law at Harvard. He then joined the Centre for Democracy and Peace Building in Northern Ireland for his internship.

The two lovebirds were first spotted together at the Harvard versus Yale American football game. The video captured Malia smoking a cigarette and then smiling before putting her hands around Farquharson and kissing him.

Malia Ann Obama is seen in Tribeca on April 5, 2017 in New York City. | Source: Getty Images


They were spotted again months later on a casual shopping trip in New York, where, all smiley, they hugged and chatted. The young man also bonded with his girlfriend's family after spending time with them during the pandemic.

As Obama would explain, Farquharson was quarantined with the Obamas during the very early stages of the pandemic due to visa issues. He also had a job set up, and the Obamas took him in. Obama would say of the living situation, as The Sun reports:

"And I didn't want to like him, but he's a good kid."



Two days after Michelle let it slip that her youngest daughter was dating, Sasha was spotted in a purple skirt and looking happy as she strolled alongside her boyfriend. The man in question is actor Clifton Powell's son, Clifton Powell Jr.

The duo is believed to have gotten together when Sasha moved to Los Angeles in 2021 after taking up a course at the University of Southern California. 

Born on May 23, 1997, Clifton Jr. grew up at his family's Ladera Heights home before attending Village Christian High School. After graduating high school, he joined the University of California, Santa Barbara, on a four-year basketball scholarship.


Sasha Obama attends the national Christmas tree lighting ceremony on the Ellipse south of the White House December 3, 2015 in Washington, DC. | Source: Getty Images

However, despite a promising basketball career, he quit the game to work as a scriptwriter. He currently works as a commercial director, creating content for Peloton and Nike. Besides scriptwriting and content creation, he has also ventured into directing.


The Obamas have already accepted Powell Jr. into the family as barely a week after Sasha was spotted with Powell Jr., her sister Malia was spotted hanging out with him. Malia sported baggy blue jeans and a Chicago White Sox T-shirt with braided hair.

On the other hand, Powell Jr. wore a long-sleeved navy shirt with matching sweatpants and a backward baseball cap. The two spent time together strolling a public park before Malia settled on a park bench to smoke a cigarette, as Powell Jr. remained standing. After resting for a while, they continued their stroll.