Why Barack Obama Once Labeled Daughter Sasha Obama as “Difficult”

Michelle Obama shared insight into husband Barack Obama’s bond with daughters Malia, 27, and Sasha, 23—including why the former president called their youngest “difficult.”

By Desiree Anello Aug 20, 2025 3:57 PM
| Updated Aug 20, 2025 6:40 PM
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Watch: Why Barack Obama Once Labeled Daughter Sasha Obama as “Difficult”

Barack Obama and Michelle Obama could never pick a favorite child.

But when it came to parenting their daughters Malia Obama, 27, and Sasha Obama, 23, their personalities couldn’t have been more different.

“Sasha is like a cat,” Michelle said during an Aug. 20 episode of her and brother Craig Robinson’s IMO podcast. “She’s like, ‘Don’t touch me, don’t pet me. I’m not pleasing you. You come to me.'”

Adding that Barack would call her “difficult” at times, the former first lady went on to explain that her youngest simply possessed a different temperament and was not a “pleaser” like their eldest.

Because for her part, Malia would often seek out her father to have discussions about politics.

“When Malia was a teenager,” Michelle recalled, “it wasn’t that she was going out any less or doing anything differently. She would tell me, ‘I’m going out this weekend, but I’m going to go in and give dad like 15 minutes.'”

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Michelle Obama's Inspirational Quotes

“She’d go into the Treaty Room and be like, ‘Tell me about Syria,'” she continued, adding that Barack would come out of their meeting saying, “I just had an amazing conversation with Malia.”

And while Michelle does her best to understand both of her daughter’s unique personalities, she previously revealed the dating advice she felt could benefit them both.

"I just try to get them to stay open to people," she explained on her podcast earlier this month. "The thing that I did do was date a lot. When Barack showed up, I had experiences to compare him against."

Indeed, the 61-year-old—who tied the knot with Barack in 1992—emphasized that her dating history ultimately allowed her to learn what she liked and didn’t like in romantic relationships.

"Barack and I talk about our dating experiences," she continued. "We try to educate the girls by sharing our experiences. So my whole thing is date. Date a lot, and if you run into a bad date or have a bad experience, move on quickly. If it's not working, next."

Michelle Obama/Instagram

After all, Michelle—who met the former president when she was a first-year associate at her law firm and he was a law student—was living proof that giving someone a chance could change everything.

"Everybody was abuzz about him," she shared of Barack’s first day at her firm. "All the partners on the Harvard recruiting team were talking about this hotshot first-year Harvard Law student who was brilliant."

"I thought, 'Ugh, what kind of name is Barack Obama?' she quipped. "I had this image of, kind of this nerdy guy."

And though Michelle wasn’t sure there was any chemistry between them at first, it didn’t take long for their romance to take off.

"I had to take him to lunch, and we really hit it off at lunch," she remembered. "We had a long lunch, a great conversation and we just vibed. I would probably say, if he were here, there was a hint of a spark that started at that lunch."

For more of Michelle and Barack's most candid confessions, keep reading.

Barack Obama Was in No Rush to Get Married

Not that Harvard Law student Barack Obama wasn’t in love with Michelle Obama (then Michelle Robinson), the associate assigned to look after him when he was an intern at her Chicago firm in the summer of 1988.

He just hadn’t thought about what came next all that much.

“For Michelle, marriage was a given—the organic next step in a relationship as serious as ours,” the former president wrote in his 2020 memoir A Promised Land. “For me, someone who'd grown up with a mother whose marriages didn't last, the need to formalize a relationship had always felt less pressing." 

They tied the knot Oct. 3, 1992.

Michelle Obama Did Not Want Barack Obama to Run for President

While Michelle publicly supported Barack every step of the way to him winning the presidency in 2008, she really didn’t want her husband to run at all.

“‘The answer is no. I do not want you running for president,’” he recalled his wife saying in A Promised Land. “’God, Barack, when is it going to be enough?’”

On NPR’s Wild Card podcast in June 2025, Michelle called her and Barack’s accomplishments “the team ambition,” which she went along with, “arguably kicking and screaming.”

Michelle Obama Didn’t Think Barack Obama Would Win the 2008 Presidential Election

In her 2018 memoir Becoming, Michelle wrote that she “had faith” in her husband but was “harboring a painful thought, one I wasn’t ready to share: I supported him in campaigning, but I also felt certain he wouldn’t make it all the way.”

Michelle Obama Was Mad at Barack Obama for All 8 Years of His Presidency

“I’ve never fully got out of the dog house for this,” the former president told Stephen Colbert in November 2020. That is, for putting his family “through an extraordinarily stressful, difficult sequence in deciding to run for president, right after I had just gone through a tough [Senate] race.”

And "Michelle stayed angry at me about it," he added. "It would flare up every so often, but she stayed mad about it through all eight years."

The Obamas Went to Marriage Counseling

Michelle confessed that her husband’s schedule once he entered politics—he was elected to the Illinois state legislature in 1997—took its toll on their marriage.

“I’m flailing in the wind,” Michelle told Oprah Winfrey for Elle in 2018. “And now I’ve got two kids, and I’m trying to hold everything down while he’s traveling back and forth from Washington or Springfield.”

Subsequently, there was “work we had to do as a couple,” she said. “Counseling we had to do to work through this stuff."

The Obamas Were Skeptical About Hamilton

Lin-Manuel Miranda famously performed a song from his then-unfinished, future smash hit Hamilton at the White House in 2015. And you had to hear it to believe it, according to the president.

After learning that Lin was writing a hip-hop musical about Alexander Hamilton, Barack wrote in A Promised Land, “We were politely encouraging but secretly skeptical, until he got up onstage and started dropping beats and the audience went absolutely nuts.”

Why Michelle Obama Didn’t Go to Donald Trump’s Inauguration

After spending Donald Trump’s first inauguration in 2017 “trying just to hold myself together,” as Michelle wrote in Becoming, she wasn’t going to put herself through that again.

“One of the major decisions I made this year was to stay put and not attend funerals and inaugurations and all the things that I'm supposed to attend,” Michelle, who also skipped the January 2025 state funeral for Jimmy Carter, said on Wild Card, acknowledging the speculation that was kicked up in her wake. “Those are my choices. Whatever the backlash was, I had to sit in it and own it. But I didn't regret it, you know?”

Michelle Obama Thinks About Death a Lot Because She Loves Life

“My husband thinks this is morbid, but at 61, you know, if I am lucky, if I am truly blessed, I have like 25 more summers,” Michelle told Wild Card host Rachel Martin. “If you're not mindful about time, like—we've been out of office for 10 years.”

She wanted “the next 10 years to go by slowly,” she explained. “Because guess what? I love life. I love my life…But what I feel is that if I'm not mindful about it, the years slip away.”

Why Michelle Obama Will Never Run for President

Michelle will not be putting her daughters Malia Obama and Sasha Obama through the aspiring-first-family experience again.

“When people ask me would I ever run, the answer is no,” she said on a March 2025 episode of Kylie Kelce’s Not Gonna Lie podcast. “If you ask me that, then you have absolutely no idea the sacrifice that your kids make when your parents are in that role.”

Even if she was interested, Michelle added, “The thought of putting my girls back into that spotlight when they are just now establishing themselves…They’ve already served their time.”

Michelle Obama Is Glad She and Barack Obama Don’t Have a Son

“I'm so glad I didn't have a boy," Michelle said on IMO in June 2025. Asked by guest Angie Martinez why they didn’t try for baby No. 3, she cracked, "Because he would've been a Barack Obama. I would've felt for him."

What the Obamas Really Think About Divorce Rumors

“The fact that people don't see me going out on a date with my husband sparks rumors of the end of our marriage,” a bemused Michelle said on Wild Card. “It's like, ‘OK, so we don't Instagram every minute of our lives. We are 60.”

She also promised that she wouldn’t be demure about it if there was trouble in paradise.

"If I were having problems with my husband, everybody would know about it," she shared on an April 2025 episode of the Diary of a CEO podcast. "And he would know it and everybody would know it. I'm not a martyr…And I would be problem-solving in public, and be like, 'Let me tell you what he did.'”

Sitting in on his wife and brother-in-law's podcast in July 2025, Barack joked that the rumors were behind them because “she took me back.”

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