Sometimes, parents really do know best.
When discussing her daughters Malia Obama (age 27) and Sasha Obama (age 24), Michelle Obama recommended they follow in the footsteps of herself and President Barack Obama.
In the August 6th episode of their podcast, “IMO with Michelle Obama and Craig Robinson,” the former first lady clarified, “I merely aim to keep them receptive towards others.” She added, “To give you an idea, before Barack entered the picture, I had already gained valuable experiences from dating a lot, which allowed me to compare him more accurately.
Michelle, who married Barack in 1992, underscored that her past experiences helped her understand what she preferred and dispreferred in romantic relationships.
The 61-year-old mentioned that they often discuss their past dating encounters with Barack. Their aim is to enlighten the younger generation by revealing these experiences. In essence, my advice is to date extensively. If you come across a disappointing date or have a negative experience, cut your losses and move on promptly. If it’s not going well, simply move on to the next one.
It’s evident from Michelle’s encounters with Barack, who was 64 years old at the time, that there was undeniably a positive dynamic at play. When they first crossed paths – Michelle as a novice lawyer and Barack as a law student – it took some time for her to become comfortable with him.
She remarked that everyone was excitedly discussing him, referring to his initial day at her company. It turned out that all the partners from the Harvard recruitment team were buzzing about a highly talented first-year law student from Harvard, known for his exceptional intelligence.
Michelle, brought on board to help manage law school summer interns, acquired Barack’s records instead.
Initially, when I encountered the name Barack Obama, I must confess a momentary puzzlement. In my mind, I visualized him as somewhat scholarly or perhaps even a bit of a nerd-type individual.
The phone call stirred her curiosity, with her remarking, “His voice was more alluring than my preconceived image of him. It left me somewhat surprised and intrigued, thinking something along the lines of, ‘Wow, this wasn’t what I anticipated.'”.
She clarified that his maturity made him confident, and as a result, they had an enjoyable discussion. However, the only image she had of him wasn’t particularly flattering, so she didn’t feel strongly about him.
Everything really changed when the pair went out to lunch.
She mentioned that he was far more adorable in person compared to his photo. The image didn’t fully capture his charm, which left her impressed by his attractiveness. There was an unexpected appeal about him that she found quite appealing.
She went on to say, “I took him out for lunch and our connection really blossomed during lunch. We had an extended chat, a wonderful exchange of words, and we just seemed to understand each other. If he were here, I’d say there was definitely a spark that ignited between us during that meal.
For more of Michelle and Barack’s most candid confessions, keep reading.
It’s not that Barack Obama, a Harvard Law student at the time, didn’t have feelings for Michelle Robinson – who was his supervising attorney when he interned at her law firm in Chicago during the summer of 1988.
He just hadn’t thought about what came next all that much.
In Michelle’s perspective, marriage was a natural progression – an expected step in a serious relationship as we had. On the other hand, for someone like me, who grew up witnessing my mother’s marriages not enduring, the urge to formally commit to a relationship never seemed as immediate. (This is paraphrased from Barack Obama’s memoir “A Promised Land.”)
They tied the knot Oct. 3, 1992.
As a steadfast supporter of Michelle, I backed Barack tirelessly on his path to the presidency in 2008; however, deep within me, I harbored a secret wish for her husband not to embark on this journey altogether.
He remembered his wife saying, “No, I don’t want you to run for president.” She added, “Gosh, Barack, when will it be enough?” This is taken from the book “A Promised Land.
In June 2025, on the “Wild Card” podcast by NPR, Michelle referred to Barack and her achievements as a shared “team goal,” stating that she reluctantly agreed, perhaps with some resistance phrased as “arguably kicking and screaming.
In her 2018 memoir “Becoming,” Michelle expresses that she had faith in her husband, yet held a troubling secret within – a thought that caused her distress and which she wasn’t prepared to disclose at the time: Although she stood by him during his campaigning efforts, she felt deeply convinced that he might not ultimately reach his goal.
In a conversation with Stephen Colbert in November 2020, the former president admitted that he has not yet fully escaped the consequences of his decision, which subjected his family to an extremely challenging and trying period as they chose to pursue his presidential campaign immediately following a demanding Senate race.
He mentioned that Michelle remained aggrieved over the incident for the entire eight years, with her anger occasionally resurfacing from time to time.
In the heat of my unwavering devotion, I’d have to admit that when my spouse embarked on his political journey, being elected to the Illinois state legislature in 1997, it seemed as though the relentless tide of his schedule eroded our marriage like the ocean against a cliff.
In a 2018 interview with Oprah Winfrey for Elle magazine, Michelle shared that she was struggling to balance things, much like a flag waving in the wind. With two children in tow, she’s working hard to keep everything under control while her husband frequently travels between Washington and Springfield.
Following that, it turned out that “we needed to handle some matters together as a couple,” she explained. “We had to attend counseling sessions to address and resolve these issues.
In 2015, at the White House, Lin-Manuel Miranda, notably, sang a song from his unfinished masterpiece, later known as the massive success “Hamilton.” The president claimed that this performance was so remarkable, you had to hear it to truly believe it.
After discovering that Lin was composing a hip-hop play about Alexander Hamilton, Barack noted in “A Promised Land” that we offered polite encouragement, yet harbored doubts beneath our surface, until he took the stage, began rapping, and the crowd erupted with enthusiasm.
After the initial inauguration of Donald Trump in 2017, where she was merely trying to maintain her composure (as described in her book “Becoming”), Michelle decided she didn’t want to endure such an experience a second time.
During this year, one significant choice I made was deciding to remain at home rather than attend various events such as funerals, inaugurations, and other social obligations that were expected of me. Notably, I also chose not to attend the state funeral for Jimmy Carter in January 2025. In a conversation on ‘Wild Card’, I openly admitted the buzz generated by this decision. Although there was criticism, I took it upon myself and did not regret my choice.
Michelle shared with Wild Card host Rachel Martin that while some might find it morbid, at the age of 61, she hopes to have approximately 25 more summer seasons left if fortune smiles upon her. She emphasized that without consciously considering time, they’ve already been away from work for a decade.
She expressed her preference for “time to move at a leisurely pace for the next decade,” stating that she cherishes life and her own existence, yet fears that if she’s not cautious, the years will pass unnoticed.
Michelle intends to shield her daughters, Malia Obama and Sasha Obama, from undergoing the ordeal of being part of an aspiring first family once more.
During an episode of Kylie Kelce’s Not Gonna Lie podcast in March 2025, she stated that when people inquire if she would ever run, her response is a firm ‘no.’ She explained that those who ask such questions are likely unaware of the sacrifices children endure when their parents hold such roles.
In her words, even though there might be an interest, Michelle expressed concerns about placing her daughters back under the limelight at this point in their lives. They’re currently working on building their own identities and she feels they’ve already had enough exposure to public life.
In June 2025, Michelle said on IMO, “I’m really grateful that we didn’t have a son. Angie Martinez asked her why they hadn’t tried for another child, and Michelle joked, ‘If we had, he would have been just like Barack Obama. I would have felt too much pressure for him.’
Michelle humorously commented on Wild Card, saying, “Even though it may seem odd that people don’t often see us going out on dates as a couple, it doesn’t necessarily mean our marriage is over. Essentially, we aren’t posting every detail of our lives online because, after all, we are both 60.
She also promised that she wouldn’t be demure about it if there was trouble in paradise.
On the April 2025 episode of the Diary of a CEO podcast, she openly discussed that if there were issues with her husband, they would be apparent to everyone. He’d also be aware, and so would everyone else. She clarified that she isn’t one to suffer in silence… Instead, she’d address problems publicly, perhaps saying, ‘Here’s what happened between us.’
In July 2025, Barack joined his sister-in-law and wife for their podcast. He playfully mentioned that any past gossip had been put to rest since she had reconciled with him.
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2025-08-15 21:47