Barack and Michelle Obama’s Love Story Is Even Better Than You Thought

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

As a seasoned observer of political and social dynamics, I have had the privilege to witness many iconic moments throughout my years. However, the tender, heartwarming, and often amusing moments shared between President Barack Obama and his First Lady, Michelle Obama, during their tenure, stand out as some of the most memorable.


If there’s a remarkable woman standing behind every outstanding man, then let’s save our highest praises for Michelle Obama.

Though the former first lady would probably implore you to take it down a notch.

Michelle has repeatedly emphasized that she and her husband, ex-President Barack Obama, are simply ordinary individuals trying their best day by day. This might surprise those who viewed them as almost superhuman, not just personally but as a model couple, the epitome of what a successful marriage should be.

Or at least as one of the most admired couples to ever call the White House home.

“Michelle admitted in a January podcast with Jay Shetty on ‘On Purpose’, that over the course of 31 years, we’ve made many errors, and even now, we’re still stumbling, but with each passing moment, we are improving. It just gets progressively better.”

She expressed, “I wouldn’t give up my marriage for anything, despite its challenges and the tumultuous events like running for presidency… Indeed, it has been a massive, influential part of our lives. However, the positive experiences have outnumbered the negative ones. If we hadn’t persevered, we would have missed out on all the goodness that came our way.”

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In 2022, the author who penned “The Light We Carry: Navigating Challenging Times” at the age of 60, has had numerous joyful moments with the 44th president, who celebrates his 63rd birthday on August 4.

In her memoir “Becoming” published in 2018, Michelle Obama aimed to dispel the popular narrative surrounding Barack Obama, the United States’ first Black president and herself, the first Black First Lady. They found themselves under an unparalleled level of expectation while under intense global scrutiny.

In an interview with Sarah Jessica Parker in December 2018 during her book tour at Brooklyn’s Barclays Center, Michelle explained that she and Barack worked diligently for eight years to achieve perfection because they didn’t have room for mistakes. She added that this was something they were accustomed to since when you’re the first or the only in a position, the expectations are high and constantly changing as they are met and surpassed.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

She shared with Good Morning America’s Robin Roberts, “I encounter numerous young couples facing challenges, and I believe they may feel as though there’s something amiss about themselves. However, let them understand that the Obamas—who have an exceptional marriage and deeply care for each other—also invest effort in their relationship and seek help when necessary.”

In an interview with People magazine back in November 2018, she expressed, “Given our role as role models, it’s crucial for us to speak truthfully. If you find yourself contemplating leaving a marriage, that’s not uncommon – because I’ve felt the same way.”

But the intimate look at her family life in Becoming proved unexpectedly relatable in many ways.

In one of her deepest confessions, Michelle shared that she underwent a solitary, agonizing, and disheartening experience when she had a miscarriage. Later on, the Obamas resorted to in-vitro fertilization (IVF) to welcome their two beautiful daughters, Malia Obama, now 26 years old, and Sasha Obama, who is 23.

The Obamas sought counseling, as Michelle was hoping that the therapist might help in resolving some issues with her partner.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

But the intimate look at her family life in Becoming proved unexpectedly relatable in many ways.

In one of her most intimate disclosures, Michelle revealed that after experiencing a solitary, agonizing, and disheartening miscarriage, she and Barack underwent IVF treatments to conceive their two daughters, Malia (age 26) and Sasha (age 23).

The Obamas sought counseling, as Michelle hoped that the therapist could help improve their relationship.

She confided to Oprah Winfrey at the packed event in Chicago’s United Center, which kicked off her book tour in November 2018, that she intended to involve another person to convey to him, “Pull yourself together.”

In her summary, she realized that it wasn’t her partner’s responsibility to make her happy; rather, we should strive to make each other content. There was a piece of herself expecting him to fulfill her needs, and she didn’t require his actions, she needed the tasks accomplished. The conflicts were not about whether the tasks would be completed but about who would complete them.

In simpler terms, if it weren’t for a few unexpected events, nothing would have been accomplished and history might not have been changed. Some of these events are depicted in the movie “Southside With You“, which tells the story of Barack and Michelle Obama’s first date in 1989. However, other circumstances didn’t quite fit the romantic fairy-tale narrative we usually see.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

A student at Harvard Law School named Barack Obama (also known as Barry by some friends) had recently begun his summer job at the law firm Sidley & Austin in Chicago. At that time, he was 27 years old. Upon his arrival, he was instructed to report to Michelle Robinson, a fellow Harvard Law graduate from the class of ’88, who was also 25 years old.

By multiple accounts, including his own, he was instantly smitten.

In a video message during their chat, Barack reminisced about his first encounter downtown. It happened to be a rainy day, and he didn’t have a proper umbrella. So, he was running late and a bit wet when he entered Michelle’s office, leaving the question of whether he made a good first impression unclear.

Michelle found herself charged with guiding the new recruit, a role she later described as “the greatest stroke of luck” in an article about their initial encounter for O Magazine. Contrary to her expectations, based on his unique name and the buzz surrounding him, she believed he would be odd or excessively intellectual.

Barack remarked in O, “I was amazed by her towering height and breathtaking beauty.” Later on, he discovered that she found his nose and ears to be smaller than they appeared in the photograph he had sent for the company directory.

Michelle remembered thinking, as David Mendell wrote in his 2009 biography “Obama: From Promise to Power”, that the man sounded almost too perfect, too good to be true. Given her past experiences with other men who had similar reputations, she assumed he was one of those charming fellows known for their smooth talk and ability to impress. They met for lunch, and he wore a tacky sports jacket and casually held a cigarette, which reinforced her initial impression: ‘Ah, here we go again. Here’s another good-looking, suave-talking guy. I’ve been here before.’

Later, I was genuinely surprised to discover he possessed the ability to interact with others and had more layers than initially perceived. It was revealed that he was a distinguished individual, upholding robust moral principles.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Michelle shared with Marian Robinson, her mother, that she intended to prioritize her career and temporarily step away from dating. Additionally, she expressed worry that the appearance of the two Black associates at the law firm being in a relationship might seem somewhat inappropriate or unrefined, she mentioned, as reported by Mendell. It’s worth noting that Newton Minow, a partner at Sidley Austin, told Liza Mundy for her 2008 book “Michelle” that there were other Black lawyers at the firm, including a partner. However, Minow could understand why Michelle might have felt otherwise.

She even tried to set Barack up with a friend, but he wasn’t interested. 

In the book “O“, he expressed that she graciously accompanied him to a few social events, yet never criticized his mismatched and unstylish attire. He admitted to asking her out, only for her to decline each time. Despite his repeated attempts, she consistently turned him down, stating it would be inappropriate.

As a die-hard fanatic, I’d go so far as to step down if given the chance, just to share an ice cream date with her. Miraculously, she consented, and we embarked on a momentous journey to Dorchester and East 53rd Street. Now, there’s a commemorative plaque that marks our unforgettable outing. It quotes Barack from his memoir, “O”: “On our first date, I indulged her with the best ice cream Baskin-Robbins had to offer, our makeshift table serving double duty as the curb. I kissed her, and it was like savoring a piece of heavenly chocolate.”

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

But really, there could be plaques all over the city.

In the movie “Southside With You“, the man who would later become president asked Michelle out for a date, and he picked her up in an old yellow Datsun – a car that the future president truly owned. This encounter took place before he had a scheduled speech.

Initially, they visited the Art Institute of Chicago to explore an exhibition, had lunch, she found herself captivated by his speech (she swooned, naturally), they attended a screening of Spike Lee’s “Do the Right Thing,” where they unexpectedly bumped into a colleague and his spouse, and eventually shared their first kiss over some ice cream.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

“Michelle mentioned years later in a promotional video for the White House, ‘Our date was really enjoyable.’ We spent the entire day together, and he revealed different aspects of his personality. He shared his cultural side with me, and afterwards, we strolled along Michigan Avenue for quite some time.”

It was Newton Minow and his wife who saw young Barack and Michelle at the movie theater that night.

“I think they were a little embarrassed,” he told Mundy.

Mary Carragher, a colleague from Sidley Austin, mentioned that she noticed small details about him. Carragher, along with others, believed Michelle felt the same affection for Barack as he did for her. She was in the process of discovering more about him and growing fond of him. Carragher described Michelle as being quite captivated by him, almost in awe.

That being said, Carragher added, Michelle “was not falling all over him. She was very cool.”

In her book “Becoming“, Michelle reveals that once she let herself feel something for Barack, a powerful wave of emotions overtook her – a tumultuous mix of longing, gratitude, contentment, and awe.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Michelle’s brother, Craig Robinson (who is the executive director of the National Association of Basketball Coaches), remembered having a sense of pity for Barack Obama when Michelle initially brought him home for dinner, as he believed that Barack would likely leave after a few dates, much like previous suitors.

In my professional opinion, he was incredibly laid-back. What struck me most was his affectionate manner of discussing his loved ones, reminding me strongly of how we talk about our own family circle. I found myself thinking, “What a genuinely kind man, a pity he might not make it in the long run.” His father, Fraser Robinson III, shared similar sentiments.

However, Michelle found him appealing, as per Craig’s statement, due to two main reasons. Firstly, Barack demonstrated intelligence without coming off as superior to others. Secondly, he had the ability to handle Michelle’s sister’s character effectively.

As a lifestyle enthusiast, I found myself returning to Harvard at the end of an enchanting summer, yet that didn’t hinder my cherished connection. Instead, we navigated the distance with determination and love.

“Michelle came into my life when I was still quite immature, not yet ready to maintain something like that,” Barack shared with Mendell, who recalled that prior to Harvard, while working in Chicago as a community organizer, the future president had been in a committed relationship and owned a cat. However, their friendship had faded over time.

Which was pretty much true—though as tends to be the case, it wasn’t that simple.

Before he assumed the presidency, Obama mentioned in his memoirs that he had a condensed series of relationships prior to meeting Michelle.

Based on David Maraniss’ 2012 biography titled “Barack Obama: The Story”, a woman named Genevieve Cook was Barack Obama’s most significant romantic partner in his young life, whom he encountered in New York in 1983 following his graduation from Columbia. However, when she expressed her love by saying “I love you”, he responded with a simple “thank you”.

Genevieve thought of her former boyfriend, who was known for his regular morning runs and strict writing habits, as a virtuous daily jogger and disciplined writer. In his 1995 book, Dreams From My Father, Barack spoke about his sister, Auma, saying he had pushed Genevieve away and they began to argue. He mentioned, “We started to fight. We started thinking about the future, and it loomed over our comfortable little world.” By May 1984, they had parted ways, and Barack relocated to Chicago following their split.

In the year 1985, during springtime, a 25-year-old man named Barack crossed paths with Sheila Miyoshi Jager, who at that time was pursuing her PhD studies at the University of Chicago. In the book by Maraniss, she is simply identified as “the Chicago anthropologist.” This encounter took place through mutual acquaintances. As Maraniss put it, this relationship followed a similar pattern to Barack’s previous one with Genevieve, ending when Barack was prepared for his next professional step.

Once again, not so simple.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In his book “Rising Star: The Making of Barack Obama” published in 2017, David Garrow explains that Barack and Sheila got engaged in 1986 following their move into a shared apartment on South Harper Avenue, which cost them $450 per month.

“Dear friend, as swamped as I am and naturally compatible in our temperaments, Barack here confesses,” he penned. “Don’t get me wrong, there are stressors. Sharing space constantly isn’t my forte, and sometimes I yearn for the silence of bachelorhood. However, with winter looming, it’s comforting to have someone waiting at home after a long workday. It’s all about finding a balance, balancing priorities.”

Months after passing, during the cold season of ’86, when we paid a visit to my parents, he proposed marriage to me, as Sheila reminisced.

Due to her parents’ opinions—her mother found Barack appealing but felt her child was still too young; her father disapproved of the young man—she responded by saying “not now.” Despite this, they continued their relationship for nearly another two years.

In early 1987, Sheila shared with Garrow that her boyfriend, who initially seemed quite ordinary to her, transformed into an extraordinary individual after he embarked on his journey. At that point in time, it was evident to her that he harbored aspirations of becoming president. Simultaneously, Sheila (a woman of mixed heritage, half white and half Japanese) noted that he began exhibiting brooding, quiet, and distant behaviors. It was around this period that he started discussing his political ambitions, and the topic of race became a significant point of contention between them.

Despite this, Barack extended an invitation to Sheila to join him in Hawaii to meet his family during Christmas in 1988. However, by then she had come to understand that their relationship wouldn’t align with their individual goals and aspirations. Barack was enrolled at Harvard that autumn, but Sheila had vacated their Chicago apartment prior – rumored to be after discovering a journal hidden beneath the bed, which he kept secret.

They stayed in touch that first year, though.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Following Barack’s graduation from law school, Michelle had not yet made up her mind about their joint future. She requested her brother to extend an invitation for her boyfriend to join a casual game of basketball, as she and her father believed this was one of the best methods to gauge someone’s genuine character.

In her book, Becoming, Michelle noted that Craig’s viewpoint on Barack was significant for both myself and my brother, who had a knack for understanding others, particularly within the realm of games.

In an interview with the New York Post in December 2018, Craig shared that he had come to understand that the person wasn’t selfish. Instead, they were unselfish and demonstrated good character on the court. They would call fouls and even give up fouls when necessary. Trusting your teammates is essential in pickup games, he noted, as they’ll make the right decisions. This individual did just that. Craig went on to tell his sister that he thought highly of this person, emphasizing that they didn’t only pass him the ball because they were dating his sister.

In the course of time, it’s been noted that Barack harbored some doubts about the concept of marriage. This was evident even when he proposed to Sheila.

During their long-distance relationship, Michelle shared her expectations with him, and he responded that marriage wasn’t crucial as long as they remained a couple.

To paraphrase Michelle: Yeah, no.

In 1991, during a lavish dinner at Gordon in Chicago, he expressed to her that while he deeply loved her, he struggled to comprehend the purpose of their relationship. She later shared this in her book “Becoming”. This statement left her feeling flushed with embarrassment…Was this the right moment for such a conversation?

The box with the ring arrived on a dessert plate.

On October 3, 1992, Michelle Robinson tied the knot with Barack Obama at Chicago’s Trinity United Church of Christ. As her father had passed away in 1991, her brother stood in his place and escorted her down the aisle.

Craig shared with the Post, recalling his post-game gesture towards his soon-to-be brother-in-law, that he didn’t quite secure the win, but he steered things in a positive direction. He admitted there was a chance he could have hindered their progress, but ultimately it was up to them to seal the deal.

1998 saw the birth of Malia, while Sasha followed in 2001. One significant life event leading them to seek advice was the transition into parenthood. This change motivated them to visit a counselor.

Michelle shared with Robin Roberts that marriage counseling was an effective method for us to learn how to express our disagreements constructively. She mentioned many young couples who face struggles and feel there might be something amiss with them, and she wishes to make it clear that even the Obama’s, who have a strong, loving marriage, invest time and effort into their relationship. When needed, they seek outside help as well.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In my latest book, “Becoming,” I share an insightful moment: When Barack assumed the presidency, he found himself enveloped by individuals whose primary duty was to cater to his every need, reminiscent of a bygone era where households revolved entirely around the man. This contrasted starkly with my vision for our daughters’ upbringing, as I wanted them to grow up accustomed to a more balanced and egalitarian lifestyle.

During the 1980s, it seemed everyone understood his presidential aspirations, but Michelle claims she was unaware of these ambitions while they were courting.

Craig confided in Liza Mundy that Barack had disclosed to him, during an early party gathering, his ambition to pursue a career in the U.S. Senate and possibly even strive for the presidency at some point.

It seems more appropriate for him to have expressed: “Keep Michelle informed, would be best!” Instead, Michelle learned from Mundy in 2007 that he indicated his sister was aware of the situation. However, Craig stated to Vanity Fair that his sister had been cognizant of what she was dealing with.

Growing up, I had a unique perspective on politics due to my father’s long-standing career with the city of Chicago and his role as a Democratic Party precinct captain. This early exposure offered me an insight into the intricacies of political maneuverings, but it wasn’t always a pleasant sight, especially when it came to the cronyism that I often observed. Fraser Robinson, my father, never appreciated such underhanded practices.

In her book, Michelle expressed that she wasn’t fond of politicians and initially found the concept of her husband entering politics unappealing. However, as time went by, she realized, “If Barack felt he could make a difference through politics, why should I stand in his path?”

He was elected to the Illinois Senate in 1996 and then the U.S. Senate in 2004.

In 2004, while serving as the executive director of community affairs at the University of Chicago Hospital, Michelle expressed to the New Yorker during her Senate campaign that she was employed and primarily responsible for two exceptionally intelligent young girls. She described her life as chaotic and unrealistic.

Living as a politician’s wife was not an easy task, she admitted. This is one reason why Barack is so appreciative.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In a conversation with Oprah for O around the same time, and prior to the 2004 elections, Michelle expressed her sentiment, “I’d be thrilled to have Barack as my senator. I truly know this man; he’s intelligent, honest, and everything you could hope for.”

Asked the role his family played in his life, Barack said, “They’re everything.” 

He said, “I love this woman. We’ve had our rough patches…” Michelle agreed, “There were many.” 

She shared with Winfrey that their top priority is not to let down their children, as Barack is an exceptional father. Despite being away, he makes sure to call every evening. People can be selfish and forget that you have responsibilities like attending your children’s ballet performances and parent-teacher conferences. Yet, Barack finds joy in these commitments.

However, it was challenging for her. As detailed in her book “Becoming,” when her husband was a state senator and she was juggling full-time work and family life, striving to find time together as a family, she ultimately had to establish a consistent bedtime routine and make it clear to her spouse that if he wanted to put the children to bed, he needed to be present, plain and simple.

In her own words, this instance served as a turning point, a moment where she halted her downward spiral. Using an analogy, she compares herself to a mountain climber on the verge of slipping from a frosty summit, emphasizing that just as the climber stabs an ax into the frozen ground to prevent falling, she too found a way to stop and regain control.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Michelle didn’t show much excitement when her husband mentioned he wanted to run for presidency. However, she immersed herself wholeheartedly in the campaign and stood by him, or in various parts of the country, mobilizing support as needed, throughout his campaign.

In a conversation with the New York Times in 2007, she expressed a blend of doubts and wholehearted backing when she asked, “Who could confidently declare, ‘I’m prepared to be president and first lady?'”

Michelle expressed, “Barack is extraordinary, and that’s why I’m here.” She also admitted in her book, “I agreed to be with him not only because I admired him, but also because I believed in his abilities. To be honest, I didn’t fully expect him to win.”

As a die-hard fan, I can’t help but reflect on the incredible journey of these two individuals who spent two terms in the White House, a span of seven years that irrevocably altered their lives and history itself. Yet, beneath the power and influence, they remain the same couple who exchanged vows nearly 32 years ago – best friends and partners bound by shared experiences. They’ve scaled the heights of power, felt the invigorating sting of starting from scratch, reveled in the ecstasy of success, and weathered the storms of failure. They’ve grappled with the torment of indecision and savored the sweetness that comes with knowing they made the right call.

Michelle shared with People that she and [her partner] are reconnecting. “We often eat meals together privately and have long stretches of time that are only the two of us – reminiscent of when we first started: without children, without the spotlight, without any distractions. Just us, pursuing our dreams.”

Which is just how they started. Though they probably don’t miss the yellow Datsun.

As a devoted admirer, I invite you to continue perusing for the heartwarmingly inspirational moments in the journey of Barack and Michelle Obama’s marriage.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

As a lifestyle guide, I can share a compelling narrative: After spending eight years in the White House and seven more years down the line, their lives – and history itself – have been irrevocably transformed. Yet, they remain the same pair who pledged their love nearly 32 years ago. Simply put, they’re best friends and partners who have walked together through the heights of power, the exhilarating struggles of starting anew, the ecstatic highs and crushing lows, the torment of uncertainty, and the contentment that comes from knowing they made the right decision.

Michelle shared with People that they are reconnecting. “We often dine together privately and spend significant moments alone – much like the way we were at the beginning of our journey: without children, without the spotlight, without any distractions. Just us nurturing our dreams,” she explained.

Which is just how they started. Though they probably don’t miss the yellow Datsun.

Continue scrolling for the most heartwarmingly inspiring moments captured in the relationship between Barack and Michelle Obama.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In July 2020, Michelle discusses her marriage on her podcast, revealing one reason she fell for her partner was their shared belief in the principle that people should look out for each other like family. She explains that her upbringing, including her family, neighborhood, and sense of community, instilled this perspective in her, which influenced the decisions she made throughout her life as she saw those experiences shaping hers as well.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The couple uplifts graduates during the Dear Class of 2020 event.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

As they anticipate meeting, the pair shares warm grins while standing by to welcome President Lee Myung-bak and his spouse, Kim Yoon-ok.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Capturing a heartwarming scene: During Mother’s Day celebrations at the White House, President Obama shared a touching moment with Michelle.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Back in 2018, I had the privilege of revealing my official portrait during an elegant ceremony held at the Smithsonian’s National Portrait Gallery. It was truly a memorable moment!

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The duo hands out candy to trick-or-treaters on the south lawn of the White House.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The president places a gentle kiss on his wife’s cheek.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Michelle prepares the president for a friendly greeting, such as a handshake, prior to their encounter with Singapore’s prime minister.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Before interacting with Lee Hsien Loong, the Singaporean Prime Minister, and his wife Ho Ching, the President offers them a sign of approval.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

Prior to the encounter with former Indian Prime Minister Manmohan Singh and his spouse Gursharan Kaur, they exchanged furtive glances.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

President Fonz gives the camera a thumbs-up while Michelle looks equally bemused.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The adorable couple makes each other giggle before meeting with Italian Prime Minister Matteo Renzi and Agnese Landini.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

2012 found me overjoyed and breathless, as I watched my beloved duo share a heartfelt, lengthy hug – the moment they learned they’d continue their journey together as President and First Lady for another four years.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In January 2013, the President and his significant other marked his re-election with a leisurely dance at the Commander-in-Chief’s Ball.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The two share a slow dance at the Neighborhood Inaugural Ball in 2009.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

The pair showcased their radiant grins while dancing at the Obama’s Home State Inaugural Ball back in 2009.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

In 2008 at the Democratic National Convention, the duo basked in the experience of that significant moment. It was after then-Senator Obama had officially been recognized as the first African American to headline a major political party’s nomination.

Barack and Michelle Obama's Love Story Is Even Better Than You Thought

At a Minnesota rally, the pair expressed their joy following Senator Obama’s discovery that he had secured the Democratic presidential nomination in June 2008.

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2024-08-04 13:21