Barack and Michelle Obama's Love Story Isn't What You Thought It Was—It's Even Better

Barack Obama, the 44th president of the United States may not have ended up in the White House if he hadn't realized that Michelle Robinson from Chicago was the woman for him.

By Natalie Finn Aug 04, 2021 2:01 PMTags

If behind every great man there's an even greater woman, what sort of superlative should be reserved for Michelle Obama?

Well, the former first lady might implore you to turn it down a notch, for starters.

While on her cross-country book tour in support of her best-selling memoir, Becomingthey had to add 2019 dates due by popular demand, naturally—Michelle made it clear that she and her husband, former President Barack Obama, are at the end of the day only a couple of human beings doing the best they can. Which may have come as a shock to the millions who've put them on a pedestal, not just individually but as a unit, as the end-all and be-all of what marriage should look like.

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

In fact, in December 2018 the Obamas topped Gallup's respective annual polls ranking the Most Admired men and women alive.


Barack and Michelle Obama's Sweetest Moments

But Michelle, with Becoming, effectively and purposely punctured the myth behind the couple who made history as the United States' first African-American president and first lady—and who had no choice but to figure out how to shoulder an unprecedented amount of expectation in the glare of the world's most demanding spotlight.

Which, in turn, probably made them all the more admired.

"Barack and I spent eight years trying to operate in complete perfection because we didn't feel like we had a margin for error," Michelle told Sarah Jessica Parker in December 2018 when her tour stopped at Brooklyn's Barclays Center for a Q&A. "Which we were used to, because oftentimes when you're the first or the only, the bar shifts a lot. The bar gets set, you meet it, you exceed it, they move the bar."

Leigh Vogel/WireImage

"I know too many young couples who struggle and think somehow, there's something wrong with them," she told Good Morning America's Robin Roberts. "I want them to know that Michelle and Barack Obama—who have a phenomenal marriage and who love each other—we work on our marriage and we get help with our marriage when we need it."

"Because we're role models," she told People in November 2018, "it's important for us to be honest and say, if you're in a marriage and there are times you want to leave, that's normal—because I felt that way."

Inside Barack and Michelle Obama's New World Since Leaving the White House: A Rental House, Personal Twitter Accounts & SoulCycle

The former first couple had only recently gone on a trip to Palm Springs, Calif., that was just the two of them, as in no kids and no famous friends, and Michelle reflected on how nice that was.

"We swam, we sat, and he wrote because he's still writing his book. So he's a little resentful," she teased.

Her written recollections span the duration of her life, from girlhood and law school to what it was like in 2017 to leave the keys to the castle in the hands of Donald and Melania Trump (who, Michelle said, had not called her for advice, though the line remains open).

"By the time we got on that plane and closed the door, I wept," Michelle told SJP. "I told Barack, 'That was so hard. What we did, and how we had to do it, was so hard.'" 

Watch: Michelle Obama and the Power of Fashion: Scenes From NYFW

But it's the intimate look at her family life that proved particularly relatable for so many.

Among the most personal revelations: After Michelle suffered a miscarriage, which she describes in the book as a "lonely, painful, and demoralizing experience" for her, the Obamas proceeded with IVF to help conceive both of their daughters, Malia Obama, now 23, and Sasha Obama, 20. And the Obamas have been to counseling—because Michelle was hoping the therapist could "fix" her husband.

"I wanted to bring him in to have another person tell him 'Get yourself together,'" she divulged in a sold-out sit-down with Oprah Winfrey at Chicago's United Center that marked the launch of her book tour in November 2018.

"What I learned about myself," she concluded, "was that it's not my partner's job to make me happy. We have to make each other happy. There's a part of me that was waiting for him to do for me, and I didn't need him to do it, I needed it done. I was having arguments not about it getting done but about him doing it."

Let's just say, none of it would've gotten done, and history very well might not have been made, if not for a few twists of fate. Some of them played out in the based-on-actual-events film Southside With You, which chronicles the Obamas' first date in 1989—while other circumstances didn't exactly enhance the awkward-meet-cute-blossoms-into-a-fairy-tale narrative.

Ron Sachs-Pool/Getty Images

Harvard Law School student Barack Obama—or Barry, as some friends called him—had just started work as a summer associate at the Chicago firm Sidley & Austin. He was 27. Upon arrival, he was told to check in with 25-year-old Michelle Robinson, Harvard Law class of '88.

And by multiple accounts, including his own, he was instantly smitten.

"I had never taken the train downtown before. It was raining that day," Barack recalled of their first meeting in a video message shown during the Oprah chat. "I wasn't fully equipped with an umbrella. The bottom line is, when I walk into Michelle's office, not only am I late, I'm also kind of damp. So it's not clear whether I made the best impression."

Michelle had been tasked with mentoring the new hire—"the luckiest break of my life," then President Barack Obama said in a piece about their first date for O Magazine. She, however, had assumed—judging by his unusual name and from all the hype she'd heard—that he would be "strange and overly intellectual." 

"I remember being struck by how tall and beautiful she was," he said in O. "She, I have since learned, was pleasantly surprised to see that my nose and ears weren't quite as enormous as they looked in the photo I'd submitted for the firm directory."

7 Things About Michelle Obama's FLOTUS Style That You Didn't Know

"He sounded too good to be true," Michelle said in David Mendell's 2009 biography Obama: From Promise to Power. "I had dated a lot of brothers who had this kind of reputation coming in, so I figured he was one of those smooth brothers who could talk straight and impress people. So we had lunch, and he had this bad sport jacket and a cigarette dangling from his mouth and I thought, 'Oh, here you go. Here's this good-looking, smooth-talking guy. I've been down this road before.'"

"Later I was just shocked to find out that he really could communicate with people and he had some depth to him. He turned out to be an elite individual with strong moral values."

That was the first lady talking by then.

Scott Olson/Getty Images

Michelle told her mother, Marian Robinson, that she was going to focus on her career and put dating on the back burner. Moreover, she was concerned that the only two Black associates at the firm dating each other would look "pretty tacky," she told Mendell. (Sidley Austin partner Newton Minow told the Washington Post Magazine's Liza Mundy for her 2008 book Michelle that there were other Black lawyers at the firm, including a partner, but he could see how Michelle might have thought otherwise.)

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

"She was kind enough to take me to a few parties, and never once commented on my mismatched and decidedly unstylish wardrobe," he said in O. "I asked her out. She refused. I kept asking. She kept refusing," saying it would be inappropriate.

He even offered to quit. Finally, she agreed to go for ice cream. There's a plaque now commemorating that momentous outing at Dorchester and East 53rd Street. It reads, quoting Barack in O: "On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb. I kissed her, and it tasted like chocolate."

Scott Olson/Getty Images

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

In Southside With You, Michelle's eager suitor picked her up in an old yellow Datsun—a car the future president really did drive—after inviting her to a meeting at which, as a community organizer, he was scheduled to speak at.

First they went to the Art Institute of Chicago to check out an exhibit, they had sandwiches, she saw him speak (swoon, obviously), then they watch Spike Lee's Do the Right Thing (where they ran into a colleague and his wife) and then they had ice cream—and their first kiss.

Chip Somodevilla/Getty Images

"It was a cool date, actually," Michelle said decades later in a White House promotional video. "We spent the whole day together. He was showing me all facets of his character. He showed his cultural side, and then we took a nice long walk down Michigan Avenue."

Barack Obama's Coolest Pop Culture Moments

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.

"She had all these little facts about him," Mary Carragher, who also worked at Sidley Austin, told the paper. Carragher was one of several people who surmised that Michelle was just as smitten with Barack as he was with her. "She was just learning about him and getting to know him, and she seemed to be quite taken with him...She was just sort of amazed by him."

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

As Michelle admits in Becoming, "As soon as I allowed myself to feel anything for Barack, the feelings came rushing—a toppling blast of lust, gratitude, fulfillment, wonder."

David Hume Kennerly/Getty Images

Michelle's brother, Craig Robinson, a longtime college basketball coach who joined the Knicks as VP of player development in 2017, recalled feeling bad for Barack when his sister brought him home for dinner the first time, figuring he'd be gone after a few dates, like those who'd come before.

"He was very, very low-key," he told the Chicago Sun-Times. "I loved the way he talked about his family because it was the way we talked about our family. I was thinking: 'Nice guy. Too bad he won't last.'" Their father, Fraser Robinson III, said the same thing.

But Michelle liked him, Craig also told Mundy, because Barack "was a smart guy who didn't act like he was smarter than anybody else. That was the first thing. And he was tall and he knew how to manage my sister's personality."

Barack had to go back to Harvard at the end of the summer, but they maintained their relationship long-distance.

"Before I met Michelle, I was too immature to hold something like that together," Barack told Mendell, who notes that before Harvard, when he was working in Chicago as a community organizer, the future president had a serious girlfriend and a cat, but they had long since amiably parted ways.

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

Stars Meet the President

In his own memoirs written before he became president, Obama referred to a "compression" of girlfriends he had before meeting Michelle.

According to David Maraniss' 2012 biography Barack Obama: The Story, a woman named Genevieve Cook, whom he met in 1983 in New York after he graduated from Columbia, was "the deepest romantic relationship of his young life" at that point. That being said, when she said "I love you," he said "thank you."

Cook remembered her famous ex-boyfriend as a "virtuous daily jogger" and disciplined writer. In his own Dreams From My Father, Obama recalled telling his Kenyan sister, Auma, about Genevieve, "I pushed her away. We started to fight. We started thinking about the future, and it pressed in on our warm little world." By May 1984, they had broken up, after which Obama moved to Chicago.

In the spring of 1985, 25-year-old Barack met Sheila Miyoshi Jager, a PhD student at University of Chicago—referred to in Maraniss' book only as "the Chicago anthropologist"—through mutual friends. "This relationship ended much like the one with Genevieve, when Obama was ready to make his next career move," Maraniss wrote.

Once again, not so simple.

Brendan Smialowski-Pool/Getty Images

According to David Garrow's Rising Star: The Making of Barack Obama, which came out in 2017, Obama proposed to Jager in 1986.

Well, first they moved in together in October 1986, into a $450-a-month apartment on South Harper Avenue.

"Very sweet lady, as busy as I am, and so temperamentally well-suited," Obama wrote to a friend, per Garrow. "Not that there are no strains. I'm not really accustomed to having another person underfoot the whole time, and there are moments where I miss the solitude of a bachelor's life. On the other hand, winter's fast approaching, and it is nice to have someone to come home to after a late night's work. Compromises, compromises."

Stars Playing President

Months later, "in the winter of '86, when we visited my parents, he asked me to marry him," Jager recalled.

Influenced by her parents—her mom liked Barack but thought her too young; her dad didn't think the young man worthy—she said "'not yet.'" They stayed together, though, for almost two more years.

In early 1987, Jager told Garrow, she witnessed her boyfriend becoming "someone quite extraordinary" after starting out, to her, "quite ordinary." At the time, "he already had his sights on becoming president." At the same time, Jager (who is half white, half Japanese) said, he became "brooding, quiet, distant—and it was only then, as I recall, that he began to talk about entering politics and race became a big issue between us."

Still, Obama invited Jager to go with him to see his family in Hawaii that Christmas. By early 1988, however, Jager remembered realizing that she would never be able to marry Obama, that it wouldn't be a fit for either of their aspirations. Barack went off to Harvard that fall—but Sheila had already moved out of their Chicago apartment, supposedly after taking a peek at the journal he kept under the bed.

They stayed in touch that first year, though.

Pete Souza/White House via Getty Images

After Barack Obama graduated from law school, Michelle was still undecided when it came to their future. She asked her brother to invite her boyfriend to play pickup basketball, which he and their father considered one of the most efficient ways to get a read on someone's true character.

"Craig's opinion of Barack mattered to me and my brother knew how to read people, especially in the context of a game," Michelle wrote in Becoming.

"I realized he wasn't selfish," Craig told the New York Post in December 2018. "He wasn't greedy. He showed character on the court. He called fouls and gave up fouls. You have to trust the guys you're playing with in pickup, they'll make the right call. He did all of that. I was able to get back to her and say, 'He seems like a pretty good guy.' The best thing about it I told her is he didn't just pass me the ball because he was dating my sister."

Meanwhile, as has been mentioned over the years, Barack didn't entirely believe in the institution of marriage, even when he asked Jager to marry him.

When he and Michelle were dating long distance, she informed him of her expectations and he said that getting married didn't matter so long as they were together. 

To paraphrase Michelle: Yeah, no.

In 1991, over a fancy dinner at Gordon in Chicago, "he reached for my hand and said that as much as he loved me with his whole being, he still didn't really see the point," she recalled in Becoming. "Instantly I felt the blood rise in my cheeks...Really? We were going to do this now?"

The box with the ring arrived on a dessert plate.

Stars' Engagement Rings

Michelle Robinson married Barack Obama on Oct. 3, 1992, at Chicago's Trinity United Church of Christ. Her brother walked her down in the aisle in lieu of their late dad, who died in 1991.

"I don't think I clinched it, but I moved it in the right direction," Craig told the Post, remembering his post-game thumbs-up for his future brother-in-law. "I might've been able to derail it, but they had to clinch it."

Malia was born in 1998 and Sasha in 2001.


Becoming parents was one of the life changes that prompted a trip to counseling.

"Marriage counseling for us was one of those ways where we learned how to talk out our differences," Michelle told Robin Roberts. "I know too many young couples who struggle and think that somehow there's something wrong with them. And I want them to know that Michelle and Barack Obama, who have a phenomenal marriage and who love each other, we work on our marriage. And we get help with our marriage when we need it."

Once her husband became president, she recalled in Becoming, "Barack was now surrounded by people whose job was to treat him like a precious gem. It sometimes felt like a throwback to some lost era, when a household revolved solely around the man's needs, and it was the opposite of what I wanted our daughters to think was normal."

Meanwhile, though his presidential ambitions apparently came off loud and clear to every woman he came into contact with in the 1980s, Michelle maintained she wasn't clued in during their courtship.

Her brother Craig, however, told Liza Mundy that Barack told him at a party early on that he wanted to run for the U.S. Senate and maybe even for president one day. 

Watch: Why Michelle Obama Says She Can't Be First Lady Alone

"He probably should have said: 'Don't tell Michelle!'" Michelle told Mundy in 2007. But Craig told Vanity Fair that his sister "knew what she was getting into."

Their father worked for the city of Chicago most of his life and had been a Democratic precinct captain, which gave his daughter a preview of how political politics can get. Fraser Robinson didn't enjoy the cronyism, either.

"I didn't much appreciate politicians and therefore didn't relish the idea of my husband becoming one," Michelle wrote in her book. But, she ultimately concluded, "If Barack believed he could do something in politics, who was I to get in his way?"

Fashion at the 2017 Presidential Inauguration

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

"I've got a job, and I'm the primary caregiver for two very bright little girls," Michelle, at the time executive director of community affairs at University of Chicago Hospital, told the New Yorker in 2004 during his Senate campaign. "It's crazy. It's not realistic."

Being a politician's wife was "hard," she acknowledged. "And that's why Barack is such a grateful man."

Official White House Photo by Pete Souza

Talking to Oprah for O with her husband later that year, also before the election, Michelle said, "I would want Barack as my senator. I know this man. He is brilliant, he is decent, he is everything you'd want."

Asked the role his family played in his life, Obama said, "They're everything." 

He said, "I love this woman. We've had our rough patches..." "There were many..." Michelle agreed.

She told Winfrey, "The first people we don't want to disappoint are our kids. Barack is a great father. Even when he's away, he calls every night. People will suck you dry, and they don't think about the fact that you have two kids. He has to go to the kids' ballet events and their parent-teacher conferences. And he enjoys that."

But it was a struggle. As she writes in Becoming, when her husband was a state senator and she was a full-time working mom struggling to create family time for Barack, Malia and Sasha, she finally had to just stick to a bedtime routine and tell her spouse he either showed up or he'd miss putting the kids to bed, simple as that.

"This was my pivot point, my moment of self-arrest," she writes. "Like a climber about to slip off an icy peak, I drove my ax into the ground."

Scott Olson/Getty Images

Michelle wasn't particularly thrilled when her husband told her wanted to run for president. But she dove headfirst into the campaign and was by his side—or all over the country, at any given time, rallying support—throughout.

"My God, who can sit here and say, 'I'm ready to be president and first lady?'" she said, discussing her simultaneous reservations and unbridled support for her husband with the New York Times in 2007.

"I know Barack is something special," Michelle said. "If I didn't, I wouldn't be here." (At the same time, she confessed in Becoming, "I said yes because I loved him and had faith in what he could do. I didn't really think he could win.")

How It Feels to Be Impersonated on SNL

President Barack Obama was elected in 2008 on a wave of hope, optimism and a level of enthusiasm that hadn't been seen in generations. And once the brand of politics that his wife always had such disdain for throughout her life started to take its toll, it was the president's marriage that maintained the highest of approval ratings.

"When you're the president and the first lady, your job is not to nurture yourself," Michelle told Sarah Jessica at Barclays Center. "There's a lot of stuff I would have easily shared, but you don't want the country to have to worry about us going to marriage counseling, for example. It wasn't about us. For those eight years, it was about the service to the country."


Two terms and five years later, their lives—and the course of history—are forever changed. But at the end of the day, they're still the loving parents and devoted spouses who moved into the White House more than a decade ago. Just a couple of best friends and partners who have experienced both the pinnacle of power and the invigorating pains of starting from nothing, the headiest of highs and miserable lows, the agony of indecision and the satisfaction that comes with knowing you've made the right choice.

"We are finding each other again," Michelle told People. "We have dinners alone and chunks of time where it's just us—what we were when we started this thing: no kids, no publicity, no nothing. Just us and our dreams."

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

(Originally published Nov. 17, 2018, at 3 a.m. PT)