Everything Barack Obama Shared About His Family in His New Book, From Inside Jokes to Those Lonely Nights

Yes, Barack Obama's third memoir—his first since his presidency—is filled with plenty of choice details about his eight years in the White House, but he also served up plenty of personal details.

By Sarah Grossbart Nov 18, 2020 3:00 PMTags
Watch: Michelle Obama Opens Up About Miscarriage & Marriage Counseling

You'd be forgiven for thinking you know every last detail about former president Barack Obama's life. 

Between the memoirs (his pre-presidency books Dreams from My Father and The Audacity of Hope and Michelle Obama's 2018 read, Becoming), the high-profile interviews and eight years living under the brightest spotlight that exists in the Western hemisphere, one would think we'd eagerly consumed every last anecdote out there about the onetime commander-in-chief, his even more popular bride and their daughters Malia Obama, 22, and Sasha Obama, 19. (Especially now that the world's most famous elementary schoolers are somehow full-on adults with access to TikTok and friends with bands to promote.)

And yet Barack—smack dab in the middle of his second act as a Netflix employee and hype man for his second-in-command, President-elect Joe Biden—left a little juice for A Promised Land, his third memoir in 25 years. 

To say we were shocked by his confession that his enviable marriage was rocked by his 2009-2017 stint in the White House is a severe understatement. But here was the Harvard grad admitting that all that scrutiny was a lot for even the most rock-solid of unions to withstand. 

Malia Obama and Sasha Obama Over the Years

"Despite Michelle's success and popularity, I continued to sense an undercurrent of tension in her, subtle but constant, like the faint thrum of a hidden machine," he wrote of how holding the most high-profile of gigs affected their marriage. "It was as if, confined as we were within the walls of the White House, all her previous sources of frustration became more concentrated, more vivid, whether it was my round the clock absorption with work, or the way politics exposed our family to scrutiny and attacks, or the tendency of even friends and family members to treat her role as secondary in importance."

There were more than a few nights, he continued, in which "lying next to Michelle in the dark, I'd think about those days when everything between us felt lighter, when her smile was more constant and our love less encumbered, and my heart would suddenly tighten at the thought that those days might not return."

Pablo Martinez Monsivais/AP/Shutterstock

Though, as evidenced by their recent anniversary tweets, Barack crediting his First Lady with making him "a better husband, a better father, and a better human," and Michelle responding that she was "so grateful to have him as a partner through everything life throws at us," they've returned back to their loved-up former selves. 

While every page of Barack's Nov. 17 release is worthy of scrutiny—the politician digging deep into an adolescence spent grappling with his racial identity, his meteoric rise through politics and the divisiveness that has seeped into Washington, D.C.—we here at E! News are most interested in dissecting the bits about his accomplished, tight-knit, impossibly photogenic fam. Really what else did you expect? 

So starting with that first meeting that saw the bold law student hit on his boss to the habit that drove her mad, here are the reveals that kept us hooked through all 768 pages.  

His Lack of Game

While not technically about his romance with Michelle Obama, one early passage clued us into the man Barack Obama was before, as a first year law student, he pestered his boss at Chicago's Sidley & Austin to join him for some Baskin Robbins

"Looking back it's embarrassing to recognize the degree to which my intellectual curiosity those first two years of college paralleled the interests of various women I was attempting to get to know," he shared of his days at Los Angeles' Occidental College, where he matriculated before transferring to Columbia University in 1981, "[KarlMarx and [HerbertMarcuse, so I had something to say to the long-legged socialist who lived in my dorm; [FrantzFanon and Gwendolyn Brooks for the smooth-skinned sociology major who never gave me a second look; [MichelFoucault and [ChristianWoolf for the ethereal bisexual who wore mostly black." 

As a strategy, he wrote, his "pseudo-intellectualism" was largely flawed. "I found myself in a series of affectionate but chaste friendships," he noted. "Still these halting efforts served a purpose: Something approaching a worldview took shape in my mind."

Infatuated at First Sight

So consider him more well-rounded, when, as a year one at Harvard Law School, he decided to hit on Michelle Lavaughn Robinson, the 25-year-old associate assigned to look after him during his summer internship. "She was tall, beautiful, funny, outgoing, generous and wickedly smart—and I was smitten almost from the second I saw her," he wrote. Michelle's responsibilities included making "sure I knew where the office photocopier was and that I generally felt welcome," which meant they attended more than a few lunches together, he continued, "which allowed us to sit and talk—at first about our jobs and eventually about everything else." 

Their Early Courtship

As Barack finished up schooling, the two navigated long-distance. "Over the course of the next couple of years, during school breaks and when Michelle came to Harvard as part of the Sidley recruiting team, the two of us went out to dinner and took long walks along the Charles River, talking about movies and family and places in the world we wanted to see," he wrote.

When her father passed away unexpectedly, succumbing from complications related to multiple sclerosis, "I flew out to be with her," he continued. She, in turn, was by his side when he learned his grandfather was diagnosed with advanced prostate cancer. "In other words," he shared, "we became friends as well as lovers."

With his big ambitions and belief that he could truly change the world, Barack was aware he was unlike any guy Michelle had been with before. "I imagine her just before we met, very much the young professional, tailored and crisp, focused on her career and doing things the way they're supposed to be done, with no time for nonsense" he shared. "And then this strange guy from Hawaii with a scruffy wardrobe and crazy dreams wanders into her life. That was part of my appeal, she would tell me, how different I was from the guys she'd grown up with, the men she had dated." 

A Formidable Foe

Michelle was also "an original," as he put it. "I knew nobody quite like her." Two bold personalities, they often found themselves at odds. "In those early years of our courtship, our arguments could be fierce," he shared. "As cocksure as I could be, she never gave ground." 

It was the reason her older brother Craig Robinson—now vice president of player and organizational development for the New York Knicks—used to joke that "Miche" might never find a worthy adversary "because she was too tough—no guy could keep up with her," said Barack. "The weird thing was, I liked that about her, how she constantly challenged me and kept me honest." 

Knowing She Was "The One"

As Barack was wrapping up his law school studies, he realized he was ready to embark on another new adventure. "I was starting to think I might ask her to marry me," he revealed. "For Michelle, marriage was a given—the organic next step in a relationship as serious as ours. 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." 

And yet on that day in 1991 he found himself kneeling over dessert, asking Michelle to be his bride.

"Life with me promised Michelle something else, those things that she saw she had missed as a child," he explained. "Adventure. Travel. A breaking of constraints. Just as her roots in Chicago—her big extended family, her common sense, her desire to be a good mom above all else—promised an anchor that I'd been missing for much of my youth. We didn't just love each other and make each other laugh and share the same basic values—there was symmetry there, the way we complemented each other. We could have each other's back, guard each other's blind spots. We could be a team." 

Having the Talk

That partnership meant Barack soon had to broach another serious topic with his bride-to-be. "As law school was coming to an end, I told Michelle of my plan," he said. "I wouldn't clerk. instead, I'd move back to Chicago, try to keep my hand in community work while also practicing law at a small firm that specialized in civil rights. If a good opportunity presented itself, I said, I could even see myself running for office." 

Having already watched him do his thing during an organizing workshop at his friend's South Side community center, "None of this came as a surprise to her," he wrote. "She trusted me, she said, to do what I believed was right." 

She was rightfully cautious, however. "'I need to tell you, Barack,' she said, 'I think what you want to do is really hard. I mean, I wish I had your optimism. Sometimes I do. But people can be so selfish and just plain ignorant. I think a lot of people don't want to be bothered. And I think politics seems like it's full of people willing to do anything for power, who just think about themselves. Especially in Chicago. I'm not sure you'll ever change that.'"

His response was pretty much what you'd expect from the man who coined the phrase, "Yes we can" and the overarching idea of hope. "'I can try, can't I?' I said with a smile. 'What's the point of having a fancy law degree if you can't take some risks? If it doesn't work, it doesn't work. I'll be okay. We'll be okay.'"

Newlywed Life

A year after Barack's dinner date proposal, the two were wed on Oct. 3, 1992 at Trinity United Church of Christ "with more than 300 of our friends, colleagues and family members crammed happily into the pew," he detailed. "The service was officiated by the church's pastor, Reverend Jeremiah A. Wright Jr., whom I'd come to know and admire during my organizing days. We were joyful. Our future together was officially beginning." 

After a honeymoon along the California coast, Barack accepted a position teaching at the University of Chicago Law School, wrote his first book and took a job at a small civil rights firm. Michelle left corporate law behind, spending a little more than a year in the City of Chicago's Department of Planning and Development before moving on to direct Public Allies, a nonprofit youth leadership program. "Both of us enjoyed our jobs and the people we worked with, and as time went on, we got involved with various civic and philanthropic efforts," Barack wrote. "We took in ball games and concerts and shared dinners with a widening circle of friends." 

Buying a "modest but cozy condo" near her brother in Hyde Park and just 15 minutes from Michelle's family home, they'd often visit for barbecues, feasting on fried chicken as nephews and nieces ran about. "Driving home in the twilight," he shared, "Michell and I sometimes talked about having kids of our own—what they might be like, or how many, and what about a dog?—and imagined all the things we'd do as a family. A normal life. A productive, happy life. It should have been enough." 

Almost Walking Away

Within years, though, it became clear that Barack was destined for much, much more. Elected to the Illinois Senate in 1996, he took a stab at the U.S. House of Representatives in 2000, losing in the democratic primary. Re-elected to the state senate in 2002, he once again flirted with a role in the federal government, entering into the 2004 race for the U.S. Senate. 

"With Michelle, I didn't sugarcoat the amount of time I'd be away," he wrote of his campaign. "But this was it, I promised, up or out; if I lost this one, we were done with politics for good." He emerged victorious, capturing 70 percent of the vote and was sworn in on Jan. 3, 2005. 

Michelle's Hesitance

Having made a splash speaking at the 2004 Democratic National Convention, it soon became clear the junior senator from Illinois had a real shot at claiming the highest seat in the land. 

He just had to convince Michelle, who implored him not to run for president in that 2008 election so they could have a chance at a more stable life. "I couldn't claim I was indispensable to the cause of freedom and justice, or deny responsibility for the burden I'd be placing on my family," he shared. "Circumstances may have opened the door to a presidential race, but nothing during these months had prevented me from closing it. I could easily close the door still. And the fact that I hadn't, that instead I had allowed the door to open wider, was all Michelle needed to know. If one of the qualifications of running for the most powerful office in the world was megalomania, it appeared I was passing the test."

At one point, Michelle asked what was driving his run. His response, he shared, was all about setting an example for those like him, saying, "I know that the day I raise my right hand and take the oath to be president of the United States, the world will start looking at America differently. I know that kids all around this country—Black kids, Hispanic kids, kids who don't fit in—they'll see themselves differently, too, their horizons lifted, their possibilities expanded. And that alone...that would be worth it."

Settling In

Surprising precisely no one, Michelle soared in her new role as First Lady. As Barack recalled, she helped their daughters Malia Obama and Sasha Obama (then just 10 and 7) adjust to their new city and school and "quickly made a new circle of friends, many of them the mothers of Malia's and Sasha's classmates," he said, "and she had a little more flexibility than I did to leave the White House completely unnoticed." 

Her initiatives, he continued, were "well received," including her Let's Move! campaign to combat childhood obesity and Joining Forces, a project with Second Lady Jill Biden to support military families. "Whenever she appeared in public, whether it was visiting a public school classroom or trading good-natured barbs with late-night television hosts, people seemed irresistibly drawn to her genuineness and warmth, her smile and quick wit," he added. "In fact, it was fair to say that, unlike me, she had not missed a step or hit a false note from the moment we'd arrived in Washington." 

Constant House Parties

Elevated to the highest of social statuses, the duo "began hosting small dinner parties in the residence every few months," he said, "inviting artists, writers, scholars, business leaders and others whose paths we'd crossed and wanted to know better."

On the guest list: Toni Morrison ("at once regal and mischievous") and Meryl Streep (who leaned over "to softly recite in Mandarin the lyrics to a song about clouds that she's learned for a part years ago"). Their high-profile guests would often stay "until well past midnight," he revealed, "full of wine-fueled conversations."  

The House Where It Happened

But the best perk, he said, were the concerts Michelle arranged as part of her effort to "make the White House more welcoming—a 'People's House.'" Teaming with public television, she booked everyone from Justin Timberlake and Jennifer Lopez to Stevie Wonder and B.B. King to host a day full of music workshops with local youths followed by an evening concert. 

The highlights were plentiful (Bob Dylan tackling a stripped-down rendition of his hit "The Times They Are a-Changin'"; Paul McCartney serenading the First Lady with the Beatles' "Michelle"), but one in particular stood out. "I remember a young playwright of Puerto Rican descent named Lin-Manuel Miranda, who told us in the photo line before an evening of poetry, music and the spoken word that he planned to debut the first song of what he hoped would be a hip-hop musical on the life of America's first Treasury secretary Alexander Hamilton," he wrote. "We were politely encouraging but secretly skeptical, until he got up onstage and started dropping beats and the audience went absolutely nuts."

Behind Close Doors

Their eight years were filled with plenty of more normal pleasures, as well. "Evenings when the two of us snuggled under a blanket to watch a show on TV," he detailed, "Sunday afternoons when we got down on the carpet with the girls and Bo and the entire second floor of the residence filled up with laughter." Even their morning breakfasts, when she would make cracks about his daily briefing binder: "Michelle called it 'The Death, Destruction, and Horrible Things Book.'" 

But more often than not, his job saw them spending their days largely apart. "Michelle retired to her study once dinner was done, while I headed down the long hall to the Treaty Room," he recalled of their standing operating procedure. "By the time I was finished with work, she'd already be asleep. I'd undress, brush my teeth and slip under the covers, careful not to wake her." 

Loss of Control

Ultimately, though, Michelle's chief complaint had little to do with the long nights or even his five-cigarette-a-day habit, a vice he called "a chronic source of tension throughout my marriage." Rather, he explained, it was the realization that she no longer had a real say in how the days, months and years ahead of them would play out. 

"The White House reminded her daily that fundamental aspects of her life were no longer entirely within her control," he explained. "Who we spent time with, where we went on vacation, where we'd be living after the 2012 election, even the safety of her family—all of it was at some level subject to how well I performed at my job, or what the West Wing staff did or didn't do, or the whims of the voters, or the press corps, or [then-Senate Minority Leader] Mitch McConnell, or the jobs numbers, or some completely unanticipated event occurring on the other side of the planet. Nothing was fixed anymore. Not even close." 

Still, he continued, "Michelle rarely shared such feelings directly with me. She knew the load I was carrying and saw no point in adding to it; for the foreseeable future, at least, there wasn't much I could do to change our circumstances. And maybe she stopped talking because she knew I'd try to reason away her fears, or try to placate her in some inconsequential way, or imply that all she needed was a change in attitude." 

What's Next? 

Despite his protestations that all was fine, Barack copped to his share of sleepless nights when he worried about how all these stressors might impact his marriage. "I know that it was around this time that I started having a recurring dream," he wrote.

In it, he found himself in an indistinguishable neighborhood, sun shining as he strolled along "when suddenly I realize that no one recognizes me," he described. "My security detail is gone. There's nowhere I have to be. My choices have no consequence. I wander into a corner store and buy a bottle of water or iced tea, making small talk with the person behind the counter. I settle down on a nearby bench, pop open the cap on my drink, take a sip and just watch the world passing by. I feel like I've won the lottery."

—Reporting by Beth Sobol