Barack Still Tucks Michelle In at Night and More Sweet Details of the Obama's 27-Year Love Story

Get to know the real-life story behind Southside with You

Photo: Courtesy Obama for America.

In September, the highly anticipated Obama romance film, Southside with You hit theaters, giving audiences a deeper look at how our former POTUS and FLOTUS met and fell in love.

And though their first date was pretty memorable, the rest of their love story is even more romantic – down to the fact that, in the White House, he still tucks her into bed every night. (We’ll get to that!)

Because of that, they’re one of the couples PEOPLE is celebrating on People Icons: Celebrity Love Stories, the first episode in a new limited series between ABC News and PEOPLE that premieres Tuesday at 10 p.m. ET on ABC.

Barack Obama and Michelle Robinson met while working at the Chicago law firm Sidley Austin, when Barack was working as a summer associate and Michelle was his adviser.

At first, Michelle said she expected her advisee, then a Harvard Law student, to be “nerdy, strange, off-putting.”

But he surprised her.

“I was charmed,” she told Chicago Magazine. “I was pleasantly surprised by who he turned out to be.”

And his looks didn’t hurt.

“He was cuter than I thought he’d be,” she told CNN.

Their first date, back in 1989, – the subject of Southside with You – was a long one. “We spent the whole day together,” Michelle said. They went to the Art Institute of Chicago, had lunch in the museum’s courtyard, had a drink on the 99th floor of the John Hancock building, saw Spike Lee’s Do the Right Thing and took a long walk down Michigan Avenue.

“He showed all the sides,” she said in a video. “He was hip. Cultural. Sensitive. The fountain, nice touch. The walk, sensitive.”

“Take tips, gentlemen,” he added.

He impressed her family, too. When Michelle brought Barack home to meet her mother, Marian Robinson, she got a good vibe from the future president.

“He was very tall and strong, because she’s strong,” Robinson told PEOPLE in 2007. “And, you know, it just seemed like a good match. I just think he’s a nice person and I just think she felt like he was a nice intelligent young man and she said he had a good sense of humor.”

Michelle’s brother, Craig Robinson, agreed.

“It wasn’t easy to pass the approval test in the Robinson household,” he wrote in his 2010 book, A Game of Character. “Although I have to admit that the first time we met Barack, he couldn’t have made a better impression.”

Clearly, Barack charmed the object of his affections, too: He took her to church basements where she saw him speak, and got a glimpse of the politician he’d grow to be.

“He was able to articulate a vision that resonated with people, that was real,” she said. “And right then and there, I decided this guy was special. The authenticity you see is real, and that’s why I fell in love with him.”

They were together through four years of ups and downs (including the 1991 death of Michelle’s father) before he proposed in 1991, at the now-closed Gordon’s restaurant in Chicago, placing a ring next to the dessert – just after Michelle was telling him to get serious about their relationship.

“I don’t think I even ate it,” she said. “I was so shocked and sort of a little embarrassed because he did sort of shut me up.”

Two years after they wed, and two decades before Barack announced his candidacy for president, the couple was profiled in the New Yorker in the story “A Couple in Chicago,” part of a series on various couples across the United States (talk about foresight).

Four years into their marriage, Barack was still smitten with Michelle, and the sides of her not everyone else got to see.

“Michelle is a tremendously strong person, and has a very strong sense of herself and who she is and where she comes from,” he said. “But I also think in her eyes you can see a trace of vulnerability that most people don’t know, because when she’s walking through the world she is this tall, beautiful, confident woman.”

And even in 1996, Michelle knew a political career could be on the horizon for her husband, but was worried about how he’d handle it.

RELATED VIDEO: What Was Barack and Michelle Obama’s First Date Like!? ‘Southside With You’ Gives Us an Inside Look!

“There is a little tension with that,” she said. “I’m very wary of politics. I think he’s too much of a good guy for the kind of brutality, the skepticism.”

Michelle also told the New Yorker about how Barack had changed her.

“Barack has helped me loosen up and feel comfortable with taking risks, not doing things the traditional way and sort of testing it out, because that is how he grew up,” she said.

Michelle was right: Barack was elected to the Illinois State Senate in 1996, representing neighborhoods on Chicago’s South Side. He was reelected in 1998 and in 2002. In 2000, he had a failed attempt at winning a seat in the U.S. House of Representatives.

It was a busy few years for the family at home, too: In 1998, the couple welcomed their first daughter, Malia, and in 2001, their second, Natasha, who goes by Sasha.

It was just a few years after Sasha’s birth that Barack once again set his eyes on the national stage: He ran for the junior U.S. Senate seat in Illinois, and beat the Republican candidate, Alan Keys, with a whooping 70 percent of the vote.

It didn’t take long for rumors to start buzzing about the young, charismatic senator from Illinois – and his potential plans for a presidential run in 2008.

And when he did run, the future first couple – and their relationship – shot into the public eye. Michelle quickly showed that she was not a stand-back-in-the-shadows sort of woman.

“You want to know how Barack prepares for a debate?” she asked Jay Leno during a pre-election interview. “He hangs out with me.”

Even in those early days of their life in the spotlight, we saw glimpses of the romance between Barack and Michelle. In the thick of his presidential campaign, just a month before Election Day, he insisted on returning home to Chicago to take his wife out to dinner for their 16th wedding anniversary. During an interview with Barbara Walters, Barack stopped Michelle mid-question to let her know she had a smudge of lipstick on her teeth.

As we all know, the Obamas went on to win the White House, becoming the first ever African-American president and first lady in U.S. history. It came with some added perks for their family, too: Michelle said having Barack’s office so close by meant she and their daughters saw him more than ever before.

“The time that we’ve had here at the White House, we’ve spent more time together on a daily basis as a family,” she told PEOPLE in 2012. “During most of our marriage where he was in Springfield, and I was in Chicago; he was in Washington, I was in Chicago. So now we live above the store.”

Even now, after 24 years of marriage, the romance hasn’t waned for the first couple: Despite their busy schedules, they still manage to exercise with one another, have dinner as a family and walk the dogs.

And they’ve never been shy about showing their affection for one another, from a moment on the “kiss cam” at a U.S. men’s basketball game and their loving embrace after he was reelected in 2012 (an image that became one of the most retweeted of all time) to the quiet moments of intimacy throughout his presidency, captured by the White House photographers.

Michelle even told PEOPLE in 2012 that Barack still “tucks” her into at night.

“We call it tucking,” she said. “He’ll come and say good night and turn the lights out and give me a kiss, and we’ll talk. But I do call it – he’s like, ready to be tucked? I’m like, yes, I am.”

“That’s usually a time when we can check in if I’m not really already asleep,” she laughed. “Sometimes I am.”

Michelle, Barack said, doesn’t just give him love, but brings him back down to earth when the pressure gets high, or the job gets (even more) intense.

“She sees the humor in situations where I might be taking myself too seriously,” he’s said. “She always knocks me down a peg, and it’s important.”

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