Barack and Michelle Obama: A Complete Relationship Timeline

Barack and Michelle Obama spent eight years in the White House, modeling a loving, happy relationship for the country and world. But their love story goes back way further than that, to their days at a Chicago law firm that eventually led to a first date, a family, and a partnership admired by millions.

Let's take a trip back in time and reminisce about one of the all-time great love stories with some of the couple's most important moments.

1989

Michelle Robinson is a 25-year-old attorney at the Chicago firm of Sidley Austin when she is tasked with showing the new guy, Barack Obama, around. “Because I went to Harvard and he went to Harvard, and the firm thought, Oh, we’ll hook these two people up,” she told ABC News. "So, you know, there was a little intrigue, but I must say after about a month, Barack, about a month in, asked me out, and I thought, No way. This is completely tacky."

“Not once, though, did I think about him as someone I’d want to date,” she wrote in her memoir, Becoming. “For one thing, I was his mentor at the firm. I’d also recently sworn off dating altogether, too consumed with work to put any effort into it.”

Eventually they do go on that date, which involves ice cream, a long walk, and a movie. In fact, a fictionalized version of the day was even turned into a movie: Southside With You.

"We clicked right away…by the end of the date, it was over…I was sold," Michelle said. Meanwhile, Barack told O, “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.”

1991

After two years of dating, Barack and Michelle get engaged on July 31, 1991.

Michelle wrote about that night in Becoming:

"As we were reaching the end of the meal, Barack smiled at me and raised the subject of marriage. 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 wrote. “Instantly, I felt the blood rise in my cheeks. It was like pushing a button in me—the kind of big blinking red button you might find in some sort of nuclear facility surrounded by warnings signs and evacuation maps. Really? We were going to do this now?"

She recalled they had a somewhat heated discussion “attorney style” about the matter for a bit. "Eventually, our waiter came around holding a dessert plate, covered by a silver lid. He slid it in front of me and lifted the cover. I was almost too miffed to even look down, but when I did, I saw a dark velvet box where the chocolate cake was supposed to be. Inside was a diamond ring,” she continued.

“Barack looked at me playfully. He'd baited me. It had all been a ruse. It took me a second to dismantle my anger and slide into joyful shock," Michelle wrote. "He'd riled me up because this was the very last time he would invoke his inane marriage argument, ever again, as long as we both should live."

Obviously, she says yes.

1992

On October 3, 1992, Barack and Michelle say, “I do.”

“You can’t tell it from this photo, but Barack woke up on our wedding day in October, 1992 with a nasty head cold,” Michelle wrote in a 2018 anniversary post. “Somehow, by the time I met him at the altar, it had miraculously disappeared and we ended up dancing almost all night. Twenty five years later, we’re still having fun, while also doing the hard work to build our partnership and support each other as individuals. I can’t imagine going on this wild ride with anybody else.”

1998

July 4, 1998, is a very big holiday for the Obamas, as they welcome their first daughter, Malia Ann Obama.

In her book, Michelle revealed that she went through IVF treatment after suffering miscarriages. “I felt like I failed because I didn't know how common miscarriages were because we don't talk about them,” she said on Good Morning America. “We sit in our own pain, thinking that somehow we’re broken.”

2001

Natasha “Sasha” Obama is born on June 10, 2001—completing the Obama foursome.

“Being a mother has been a master class in letting go,” Michelle told Meghan Markle during a British Vogue interview in 2019. “Try as we might, there’s only so much we can control. And, boy, have I tried–especially at first. As mothers, we just don’t want anything or anyone to hurt our babies. But life has other plans. Bruised knees, bumpy roads, and broken hearts are part of the deal. What’s both humbled and heartened me is seeing the resiliency of my daughters. In some ways, Malia and Sasha couldn’t be more different. One speaks freely and often; one opens up on her own terms. One shares her innermost feelings; the other is content to let you figure it out. Neither approach is better or worse, because they’ve both grown into smart, compassionate, and independent young women, fully capable of paving their own paths."

2004

The Obama family burst onto the national scene when Barack wins his campaign for an Illinois U.S. Senate seat.

He also gives a powerful keynote address at the Democratic National Convention that year, marking him as one of the party's most promising rising stars.

2007

On February 10, 2007, Barack announces he is running for president. Soon he, Michelle, and the girls were on the campaign trail.

“I said yes, though I was at the same time harboring a painful thought, one I wasn’t ready to share: I supported him in campaigning, but I also felt certain he wouldn’t make it all the way,” Michelle wrote in Becoming. “He spoke so often and so passionately of healing our country’s divisions, appealing to a set of higher ideals he believed were innate in most people. But I’d seen enough of the divisions to temper my own hopes. Barack was a black man in America, after all. I didn’t really think he could win.”

2008

This is, obviously, a big year for the Obamas. On June 3, Barack becomes the presumptive Democratic nominee for president—defeating Hillary Clinton. He officially accepts the party's nomination at the convention in August.

On November 4, 2008, he is elected the first Black president of our country. The family famously appears in front of a huge crowd in Chicago. “I would not be standing here tonight without the unyielding support of my best friend for the last 16 years, the rock of our family and the love of my life, our nation’s next first lady, Michelle Obama,” he says of his wife that night.

2009

In January the newly sworn-in couple makes the country swoon during the Inaugural Ball—especially with their first dance to “At Last,” as performed by Beyoncé.

“First of all, how good-looking is my wife?” Barack asks the crowd at one of the events.

2012

The Obamas have never been afraid to show their affection for each other, like when they get caught on the kiss cam at a basketball game in July.

Barack is reelected for a second term in November 2012. Michelle reflects on their life together at the Democratic National Convention prior to the election:

“Our life before moving to Washington was filled with simple joys…Saturdays at soccer games, Sundays at grandma’s house…and a date night for Barack and me was either dinner or a movie, because as an exhausted mom, I couldn’t stay awake for both,” she says. “And the truth is, I loved the life we had built for our girls. I deeply loved the man I had built that life with…and I didn’t want that to change if he became president. I loved Barack just the way he was. You see, even though back then Barack was a senator and a presidential candidate…to me, he was still the guy who’d picked me up for our dates in a car that was so rusted out I could actually see the pavement going by through a hole in the passenger side door. He was the guy whose proudest possession was a coffee table he’d found in a dumpster, and whose only pair of decent shoes was half a size too small.”

2017

Both Obamas campaign hard for Hillary Clinton and Tim Kaine in 2016, including Michelle's famous “When they go low, we go high” speech, but in the end Donald Trump is elected president and on January 20, 2017, is sworn in. The Obama family leaves the White House for good.

On life outside the White House, Michelle tells Oprah Winfrey, “I want to open my front door without discussing it with anyone, and I want to walk out that door and just walk. Just want to walk by myself, or with a semblance of feeling like I’m by myself. I want to sit in a yard that is not a national park. I do want to drop into Target. I want to—I do, I want to go to Target again!”

In October the couple celebrates their 25th wedding anniversary.

2018

Michelle's best-selling memoir, Becoming, is released—giving the world even greater insight into the early days of the Obama's marriage and their life in the White House. Of course, Barack is her biggest fan and supporter, even surprising her onstage at one of her events with flowers.

"This is like, you know, when Jay-Z comes out during the Beyoncé concert?… Like, 'Crazy in Love'?" he says. "It's the same thing. It's just a little sample to enhance the concert."

2019

The Obamas continue to share sweet moments on social media—like this shot of Michelle admiring Barack's painting in the National Portrait Gallery.

2020

This year has brought us even more Obama stories to love. First, the release of the Netflix documentary Becoming, about Michelle's book and tour. Then, her newest venture, The Michelle Obama Podcast. Of course, the former POTUS is her first guest.

“At the core of everything you have done politically, what I know about you as a person and one of the reasons why I fell in love with you,” Michelle says during the episode, before Barack suggests it was “just my looks.”

“You're cute, but you know. One of the reasons I fell in love with you is because you’re guided by the principle that we are each other’s brothers' and sisters' keepers," she continues. “And that's how I was raised. My values—in terms of what I think my personal obligation, Michelle Obama, is that it is not enough that I succeed on my own.”

In November 2020, an excerpt of the former president's memoir A Promised Land obtained by CNN reveals the toll that Obama's job took on his marriage. (The book will be released on November 17.)

“And yet, 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 writes. “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.

“Lying next to Michelle in the dark,” he continued, “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.”

Originally Appeared on Glamour