Summer 1989: First Meeting
The future President and First Lady met when Barack took a job at the Chicago law firm Sidley & Austin to help pay off his student loans. Michelle was assigned to be his advisor for his summer job.
“I remember being struck by how tall and beautiful she was,” Barack recalled of his first impression of Michelle to O, The Oprah Magazine in 2007. “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.”
July 1989: First Date
After their first meeting, it took a while for Michelle to agree to go out on a date with Barack.
“I asked her out. She refused. I kept asking. She kept refusing,” he admitted to O nearly two decades later. “‘I’m your advisor,’ she said. ‘It’s not appropriate.’ Finally, I offered to quit my job, and at last she relented.”
For their first date, the two saw went to the movies to see Spike Lee’s Do the Right Thing followed by a trip to Baskin-Robbins for a post-movie treat, where they shared their first kiss.
“He played it real smooth,” Michelle told 20/20 in 2018. “He just leaned in for a kiss and that really was it. From that kiss on we were – it was love, and he was my man.”
July 1991: A Surprise Proposal
Two years later, Barack popped the question over dinner at a Chicago restaurant, catching Michelle off-guard as she didn’t think they were on the same page about 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 in her memoir Becoming. “Instantly, I felt the blood rise in my cheeks…Really? We were doing this now?”
After all, the couple had gone back and forth debating the concept of marriage over dinner only for their conversation to come to a halt when the waiter delivered their dessert. Instead of a piece of chocolate cake sitting on Michelle’s dessert plate, however, there was a dark velvet box with a diamond ring inside.
“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,” she continued. “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.”
October 1992: Wedding Bells
More than a year after the date night proposal, Barack and Michelle tied the knot on October 3 in Chicago’s Trinity United Church of Christ.
“Barack woke up on our wedding day in October, 1992 with a nasty head cold. Somehow, by the time I met him at the altar, it had miraculously disappeared and we ended up dancing almost all night, Michelle remembered of her wedding day on Instagram in 2018. “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.”
July 1998: Stepping Into Parenthood Together
Barack and Michelle’s oldest child, Malia Obama, was born on July 4, 1998, in Chicago. While she spent much of her teen years in the White House, she later attended Harvard University, where she graduated in 2021. In addition to forging her own path in entertainment, she dropped her famous last name, opting to go by Malia Ann in the credits of her 2024 short film “The Heart.”
“I was all like, ‘You do know they’ll know who you are,’” Barack explained when asked about Malia dropping her last name on an October 2024 episode of The Pivot Podcast. “And she’s all like, ‘You know what? I want them to watch it that first time and not in any way have that association.’ So I think our daughters go out of their way to not try to leverage that.”
June 2001: Sasha is Born
Sasha Obama was born on June 10, 2001. Entering the White House at the age of 7, she was the youngest first child to move into the White House since a 2-month-old John F. Kennedy Jr. in 1961. She graduated from the University of Southern California in May 2023.
“Happy birthday to my sweet girl, Sasha! Can’t believe how quickly time has flown,” Michelle captioned a rare family portrait on Instagram for Sasha’s 24th birthday in June 2025. “I’m so proud of the woman you’ve become. Love you always!”
January 2005: Barack Becomes a U.S. Senator
After he served in the Illinois state senate, Barack won his campaign to represent Illinois in the U.S. Senate. Though, at the start of her husband’s political career, Michelle wasn’t thrilled about joining the world of politics.
“I didn’t much appreciate politicians,” she wrote in Becoming, “and therefore didn’t relish the idea of my husband becoming one.”
Despite her qualms, she supported Barack throughout his campaign and time in office.
“I think I actually realized that even while I was in the job,” he told Scott Pelley in a 60 Minutes interview in 2020. “The fact that she put up with it and forgave me is—was an act of grace that I am grateful for and I’m not sure I deserved it.”
November 2008: The Obamas Become First Family
When Barack won the presidency for the first time in 2008, he made sure to thank the country’s new First Lady.
“I would not be standing here tonight without the unyielding support of my best friend for the last 16 years,” Barack said in his victory speech, “the rock of our family, the love of my life, the nation’s next first lady, Michelle Obama.”
October 2012: Milestone Wedding Anniversary
Barack and Michelle spent their 20th anniversary apart, as Barack was in Denver, Colorado, for the first presidential debate of the 2012 election. Still, he took the time to give her a shoutout.
“There are a lot of points I want to make tonight, but the most important one is that 20 years ago I became the luckiest man on Earth because Michelle Obama agreed to marry me,” the then president said. “And so I just wanted to wish, Sweetie, you happy anniversary and let you know that a year from now we will not be celebrating it in front of 40 million people.”
Barack’s opponent, Mitt Romney even joined in on the well wishes.
“Congratulations to you, Mr. President, on your anniversary,” Mitt told Barack later during the debate. “I’m sure this was the most romantic place you could imagine here–here with me.”
The Obamas later celebrated with a dinner at Bourbon Steak in Georgetown.
November 2012: Four More Years in the White House
In 2012, Barack was re-elected president of the United States. It was not only a celebration for Barack, but also for Michelle, who helped her husband in more ways than one throughout his campaign.
“Obviously I couldn’t have done anything without Michelle,” Barack gushed on The Oprah Winfrey Show in 2011. “Not only has she been a great first lady, she is just my rock. I count on her in so many ways every single day.”
January 2017: Leaving the White House
In his last speech as president, Barack made sure to give a heartfelt note of gratitude to his wife.
“For the past 25 years, you have not only been my wife and mother of my children, you have been my best friend,” Barack said in his farewell address in 2017. “You took on a role you didn’t ask for and you made it your own, with grace and with grit and with style and good humor…So, you have made me proud. And you have made the country proud.”
November 2020: A Glimpse into Life Outside of the White House
Since 2017, the Obamas have appreciated life outside of the political spotlight—which the Audacity of Hope author admitted has been a breath of fresh air for his wife.
“[Mrs. Obama] has been more relaxed and more joyful since we left office,” Barack told People in 2020. “That allowed us to just enjoy the deep love that comes with a marriage this long. But also to be friends again.”
October 2022: 30th Wedding Anniversary
The couple posted sweet tributes for each other on social media to celebrate 30 years of marriage.
“Happy anniversary to the man I love!” Michelle wrote on X, formally known as Twitter. “These last 20 years have been an adventure, and I’m grateful to have you by my side. Here’s to a lifetime together. I love you @BarackObama.”
And he quickly returned the favor.
“After 30 years, I’m not sure why you look exactly the same and I don’t,” Barack joked on Instagram. “I do know that I won the lottery that day–that I couldn’t have asked for a better life partner. Happy anniversary, sweetheart!”
August 2024: Democratic National Convention Date Night
After Michelle’s 20-minute speech at the 2024 DNC, she introduced her husband, calling him “the love of my life.” The two shared a hug, with Barack hyping his wife up to the audience.
“I’m feeling fired up,” Barack told the crowd, “even if I’m the only person stupid enough to speak after Michelle Obama.”