First Forever: How The First Family Met & Had The Longest First Date Ever

(photo courtesy of YouTube screenshot)

(photo courtesy of YouTube screenshot)

In the late 80’s, a beautiful, hard-working, family-oriented Michelle Robinson told her mother she was going to concentrate on her law career and not worry about dating. She was 25 and had just finished her first year as an associate at Sidley & Austin, a corporate law firm in her home town of Chicago. Not long after, the firm assigned her to mentor a summer associate named Barack Obama.

Barack O-what? At least that’s what many people thought when they first heard his name. Now, you can’t go anywhere in the world without knowing the leader of the Free World’s name and his wife’s: Barack and Michelle Obama. Now, there’s even a movie about the First couple and how they met called, “Southside With You” which hits theaters on Friday, August 26th.

The backstory surrounding their courtship is that the President and First Lady had one of the longest first dates ever, which set the backdrop for the beautiful First Family we see today. But truth be told, it was NOT love at first sight.

MUST SEE: 24 Years Of Marriage For The Obamas, 24 Times They Fell In Love

During the summer of 1988, there was a lot of buzz about this 27-year-old prodigy from Harvard Law School. Sidley & Austin Law didn’t usually hire first-year law students as summer associates, so Barack’s arrival was pretty noteworthy. Martha Minow, a law professor at Harvard, told her father, Newton Minow, a high-ranking partner at Sidley, that Barack was possibly the most gifted student that she had ever taught. Michelle, who’d graduated from Harvard Law herself in 1988, felt annoyed by all the talk about this new associate. Why were people surprised that a black man might be smart, articulate and capable?

(photo credit:

(photo credit:

His name struck her as odd too, as did the fact that he had grown up in Hawaii. She assumed a few things about the future president based on these rare facts.

“He sounded too good to be true,” she told David Mendell, author of “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 these 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.'”

TAKE A LOOK: President Obama Says He Loves His ‘Tall Black Wife With Gorgeous Curves’

But when Barack met Michelle, he didn’t assume anything — except that he would get a first date. In his own words, here’s what President Obama told Oprah about their first date:

“I met Michelle in 1988, after my first year of law school, when I took a summer job at Sidley & Austin, a law firm in Chicago. A year earlier I had been working as a community organizer in some of Chicago’s poorest neighborhoods, and I struggled with the decision to go to a large firm. But with student loans mounting, the three months of salary they offered wasn’t something I could pass up.”

“Michelle worked at Sidley, too, and, in the luckiest break of my life, was assigned to be my adviser, charged with helping me learn the ropes. I remember being struck by how tall and beautiful she was. 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.”

“Over the next several weeks, we saw a lot of each other at work. She was kind enough to take me to a few parties, and never once commented on my mismatched and decidedly unstylish wardrobe.”

“I asked her out. She refused. I kept asking. She kept refusing.”

“‘I’m your adviser,'”she said. ‘It’s not appropriate.’ Finally, I offered to quit my job, and at last she relented. 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.”


“I had known those student loans were going to get me a great education, but I had no idea…