Michelle Obama's Independent Streak, and Her Romance With Barack

Oct. 3, 2008— -- Growing up on the South Side of Chicago, Michelle Obama learned the value of a strong work ethic from her father, Fraser Robinson.

He had multiple sclerosis but managed to go to work every day at the city's water-filtration department where he worked as a pump operator. Her mother, Marion, stayed home to raise Michelle and her big brother, Craig.

Click HERE to watch Diane Sawyer's "Portrait of a President"

Today, Craig Robinson suggests that their family dynamic was comparable to the Cleavers in the 1950s sitcom "Leave It to Beaver." He said their parents taught them to have high standards, and to have respect for themselves and others.

"We always said that peer pressure didn't mean anything if you had Fraser and Marion Robinson pressure," he said. "And a black version of the Cleavers, no less."

The Robinsons lived in a townhouse, in a small one-bedroom apartment on the top floor.

"You really didn't know how poor you were," Robinson said.

Meeting Barack Obama

Brother and sister slept in the living room with a makeshift wall dividing them. The two were close and even looked alike, often mistaken for twins. Her brother made sure to look out for his younger sister, especially when it came to the men she dated.

By the late 1980s, Michelle Robinson was holding out for a guy as good as her dad.

"My sister never had too many long-term boyfriends," Robinson said.

Michelle met Barack Obama when she was a 25-year-old lawyer at a corporate law firm, fresh out of Harvard Law School. Barack, then 28 years old, was a summer associate finishing law school. She was assigned to be his adviser.

"Because I went to Harvard and he went to Harvard, and the firm thought, 'Oh, we'll hook these two people up,'" Michelle Obama said. "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."

He persisted, and she finally relented, agreeing to a first date at a museum, followed by a movie and ice cream. She eventually brought him home to meet her family. They liked him, but her brother wasn't hopeful.

"We all thought, it's too bad. That guy's going to be out in a minute," Robinson said.

Craig, who is two years older than Michelle, acted as a kind of undercover agent during Barack's visit, subjecting him to a secret character test during a game of basketball.

"You can really tell selfishness on the basketball court," Robinson said. "You know, he wasn't selfish."

'I Do What I Think Is Best'

Barack Obama had won big marks, but Michelle wasn't swayed one way or the other.

"Ultimately, I do what I think is best," she said. "Now it sort of made me look at him a little more closely. Because if he were just a jerk, which is something that you can see in how somebody behaves on a team, that would give me some pause. But, you know, if you were just not a good player, I probably would've still married him."

Barack Obama had several girlfriends throughout his college years. His best pickup strategy? Being the smartest guy at the coffee shop. But he has never looked back. He says he can't imagine being married to anyone other than Michelle. In his campaign speeches he has advised young men to "marry a woman who's superior to you," a feat Barack Obama says he met.

"I mean, she's so ... part of me. I look at our daughters. I think everybody feels this at a certain point. I can't imagine having daughters that look any different from Malia and Sasha. And they are perfect," he said with a laugh. "So, obviously it was destiny."

He and Michelle had been dating for two years and had talked about marriage but hadn't made any decisions. Then, one day, Barack Obama proposed.

"We were at a restaurant having dinner to celebrate the fact that he had finished the bar," Michelle, 44, remembered. "And that was supposedly the reason. And then the waiter came over with the dessert and a tray. And there was the ring. And I was completely shocked."

Barack Obama didn't wax eloquent during the proposal, instead he simply asked, "Will you marry me?"

Michelle replied with enthusiasm: "Yes!"

And the rest, as they say, is history.

Click HERE to watch Diane Sawyer's "Portrait of a President"