Why Michelle Obama's Brother Had Some Serious Doubts About Barack Obama

Michelle Obama has opened up about the struggles her marriage to Barack Obama faced during their White House years before, but her older brother, Craig Robinson, is the one spilling the real tea. 

He’s known Barack Obama years before he became President of the United States — and he didn’t think the future politician stood a chance with his younger sister. 

“Mich starts to date Barack, and we don’t know who this guy is. We’re just like, ‘Barack? Who’s got a name like Barack?’ “ Robinson joked on their sibling IMO podcast on April 16. “And I’m thinking to myself, it’s gonna last like about a month like most of your relationships did.”

The former first lady didn’t agree with Robinson’s opinion on her dating life. “That’s not true. I had many a long-term boyfriend,” she added. But her sibling wasn’t done with reminiscing about Michelle’s early love life. 

“I remember mom’s first thing was, ‘Ooo at least he’s tall.’ Because Mich was usually posting up her other boyfriends,” Robinson continued. “And I said to myself, ‘Well, it’s too bad it’s not gonna last.’ “

It took a pickup game of basketball for Robinson to give his sister’s boyfriend the official stamp of approval. “Obviously we had a great time playing. This is what I learned, aside from the fact that he’s left-handed so he couldn’t go right at all, most importantly, he was a team player,” he shared. “He fit in with the people. So, I was able to report back to you, everything was fine, and the rest was history.”

The dynamic duo met in 1988 after his first year at Harvard Law School when he took a “summer job at Sidley & Austin, a law firm in Chicago.” The 44th president had quite a vivid recollection of their summer of romance together. 

“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,” he said in a first-person essay for Oprah.com. “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.”

Michelle wasn’t that interested in dating him at first though because she was his supervisor. Barack Obama offered to quit his job, and that’s when she finally agreed to a date.

“On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb,” he recalled. “I kissed her, and it tasted like chocolate.”

Before you go, click here to see Barack & Michelle Obama’s sweetest public appearances!

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