We all judge our siblings’ significant others at first. And if you’re the big brother, multiply that by ten. So when Michelle Obama introduced her then-boyfriend Barack Obama to her brother Craig Robinson, the future First Lady might’ve been swooning, but Craig was not sold.
On the April 16 episode of “Michelle Obama: The Light Podcast” (which she co-hosts with her brother), the former First Lady, 61, and her older bro, Craig, 62, took us down memory lane, which was hilarious. Because long before he was the President of the United States or America’s Cool Dad, Barack was just the new guy Michelle was dating. And Craig had opinions.
The brother-in-law’s glow-up no one saw coming
“Mich starts to date Barack, and we don’t know who this guy is,” Craig said, teasing the moment his sister brought home someone new. “We’re just like, ‘Barack? Who’s got a name like Barack?”
He wasn’t feeling super confident about the longevity of the relationship either. “I’m thinking to myself, it’s gonna last like about a month, like most of your relationships did,” he joked.
Michelle Obama, naturally, did not let that one slide. “That’s not true. I had many a longterm boyfriend,” she clapped back.
However, when it came to Michelle’s dating track record, the two siblings couldn’t agree, and honestly, that’s part of the fun. However, they did agree that their mom had an eye for height.
“I remember mom’s first thing was, ‘Ooh, at least he’s tall,'” Craig recalled, pointing out that Michelle, who’s 5’11”, wasn’t exactly bringing home short kings before. “And I said to myself, ‘Well, it’s too bad it’s not gonna last.'”
Barack’s make-or-break moment
But Craig wasn’t going to let just anyone date his little sister. Like any protective older sibling, he had to test this guy out. Enter: the ultimate character check, pickup basketball.
Craig explained that their dad once told him, “You can learn a lot about a person by how they play a game of pickup.” So when Michelle asked Craig to invite Barack to play, he kept a close eye.
“Obviously we had a great time playing. Aside from the fact that he’s left-handed and couldn’t go right at all,” Craig joked, “most importantly, he was a team player. He fit in with the people.” It was enough for Craig to give Barack the all-clear. “So I was able to report back to you, everything was fine and the rest was history.”
And by history, he means presidential history. Barack and Michelle tied the knot in October 1992 and went on to raise daughters Malia, now 26, and Sasha, 23.
No more pickup games in the White House
It turns out that Barack’s love of pickup didn’t quite survive the presidency. Michelle revealed that he had to hang up his court shoes after one painful incident in the White House.
“He needed, like, 30-something stitches,” she said, explaining how Barack split his lip playing a game. “He had some major speech on Monday. I was like, ‘This is what I’m saying. You’re playing like you’re 10, and now your lip is split.'”
Still got the game, just not on the court
While he may not be dunking anymore, Barack’s romance game is very much alive. This past Valentine’s Day, he dropped a heart-melter on Instagram: “Thirty-two years together and you still take my breath away. Happy Valentine’s Day, @MichelleObama!”
Michelle has also been super open about embracing her independence lately, which unfortunately sparked a round of ridiculous rumors that she and Barack were calling it quits.
“That’s the thing that we as women struggle with — disappointing people,” she told Sophia Bush on the “Work in Progress” podcast earlier this month. “So much so that this year people couldn’t even fathom that I was making a choice for myself… they had to assume that my husband and I are divorcing.”
But he’s just a grown woman making moves. And if anything, it just proves that love, independence, and self-respect can all go hand in hand.
So yeah, Craig may have been skeptical of a guy named “Barack” all those years ago. But now? He’s not just family; he’s the brother-in-law who made history.
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