Craig Robinson didn’t expect his sister’s new boyfriend at the time to stick around, but what happened next would help shape a lasting presidential love story.
On a recent episode of their podcast, “IMO with Michelle Obama and Craig Robinson,” the former first lady and her brother, Craig Robinson, took a nostalgic trip back to the early days of her relationship with Barack Obama — and Craig didn’t hold back, revealing just how skeptical he had been at the time.
“I’ve told this story many times about when you first started dating Barack,” Craig began. “We don’t know who this guy is. We just like, ‘Barack? Who’s got a name like Barack?'”
He didn’t think the relationship would go anywhere, brushing it off as a short-term fling. “It’s gonna last for about a month — like most of your relationships did,” he teased, prompting Michelle to fire back, “I’ve had many a long-term boyfriend.”
But Craig wasn’t convinced, replying, “I wouldn’t call those guys boyfriends.” He went on to describe the moment he and their mother first laid eyes on Barack. Sitting on the front porch waiting for Michelle to arrive, they watched as she pulled up with her new boyfriend.
“Mom’s first thing was, ‘Ooh, at least he’s tall,'” he recalled, poking fun at Michelle’s dating history. “She said, ‘At least he’s tall,’ because you were usually posting up your other boyfriends.”
Still, Craig wasn’t sold. “I said to myself, ‘Well, it’s too bad. It’s not gonna last,'” he admitted. But things shifted after Michelle asked him to take Barack to play basketball — a sort of unofficial vetting process.
Craig initially refused, saying, “No way. I am not doing your dirty work for you. If he turns out to be a bad dude, I am not going to be the one to say.”
Despite his reservations, he gave in. “I finally acquiesced,” he said. “And so we went, and obviously we had a great time playing.” That game turned out to be pivotal.
“What did you learn?” Michelle asked. Craig answered, “Aside from the fact that he is tremendously left-handed, so he couldn’t go right at all — most importantly, he was a team player. He fit in with the people.”
That quality was enough to win Craig’s approval. He reported back to Michelle that everything was fine — and the rest, as he said, was history.
While the couple’s love story began with cautious curiosity from her family, they went on to build a life and raise two children who would also capture the public’s attention in their own unique ways.
Barack and Michelle share two daughters, and online users say one looks “like her dad,” while the other is a “mini” version of her mom. Now in their 20s, Malia and Sasha Obama have earned praise from their parents.
The siblings share a deep connection that has guided them through life in the public eye. Nearly four years after their father’s presidency ended, both were in college — Malia at 22 and Sasha at 19 — when the pandemic brought them back home.
“Malia and Sasha have been with us almost continuously since March, with just a few breaks,” Barack divulged in a joint November 2020 interview.
With their daughters back home, the Obamas appreciated the unexpected time together. Barack noted that having their children join them for dinner each night, playing games, and watching movies brought them a great deal of joy.
As they grew older, the sisters became even closer. “I think part of what’s been also wonderful is seeing Malia and Sasha become such great friends,” Barack expressed.
Though three years apart, their younger days involved the usual sibling rivalries — from borrowing clothes to playful disagreements, according to their father.
The duo’s bond has only strengthened, and as young adults, they chose to share a home. In a November 2022 interview, Michelle admitted she tempered her excitement when Malia and Sasha decided to move in together, not wanting to influence their decision.
Instead, she casually responded, “Okay, well that’s interesting that you guys are going to try living together. We’ll see how it goes.” Deep down, she was grateful her daughters found comfort in each other, saying, “It’s like the one thing you want for them.”
The sisters settled into their Los Angeles apartment, decorating on a budget with finds from yard sales and Ikea. Their new chapter as roommates has brought them even closer, but their mother remains mindful of how much she shares about their lives.
