Though she was his mentor, that didn't stop the future President from asking Robinson on a date. She said she was not so keen at the time.
"Barack, about a month in, asked me out, and I thought 'No way. This is completely tacky,'" she told ABC News.
But eventually she relented, and the pair went on a date. They started by having lunch at the Art Institute of Chicago, taking a stroll, then ending up going to see the Spike Lee film "Do The Right Thing."
"He showed all the sides — he was hip, cutting edge, cultural, sensitive. The fountain – nice touch. The walk — patient," Michelle later told The Telegraph.
"Take tips, gentlemen," Barack added, smiling.
The date was eventually immortalized in the film "Southside With You."