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In June 1989, Barack Obama (Parker Sawyers), a young associate at the Chicago law firm of Sidley Austin, meets Michelle Robinson (Tika Sumpter). A lawyer herself, she's assigned to be Obama's advisor at the firm.

Although she declines his initial requests for a date, Michelle finally accepts by late summer. On their first date, they visit the Art Institute of Chicago, view a screening of Spike Lee's movie Do the Right Thing, and have their first kiss outside an ice cream parlor.