Barack Obama, then 28, and Michelle Robinson, then 25, met in 1989 at the law firm Sidley Austin LLP, where Robinson was assigned to be his mentor. Even though Michelle was supervising him, that didn’t stop the future President from asking her on a date. And Michelle confessed later, she was not that interested at the time. Michelle later said she changed her opinion right away during that first date. The picture above was taken in 1989, the year they met.
There’s also a biographical romantic movie called Southside with You (2016) about the beginning of their relationship and particularly about their first date. The couple got married in 1992 and since then has been together for 26 years. “Barack didn’t pledge riches, only a life that would be interesting. On that promise, he delivered,” she recalled after many years.