The Ivy League-educated former first lady, mother of two and now best-selling author was met with thunderous applause as she walked onstage to promote her recently released memoir, "Becoming".
"That whole, 'so you can have it all.' Nope, not at the same time", she said to the audience.
"It's not always enough to lean in, because that s-t doesn't work all the time", Obama said.
The writer and cultural commentator Touré was there, and tweeted that the audience "freaked out" when Obama used the curse word - and that the former first lady herself said she "forgot where she was for a moment".
"We all have to find the people who believe in us", she said. Before then, she was a lawyer - likely never imagining a life as First Lady. "And I'm like, duh, marriage is hard, it is hard".
Both Obama and Markle both share a special interest in women and girls and equality.
Mrs Obama wrote how she wondered why so many women rejected "an exceptionally qualified female candidate and instead choose a misogynist as their President". "We laughed about how many hours were spent inside our heads, hoping a boy would ask us to dance, or stewing over a big test, just doing everything we could to avoid even the most minor embarrassments".
Her husband Prince Harry, 34, enjoys a close relationship with Mrs Obama, who has been a firm supporter of his Invictus Games.
"Trying not to fall is a major thing that I think about in public". They also said the two women had formed a strong bond "and planned to stay in contact". Alright, I'm back now. But her words have an element of truth that Sheryl Sandberg's optimistic ideology about "leaning in" to have it all doesn't take into account.
Obama, 54, was speaking to Good Housekeepingmagazine when the topic of the Duchess of Sussex came up. In a 2015 essay, New York Magazine contributing editor Lisa Miller explained how the labor force's unkind treatment of women affects not only older workers, but also young, ambitious professionals looking for role models.
She married into the royal family, which caused a media frenzy, and she also announced her pregnancy. "But after a while, I realized that I had every reason to be in those environments".