Michelle Obama isn’t here for timid dating. She’s here for experience, self-discovery, and not letting one bad date ruin the whole scene. On a recent episode of her IMO with Michelle Obama and Craig Robinson podcast, the 61-year-old former first lady got real with her brother about the modern dating world.
From the nerves that come with meeting someone new to the fine art of flirting, she shared the same advice she gives her daughters, 27-year-old Malia and 24-year-old Sasha.
The simple 3 words: “date a lot.”
© Scott Olson“I just try to get them to stay open to people,” Michelle said. “The thing that I did do was date a lot. And so when Barack showed up, I had experiences to compare him against. I knew a lot of (how) I didn’t like this. I didn’t like that.” The core of her philosophy is that dating isn’t about instantly finding the one, but about knowing yourself well enough to recognize the right match when it appears.
Why She’s All for Dating A Lot
For Michelle, dating widely wasn’t about playing games. Meeting different personalities, navigating awkward moments, and learning how you want to be treated all helped her figure out what she valued in a partner. “We try to sort of educate the girls by sharing our experiences,” she explained. “So my whole thing is date. Date a lot, and if you run into a bad date or have a bad experience, move on quickly.”
How Michelle met Barack
Michelle’s path to Barack Obama wasn’t a lightning bolt of fate. It started in a Chicago law firm where she was assigned to mentor a Harvard law student working as a summer intern. That intern was Barack.
© MANDEL NGANAt first, she wasn’t looking for romance. In fact, she admits she had zero intention of dating anyone at the time. And his glowing reputation among the firm’s partners made her assume he was, in her words, “kind of this nerdy guy.”
Then came the first phone call
“The voice was sexier than the image that I had about him,” she recalled on the podcast. “I was sort of like, ‘Ooh. I didn’t expect this.’” That spark would eventually grow into one of the most high-profile and enduring marriages in politics, but Michelle clearly credits her earlier dating life with preparing her to recognize Barack as the right choice.
© Penske Media via Getty ImagesSasha and Malia's love lives
Though the sisters keep their personal lives private, both have been linked to past relationships. Malia previously dated Rory Farquharson, and seen with Dawit Eklund, rapper Aminé, and photographer Achilleas Ambatzidis.
© GrosbyGroupWhile Sasha was at one point linked to writer-director Clifton Powell Jr., though the pair have since gone their separate ways. Michelle has even acknowledged in interviews that her daughters “have boyfriends and real lives,” underscoring that her advice about dating isn’t just theoretical.
A mom's advice that resonates today
Michelle’s “date a lot” mantra is more than just about finding a partner, it is prompt for self-discovery. In an era of dating apps and fast online connections, her wise words to her daughters is a reminder to stay open to different experiences feels timeless.
© Jacopo M. Raule- By staying open, you give yourself a better chance to meet different kinds of people.
- By comparing experiences, you sharpen your instincts.
- And by moving on quickly from bad fits, you protect your time and energy.
Encouraging Malia and Sasha to learn what they like (and what they don’t), the Obamas are passing along a grounded, practical approach to love that’s already stood the test of time in their own 30-year marriage.
