Sasha Obama, 25, and rapper Megan Thee Stallion, 31, have reportedly developed a friendship, recently being seen together at the Sand Bar & Grille on Martha's Vineyard. A source described the pair as "looking like besties" during their outing, according to Page Six.
This sighting follows a recent appearance by Megan Thee Stallion on former First Lady Michelle Obama's podcast, ";" where Michelle Obama remarked that the rapper reminded her of her younger daughter. During the podcast episode, Michelle and her co-host brother, Craig Robinson, noted that Megan Thee Stallion had an energy that felt familiar, akin to someone who could be part of their family. "You remind me of Sasha, my youngest," Michelle Obama told the artist, adding, "You and Sasha have similar sass levels."
Megan Thee Stallion recalled a previous encounter with Sasha Obama after a Saturday Night Live performance. "I made my security be all around [her]. I was like, 'Hold on, y'all, we got the president daughter in here,'" the rapper recounted, joking about the situation. Michelle Obama responded, "She is just all up in it and your energy, it's just so familiar. It's like family."
The Obama family has been a frequent presence on Martha's Vineyard this summer, where they own a mansion valued at $11.75 million. In July, Michelle Obama was seen at an event hosted by The Vineyard Icon Foundation, where she danced with attendees. Videos shared on Instagram showed her in a white tank top and jean shorts, dancing to music.
Earlier this summer, Michelle Obama also shared that her daughters, Sasha and Malia, had introduced her to the reality television show "Love Island." She described it as "mother-daughter time."
Malia Obama, 28, graduated from Harvard and has since pursued a career in Hollywood, with her directorial debut, "The Heart," released in 2024. Sasha Obama graduated from the University of Southern California in 2023. Michelle and former President Barack Obama are parents to both Malia and Sasha.