Sasha Obama strikes up surprising friendship with rapper Megan Thee Stallion

By Daily Mail (U.S.) | Created at 2026-08-19 03:15:57 | Updated at 2026-08-20 03:45:10 1 day ago

It looks like Sasha Obama may have a new best friend: rapper Megan Thee Stallion.

According to Page Six, the former First Daughter, 25, was recently spotted at the Sand Bar & Grille on Martha’s Vineyard hanging out with Megan, 31.

A source told the outlet that the two were 'looking like besties' during the outing.

The sighting comes just days after Sasha's mom, former First Lady Michelle Obama, hosted the rapper on an episode of her podcast, IMO, and said that Megan reminded her of Sasha. 

During the episode, Michelle and her brother Craig Robinson, who acts as her co-host, both admitted that Megan felt like someone who would 'be in their family.'

'You remind me of Sasha, my youngest,' Michelle told Megan.

'You and Sasha have similar sass levels,' she added.

Megan then recalled the time she had hung out with Sasha after her Saturday Night Live performance. 

It looks like Sasha Obama (seen in June), 25, may have a new best friend: rapper Megan Thee Stallion 

According to Page Six, the former First Daughter was recently spotted at the Sand Bar & Grille on Martha’s Vineyard hanging out with Megan (pictured in June)

'I made my security be all around [her]. I was like, "Hold on, y'all, we got the president daughter in here,"' Megan joked.

'She is just all up in it and your energy, it's just so familiar,' Michelle told Megan. 'It's like family.'

This summer, the Obama family has been spotted multiple times on Martha's Vineyard, where they own an $11.75 million mansion.

In July, the former First Lady was seen at Norman's restaurant in Oak Bluffs for an event hosted by The Vineyard Icon Foundation, where she danced it up with the crowd. 

Michelle looked younger than ever as she showed off her dance moves, wearing a strappy white tank top which had an open-style back and Bermuda-style jean shorts.

She completed her youthful look with a pair of oversized, aviator-style sunglasses.

Michelle appeared to be in great spirits and was seen dancing and embracing an attendee in footage shared via Instagram by The Vineyard Icon Foundation.

Another clip showed Michelle grooving to the song Wobble along with members of the crowd.

The sighting comes just days after Sasha's mom, former First Lady Michelle Obama , hosted the rapper on an episode of her podcast, IMO, and said that Megan (seen in June) reminded her of Sasha 

This summer, the Obama family has been spotted multiple times on Martha's Vineyard, where they own an $11.75 million mansion. They're seen at an event in Chicago in June

This summer, Michelle also revealed that her two daughters, Sasha and eldest Malia, 28, had gotten her hooked on the reality show Love Island.

'That's mother-daughter time, you know. And they're behind, they got me hooked,' Michelle revealed during a chat with actress Quinta Brunson on her podcast in June.

'And I was like, "Have you started the next season?" And they were like, "No! We're busy!" [I said], "You need to get some more free time!"'

In the years since leaving The White House, Malia graduated from Harvard and pursued a career in Hollywood.

Her directorial debut, The Heart, was released in 2024.

Sasha, meanwhile, graduated from the University of Southern California in 2023.

Michelle shares daughters Sasha and Malia with her husband Barack Obama, the former president of the United States.

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