Barack Obama's Reaction Says It All as Michelle Wears a One-of-a-Kind Skirt at Their Latest Outing – Photos
June 17, 2026

Sasha Obama stuns wearing a skimpy dress for her prom. He mother Michelle Obama and her sister beam with delight as they joined her in photos shared on Twitter.
Sasha Obama is a grown woman in photos from her prom. The 17-year-old let her hair down and showed some skin in a tight black dress.

Sasha Obama attending the 2016 State Dinner at the White House in honor of Prime Minister Justin Trudeau and First Lady Sophie Gregoire Trudeau of Canada. | Source: Getty Images
Sasha, who graduates from Sidwell High School next month, drew attention on Twitter when images of her and her date, Chris Milton were posted online. She looked stunning in a black slip dress with thin straps and a high slit. Her hair fell straight and sleek allowing her giant hoop earrings to stand out. Meanwhile, her date looked equally dashing in a traditional tux.
During a 2016 radio interview, he [Barack Obama] said he’s “pretty relaxed” when it comes to his daughters dating because of the example his wife set out for them.
Also spotted in the pictures were Sasha’s mother, Michelle Obama and her sister, Malia. Both were beaming in support of their youngest family member.
Barack Obama was noticeably missing from the occasion. He would have had a few words to say to Sasha’s date if he were there. He’s known to jokingly issue threats to the men who circle around his daughters in the past, most of which involving the Secret Service.
Sasha will be off to college in two years. She’s reportedly going to the University of Michigan after a gap year.
However, despite the fear he instills on these boys, the former president admits, he’s not worried. During a 2016 radio interview, he said he’s “pretty relaxed” when it comes to his daughters dating because of the example his wife set out for them.
“She’s such a great example of how she carries herself, her self-esteem, not depending on boys to validate how you look or not letting yourself be judged by anything other than your character and intelligence.”
Barack adds that he hopes kind of man he is to his wife would also enlighten his daughters about the kind of man they should seek.
“Hopefully, I’ve been a good example in terms of how I show respect to my wife,” he says.
Sasha will be off to college in two years. She’s reportedly going to the University of Michigan after a gap year. She shared the news on her Instagram in December, excited that she’ll be attending the Ann Arbor school with some friends. She even featured a photo of them standing in front of Michigan’s football stadium.
It seemed like only a minute ago when a seven-year-old Sasha was thrust into public life as her father became president. Now she’s off to prom and college. We’re sighing along with her parents.
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