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Home » All Listicles » All Grown Up! Malia & Sasha Obama Turn Heads With RARE Sighting At Album Listening Party (PHOTO)
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All Grown Up! Malia & Sasha Obama Turn Heads With RARE Sighting At Album Listening Party (PHOTO)

By Cassandra - 2025/04/30
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Malia Sasha Obamas Rare Sighting Destin Conrad Album Listening Party PHOTO
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Malia and Sasha Obama recently popped out for some artistic fun, and a rare photo of them has social media going wild! The sisters became household names at ages 10 and 8 when Barack Obama became president. Now, at 26 and 23, they’re doing their own thing, managing to stay out of the spotlight most of the time! In the circulating picture, Malia and Sasha posed with Destin Conrad at the listening party for his debut album.

RELATED: Message From The Palace! Momma Dee Reacts After Michelle Obama Reveals She’s A Fan Of ‘Love & Hip Hop’ (WATCH)

Malia & Sasha Obama Slay Like THIS In Newly Surfaced Photo

As said, the Obama sisters stepped out to support Destin’s project, ‘Love On Digital,’ which dropped on streaming platforms on April 25. It’s unclear when exactly the listening party took place, but it was likely before the album release. However, the rare photo of Malia and Sasha seemingly appeared on Instagram for the first time on Tuesday (April 29). Photographer Ryder shared the content in an Instagram carousel. Ryder also photographed other celebs, like Kehlani, at the event for Destin Conrad.

In the circulated photo of the sisters, Malia and Sasha stood on opposite ends of Destin with him in the middle. On the left, Malia Obama rocked ginger-colored, loose waves flowing down her chest. She also wore a deep brown jacket while cheesing for the camera. In contrast, Sasha Obama had on a cropped white tee, with black undergarments, and low-rise jeans, meaning her midsection was out. Her hair was black, and she slightly smiled for the moment.

What Else Has Been Up With The Obama Sisters?

It’s been over a month since Malia and Sasha Obama were last spotted publicly. At the time, the sisters were out with their dad, Barack, for dinner. Photos show them leaving the restaurant in Los Angeles. Malia appeared to be wearing the same deep brown jacket as her Destin Conrad photo. She paired the look with a jean skirt and tall boots. Meanwhile, Sasha rocked a leather trench coat, dark baggy pants, and a black shirt.

According to HOLA!, the Obama sisters have been out and about in L.A., particularly at exclusive events, running errands, or grabbing something to eat. Malia is in Los Angeles pursuing an entertainment career after taking a gap year after high school, then attending and graduating from Harvard in 2021. She’s rocked on actual productions, too, per PEOPLE. That includes internships with the Weinstein Company and on the show ‘Girls.’ She’s also worked as a production assistant for the series, ‘Extant,’ and a writer on Donald Glover’s ‘Swarm.’ In 2024, she debuted her first short film, ‘The Heart’, at the Sundance Film Festival under the name Malia Ann. Her 27th birthday is around the corner on July 4.

In a few weeks, on June 10, Sasha will also celebrate her 24th birthday. After graduating from high school in 2019, she enrolled at the University of Michigan but later took online classes due to COVID-19. Both Obama girls lived at home during the pandemic before relocating to L.A. to live together. Sasha completed her undergraduate degree in sociology at the University of Southern California in May 2023. It’s unclear what she currently does for work.

#1

Social Media Sounds OFF About Rare Sisters' Photo

As the photo of Malia and Sasha at Destin’s party made its rounds, social media weighed in on the sisters’ growth! In The Shade Room’s comment section, the roommates were gagged at the image and went off with reactions!

“Man I almost said “that ain’t Sasha!!!” Baby, yes it is 😂😂😂 PERIOD,” @angailthegreat wrote.

“I love when sisters SISTER the way they sister! 😍,” @themorangirl said.

“I can’t explain it but it gives Beyoncé and solange🔥😍,” @hey_mickie commented.

“Them being this grown makes me feel old 😂😂😂😂,” @mykel_hilliard added.

@_tokyo_slimm_ wrote, “Big Sasha not the lil one😍😍😍😍😍 both look gorgeous 🔥🔥🔥”

“Sasha been eating her rice and cabbage! Okay sis! Almost didn’t recognize her,” @spunky_brewstah added.

Meanwhile, @bq.garrett wrote, “Maliaaaaa do you see her!!!! Sashaaa girl wowww ! Careless and free black girls 🥰” 

@sirjoeexclusive commented, “I thought the comment was a joke till I zoomed in…. Okkk Lil Obamas❤️❤️ They grown now haha.”

@ayshadaysh complimented them both, writing, “Two different mealssss, but they both eat! 😍”

#2

Michelle Obama Recently Spoke About Her Daughters

Like her daughters, Michelle Obama has been carving her own path since leaving the White House. These days, the former First Lady has allowed a more intimate look at her life behind closed doors, thanks to her new co-hosted podcast. In recent episodes, she’s spoken on a lil’ bit of everything, from why she didn’t attend Trump’s inauguration to her love for reality TV, like ‘Love & Hip Hop.’

Michelle has also been keeping it 100 on interviews with other outlets, like when she shut down divorce rumors on the podcast ‘Work In Progress.’ Most recently, she opened up about the challenges of keeping Malia and Sasha out of the tabloids once they entered their teenage years in the White House. According to E!, she explained to Kelly Ripa on ‘Let’s Talk Off Camera’ that the period was “a lot of work,” especially giving them a sense of normalcy.

“They had to drive and they had to go to prom and they were on teams and they traveled to other schools and they had to do college searches, and they went to parties and they had drinks, and they tried out smoking and they did all the things,” Michelle said. Adding, “and every weekend was a nightmare, because we had to work to make sure that them being regular teenagers didn’t wind up on Page Six.”

These days, though, she’s letting her daughters take the wheel in their own lives, and handle the responsibility of the “Obama tax,” which is being ultra famous forever. “You’ll have it the rest of your life, but you also have a lot of benefits,” Michelle said.

RELATED: Let ‘Em Know! Michelle Obama Speaks On Skipping Donald Trump’s Second Inauguration & Receiving Backlash (LISTEN)

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Cassandra Santiago

Cassandra Santiago

Cassandra Santiago is a multimedia journalist, editor, and editorial strategist with over a decade of experience shaping conversations across arts, entertainment, culture, and global news. A graduate of the University of Iowa, she has built a cross-platform career spanning newspapers, magazines, radio, and digital media. She joined The Shade Room five years ago and currently serves as a Senior Editor, where she leads editorial direction, oversees exclusive coverage, and trains and edits a team of writers. Cassandra has played a key role in developing high-impact content and editorial strategies for an audience of more than 30 million, contributing to platform growth, engagement, and monetization across multiple channels. In addition to her leadership role, she remains a daily contributor, with her articles generating more than 41 million views since 2023. Beyond The Shade Room, Cassandra offers freelance social media strategy services, speaks on the influence and impact of Black media at public panels, and owns Did It For You, an event design company in the DC, Maryland, and Virginia area. She is Poynter Institute–certified and was named to the DMV’s 35 Under 35 list in 2024.

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