This article first appeared on

Kim Kardashian

Kim Kardashian is possibly the most successful socialite in human history, parlaying a sex tape scandal into a multi-million dollar fashion and reality TV empire. In the past decade, she was married to hip hop legend Kanye West (with whom she has several children) and even dated SNL breakout star Pete Davidson.

But even back in the day, the well-heeled Kim K had her sights on dating the stars. Recognise her prom date? It’s TJ Jackson, aka Michael Jackson’s nephew and star of short-lived Jacksons successor 3T! What can we say? She has a thing for musicians.

Jimmy Fallon

Jimmy Fallon has a reputation as a bit of a man-child, goofing around on The Tonight Show. But his slick showbiz schtick wasn’t developed overnight – he had to go through the same embarrassing prom pics as everyone else.

“The night before, my companion got a tan at the tanning salon. I did not. I looked like Powder. #awkwardpromstory,” Fallon once tweeted.

Bruno Mars

In many ways, it feels like Bruno Mars was born in the wrong era. Despite being one of the most successful pop stars in recent memory, a lot of his music seems to pay homage to bygone eras, particularly from decades such as the ’70s, ’80s, and ’90s.

The man behind hits such as “Uptown Funk” and “Just the Way You Are” enjoyed himself at his very own prom and didn’t stop himself from rocking some truly impressive Jheri curls!

Angelina Jolie

Years before she had a high-profile marriage to Hollywood hunk Brad Pitt, Angelina Jolie was a high school student at Moreno High School, where she was regarded as a “punk outsider.”

The daughter of screen star Jon Voight, though she had little contact with him during her childhood, Jolie was known for collecting knives, and few would have pegged her as the future beauty queen of Hollywood. Never judge a book by its cover!


Rihanna released her debut album at 17, had an international breakthrough at 19, and has since become one of the bestselling artists on the planet, as well as a leading fashion designer and political activist for her home country of Barbados. She was declared a national hero of the island nation in 2021, meaning her full title is in fact “the Right Excellent” Rihanna!

So why is it that her slacker prom date, with his curtain haircut, is acting like he’s the centre of attention?

Meghan Markle

At the age of 17, Meghan Markle was crowned the prom queen, long before she realized that she would one day become a member of the royal family of the United Kingdom. Her senior prom was held in the year 1998 at Immaculate Heart High School, which the now Duchess of Sussex attended in the city of Los Angeles.

As can be seen in the photo taken from the evening, Meghan Markle wore a tiara, a long ball gown, and silver jewelry, all of which gave her the appearance of a member of the royal family. It’s unlikely that her prom date had any idea who the person standing next to him at the time would turn out to be in the future.

Harry Styles

Before he became one of the most famous singers in the world with X Factor composite creation One Direction, and even more famous in his solo career, Harry Styles was a regular guy who worked at a fish and chip shop and went to school in Cheshire. Nowadays, Styles wouldn’t be seen dead having his picture taken in a car park, next to some double yellow lines.

As for his prom date… don’t worry, darling – you’ll find your beau someday!

Taylor Swift

Taylor Swift is the person who is best known for the fact that she has had a number of different guys in her life at the same time. Therefore, it should not come as a surprise that she took a date to the prom at the conclusion of her senior year of high school.

When it came time for Taylor to attend her prom, the young woman, who had not yet garnered a variety of honors and distinctions, went all out in terms of her appearance. In point of fact, Taylor Swift donned a white dress, while her boyfriend wore a spotless white suit and tie to the event.

Britney Spears

She was the southern belle that rose to fame after her hit debut single, “Hit Me Baby, One More Time,” but Britney Spears has never forgotten her roots. While she had already starred in The Mickey Mouse Club alongside many other famous faces, the pop princess made it to her Freshman formal dance, looking ever so glamorous.

She has since gone on to have many number one hits, sell millions of records, and even have her own residency in Las Vegas.

Brad Pitt

He has been voted as the most attractive man in the world in many media reports, and even as a high school student, Brad Pitt was sure to charm you with just his smile. Although sporting a different hairstyle to what most are used to for the actor, Brad Pitt was just another regular high school student back in the day, accompanying a lovely lady to their school prom.

In fact, this picture could be mistaken for a wedding photo with Pitt’s date dressed in a long, white, bridal-looking gown.