A Look Back on Brad Pitt, Jennifer Aniston's First Date

Fifteen years into Brad Pitt and Jennifer Aniston calling it quits, their relationship continues to pique interest from fans across the globe. The pair's romance was the talk of Hollywood in the late 1990s and early 2000s. Pitt publicly then moved on with Angelina Jolie shortly after.

At the 2020 Screen Actors Guild Awards, the amicable exes were photographed together for the first time in years.

Pitt, 56, and Aniston, 50, who were married for 5 years between 2000 and 2005, had a friendly moment at the 2020 SAG Awards. They were shot embracing and briefly holding hands, looking pleased to see each other.

Pitt and Aniston are now reportedly rekindling their friendship.

Back in 1998, the respective agents of the former couple played matchmaker and set them up for a date in true Hollywood fashion.

Before their meet-up, Aniston recalled, "(Pitt) was just this sweet guy from Missouri, you know? A normal guy."

The "Fight Club" actor and "Friends" actress and had met shortly after Pitt had called off his two-year-engagement with Gwyneth Paltrow. Aniston also called off her engagement with actor Tate Donovan whom she had been dating since 1995.

"It was weird...That was a really easy evening," according to Aniston in a 2004 interview. "That was really fun."

Both tried to keep their romance under wraps but at that point, Pitt was one of Hollywood's biggest stars and Aniston was America's sweetheart. At the time, it was a world before the advent of channels and streaming platforms, about 30 million people were watching Aniston's sitcom every week.

The former flames made their relationship red carpet-official at their first public appearance at the Emmy Awards in Los Angeles in 1999. "Friends" was nominated for outstanding comedy series but lost out to "Ally McBeal." With Pitt's tiny sunglasses and Aniston's unique half-messy hair, the Southern Californian style was one of the most recognizable moments for the pair to date.

Also Read: Brad Pitt, Jennifer Aniston About to Announce Relationship in Tell-Tale Interview?

A couple of months later, Pitt and Aniston interrupted a Sting gig in New York City to declare to the world that they were engaged with Aniston flaunting her ring.

In July 2000, the former couple tied the knot in a lavish Malibu wedding with helicopters circling the venue in attempts to capture any moment they could. Paparazzi hounded the celebration, photographing aerial shots. The event included 200 guests, 50,000 flowers, 4 bands, a gospel choir, and fireworks.

Aniston reminisced in an interview, "I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way."

Preceding their divorce, The "Fight Club" star co-starred with Angelina Jolie on the set of "Mr. & Mrs. Smith" and the rest was history for Pitt and Aniston.

In mid-December last year, Pitt was among 50 friends who were present at a holiday party at Aniston's Bel-Air home. According to an eyewitness, he was the second to the last guest to leave.

Fans are still hopeful that the pair will reignite their romance.

The "Office Christmas Party" actress spoke fondly of both her former spouses in a story published in December 2018, "My marriages, they've been very successful, in (my) personal opinion. And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness didn't exist within that arrangement anymore."