Full Brad Pitt and Jennifer Aniston Relationship Timeline

Jennifer Aniston and Brad Pitt have gone from film’s hottest couple to husband and wife to nemeses to…great friends? It seems so: Pitt and Aniston have been seen more and more together in the years post-split. And now that Pitt and Aniston are both single once again, following Pitt’s ongoing divorce from Angelina Jolie and Aniston’s divorce from Justin Theroux, debating whether or not they will (or should) reunite has become a national pastime.

After a certain SAG awards ceremony, fans went into overdrive. You know, the one where the exes were spotted together publicly for the first time in a while and appeared to be delighted to see each other? Since then, fans have been convinced it’s just a matter of time until the two get together again, even though the exes insist they’re just good friends. They’ve have been anxiously awaiting any and all updates, included a very special Zoom scene the two did together (if you don’t know what we’re talking about, just wait ’til you see it). In honor of The Great Debate, let’s take a look back at Brad and Jen’s love story, spanning over a quarter of a century, and the latest developments.

Table of Contents

1994

the mexican premiere

(Image credit: Kevin Winter / Getty Images)

The two cross paths for the first time, and Hollywood is forever changed. In an interview with Rolling Stone, Aniston says they first met back in 1994 since their managers were friends. “[Pitt] was just this sweet guy from Missouri, you know? A normal guy,” she said. 

1998

leather jacket, jacket, leather, textile, event, outerwear, fashion, jeans, long hair, top,

(Image credit: Getty Images)

Pitt and Aniston go on their first date after being set up by their agents—a true Hollywood romance, right? They try to keep things quiet for as long as they can, but this proves difficult since Pitt is one of the biggest movie stars in the world and Aniston is America’s sweetheart. (Also, big ups to their beauty lewks in this photo.)

September 12, 1999

fashion, eyewear, event, fashion design, formal wear, dress, suit, little black dress, glasses, fashion accessory,

(Image credit: Getty Images)

Pitt and Aniston make their public debut as a couple on the red carpet for the Emmy Awards in 1999—forever immortalizing Brad’s sunglasses.

November 21, 1999

performance, entertainment, performing arts, musician, event, concert, social group, music, music artist, public event,

(Image credit: Getty Images)

Just a few months after that initial debut, Pitt and Aniston crash the stage of a Sting concert (ha ha ha ha) in New York City and flaunt their engagement. In their defense, there was no Instagram back then.

July 29, 2000

aerial photography, landscape, photography, architecture, house, world, screenshot, building, village, games,

(Image credit: Getty Images)

Pitt and Aniston tie the knot in a lavish Malibu wedding, which is naturally hounded by paparazzi—thus the aerial shots. Look at all those tents! The phrase “media circus” couldn’t be more apt.

July 29, 2000

fireworks, new years day, night, midnight, sky, holiday, event, diwali, new year's eve, darkness,

(Image credit: Getty Images)

There are literally fireworks the night of the wedding. It was that lavish.

September 10, 2000

Brad and Jen

(Image credit: Getty Images)

Pitt and Aniston make another appearance at the Emmy Awards, this time as newlyweds (and looking classy AF, we might add).

September 2001

event, fashion, smile, fun, blond, formal wear, suit, nightclub, party,

(Image credit: Getty Images)

Aniston talks about Pitt in an interview with Rolling Stone. She admits that her friends worried he would be a “conceited f*ck” at first, but immediately came around because he’s actually just the best person. She also talks marriage and being in it for the long haul.

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