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Jennifer Aniston & Brad Pitt’s Cutest Couple Moments Over The Years

By:
Medina Lynn
March 26, 2018 9:26PM EDT

Brad Pitt and Jennifer Aniston were one of Hollywood’s ‘it’ couples when they were together. Take a look at photos of Brad and Jen over the years.

1 of 21

Jennifer Aniston & Brad Pitt

Jennifer Aniston & Brad Pitt
REX/Shutterstock

Even though it’s been more than 15 years since Brad Pitt and Jennifer Aniston ended their marriage, they remain one of Hollywood’s most buzzed-about duos. Brad and Jen first met in 1998, and were married in a super private ceremony in Malibu in 2000. However, in Jan. 2005, they announced their decision to separate, and he filed for divorce later that year. The separation came amidst reports that Brad had gotten close with his ‘Mr & Mrs. Smith’ co-star, Angelina Jolie. The love triangle became the subject of media scrutiny, and has remained a hot tabloid story ever since. Brad and Angie went on to get married, but split in 2016. Throughout the years, Brad and Jen have remained friendly, and they reunited in person at her 50th birthday party in 2019, as well as at the SAG Awards in 2020. Check out all their cutest moments over the years here!

March 26, 2018, 9:17PM
2 of 21

Brad Pitt & Jennifer Aniston At SAG Awards

Brad Pitt & Jennifer Aniston At SAG Awards
The Grosby Group / BACKGRID

Brad Pitt and Jennifer Aniston say a quick hello to each other while backstage at the 2020 SAG Awards. It was thier first public reunion since splitting in 2005.

January 23, 2020, 12:58PM
3 of 21

Brad Pitt & Jennifer Aniston At Award Show

Brad Pitt & Jennifer Aniston At Award Show
Berliner Studio/BEI/Shutterstock

Brad Pitt and Jennifer Aniston cozy up at a table during an award show. He couldn’t keep his eyes off of his then-wife at the event.

January 23, 2020, 12:58PM
4 of 21

Jennifer Aniston & Brad Pitt At An Event

Jennifer Aniston & Brad Pitt At An Event
REX/Shutterstock

Jennifer Aniston & Brad Pitt pose for photos together at an event while they were still an item.  They both sported blonde locks as they cozied up for a pic.

March 26, 2018, 9:17PM
5 of 21

Jennifer Aniston & Brad Pitt On The red Carpet

Jennifer Aniston & Brad Pitt On The red Carpet
REX/Shutterstock

Jennifer Aniston & Brad Pitt hold hands as they arrive to a glamorous red carpet event, with Jen looking absolutely stunning in a red dress. The two were surrounded by cameras as they made their way down the carpet.

 

March 26, 2018, 9:17PM

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6 of 21

Brad Pitt Holding Jennifer Aniston

Brad Pitt Holding Jennifer Aniston
REX/Shutterstock

Jennifer Aniston & Brad Pitt look so happy while posing with his hands on her waist at an event. She wore a plunging black dress with an open back, while he was dapper in a suit.

 

March 26, 2018, 9:17PM
7 of 21

Jennifer Aniston & Brad Pitt Holding Hands

Jennifer Aniston & Brad Pitt Holding Hands
REX/Shutterstock

Jennifer Aniston & Brad Pitt hold hands while heading out on a date night back when they were together. Both stars wore all black for their night on the town.

 

March 26, 2018, 9:17PM
8 of 21

Jennifer Aniston & Brad Pitt Hold Hands At An Event

Jennifer Aniston & Brad Pitt Hold Hands At An Event
REX/Shutterstock

Jennifer Aniston & Brad Pitt keep close while wearing matching tan outfits to an event. They held hands as they were surrounded by paparazzi.

March 26, 2018, 9:17PM
9 of 21

Jennifer Aniston & Brad Pitt Laughing

Jennifer Aniston & Brad Pitt Laughing
REX/Shutterstock

Jennifer Aniston & Brad Pitt can’t contain their smiles as they pose for photos together on the red carpet. Jen wore a maroon outfit, with an embellished bodice and solid skirt.

 

March 26, 2018, 9:17PM
10 of 21

Jennifer Aniston & Brad Pitt Hugging

Jennifer Aniston & Brad Pitt Hugging
REX/Shutterstock

Jennifer Aniston shows off her abs in a crop top while cozying up to Brad Pitt. They wrapped their arms around each other as they posed for photos.

 

March 26, 2018, 9:17PM
11 of 21

Jennifer Aniston & Brad Pitt Taking Red Carpet Pics

Jennifer Aniston & Brad Pitt Taking Red Carpet Pics
REX/Shutterstock

Jennifer Aniston & Brad Pitt wrap their arms around each other while taking red carpet photos. Jen looked absolutely stunning in her plunging black dress at the event.

 

March 26, 2018, 9:17PM
12 of 21

Jennifer Aniston & Brad Pitt Looking At Each Other

Jennifer Aniston & Brad Pitt Looking At Each Other
REX/Shutterstock

Jennifer Aniston & Brad Pitt gaze into each other’s eyes while taking pictures at the Golden Globes. They wore matching black suits and looked totally fierce at the award show.

 

March 26, 2018, 9:17PM
13 of 21

Jennifer Aniston & Brad Pitt Taking Photos Together

Jennifer Aniston & Brad Pitt Taking Photos Together
REX/Shutterstock

Jennifer Aniston & Brad Pitt are glowing while taking photos on the red carpet together. Jen showed off her abs in a crop top and low-slung white pants.

March 26, 2018, 9:17PM
14 of 21

Jennifer Aniston & Brad Pitt Smiling

Jennifer Aniston & Brad Pitt Smiling
REX/Shutterstock

Jennifer Aniston & Brad Pitt are all smiles while looking at one another on the red carpet. Jen was stunning in her white, halter style dress, which featured silver embellishments.

 

March 26, 2018, 9:17PM
15 of 21

Jennifer Aniston & Brad Pitt Posing On Red Carpet

Jennifer Aniston & Brad Pitt Posing On Red Carpet
REX/Shutterstock

Jennifer Aniston & Brad Pitt keep it cool in their dress and tux during a red carpet appearance. Jen was all smiles, while Brad kept it cool in his sunglasses.

 

March 26, 2018, 9:17PM
16 of 21

Jennifer Aniston & Brad Pitt At ‘Spy Game’ Premiere

Jennifer Aniston & Brad Pitt At ‘Spy Game’ Premiere
Eric Charbonneau/BEI/REX/Shutterstock

Brad Pitt and Jennifer Aniston attend the premiere of ‘Spy Game’ as a couple. They wrapped their arms around each other to pose for photos at the event.

February 15, 2019, 10:35AM
17 of 21

Jennifer Aniston & Brad Pitt At ‘The Mexican’ Premiere

Jennifer Aniston & Brad Pitt At ‘The Mexican’ Premiere
Bei/REX/Shutterstock

Jennifer Aniston and Brad Pitt cozy up for photos at ‘The Mexican’ premiere in 2001. Brad held Jen close as they took pictures on the red carpet.

February 15, 2019, 10:35AM
18 of 21

Jennifer Aniston & Brad Pitt At ‘Erin Brockovich’ Premiere

Jennifer Aniston & Brad Pitt At ‘Erin Brockovich’ Premiere
Chris Pizzello/AP/REX/Shutterstock

Brad Pitt and Jennifer Aniston arrive at the premiere of the film “Erin Brockovich” in the Westwood section of Los Angeles. They linked arms as they smiled and walked inside.

February 15, 2019, 10:35AM
19 of 21

Jennifer Aniston & Brad Pitt At Emmy Awads

Jennifer Aniston & Brad Pitt At Emmy Awads
Slocomb/Mediapunch/REX/Shutterstock

Jennifer Aniston and Brad Pitt couple up at the Emmy Awards in 2002. They both rocked pretty wild hairstyles as they made their way down the carpet.

February 15, 2019, 10:35AM
20 of 21

Jennifer Aniston & Brad Pitt At Independent Spirit Awards

Jennifer Aniston & Brad Pitt At Independent Spirit Awards
Peter Brooker/REX/Shutterstock

Brad Pitt and Jennifer Aniston laugh it up at the Independent Spirit Awards in 2003. Brad wore sunglasses, while Jen kept it casual in a simple black outfit.

February 15, 2019, 10:35AM
21 of 21

Jennifer Aniston & Brad Pitt At 2002 Golden Globes

Jennifer Aniston & Brad Pitt At 2002 Golden Globes
Matt Baron/BEI/REX/Shutterstock

Jennifer Aniston and Brad Pitt look so in love while posing at the Golden Globes in 2002. They gazed into each other’s eyes while taking photos on the carpet.

February 15, 2019, 10:35AM
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