Blast from the past! Jennifer Aniston’s dating history includes a few familiar faces, some of whom she remained friendly with. 

From casual dates to marriages, the Friends alum remained amicable with some later in life. One of her most well-known relationships was with fellow actor Brad Pitt, who was a guest star on one episode of the iconic TV show. Although their marriage didn’t work out, the We’re the Millers actress and the Mr. & Mrs. Smith actor were able to create a friendship after they divorced in October 2005. 

Almost 15 years after splitting up, the former duo spent some time together at Jennifer’s Christmas party. 

“They’re obviously on friendly terms, and the more time that passes, the closer they seem to be getting,” a source informed In Touch in December 2019. “This show of solidarity, at a small gathering like this, is very special. It’s a very grown-up gesture on Jen’s part.

One month later, fans of the friendly exes freaked out after a sweet moment between Jen and Brad was captured on camera during the 2020 Screen Actors Guild Awards. During the awards ceremony, Brad won the award for Main Actor in a Supporting Role for Once Upon a Time…in Hollywood and Jennifer won Best Female Actor in a Drama Series for The Morning Show. While backstage, they briefly ran into each other and seemed to congratulate one another after embracing in a quick, friendly hug, even holding hands for a moment. 

“It all happened so fast, but at the same time, it felt like it was in slow motion,” a second source told In Touch in January 2020. “Brad and Jen happened to pass each other in the hall, right here in front of me. Everyone was a flutter, giddy with excitement.”

Aside from the Once Upon a Time…in Hollywood actor, Jennifer has also spoken highly of Paul Rudd, who was named People’s “Sexiest Man Alive” in 2021. The two had a romance when they were young and worked together in multiple projects, including The Object of My Affection, Wanderlust</…….