Did Jennifer Aniston Ever Date Jason Sudeikis? Why Romance Reportedly Isn't On The Table

It has been a long-standing rumor that Jennifer Aniston and Jason Sudeikis were once more than friends. The pair have starred in several films together, even proving their on-screen chemistry in the 2013 comedy "We're the Millers," but Sudeikis and Aniston's relationship has seemingly never gone romantic. That's not to say Sudeikis hasn't tried to form a relationship with the "Friends" alum. The Los Angeles Times reported that the DVD extras for Aniston and Sudeikis' 2010 movie "The Bounty Hunter" included an interview where the "SNL" great admitted his 15-year-long crush on his co-star. Even when he later asserted to GQ that he was joking, an insider reportedly revealed the truth. 

A source told Star Magazine in 2022 that Sudeikis once asked mutual friends to fix him up with Aniston, attempting to date her (via OK!). Aniston reportedly didn't react the way her "Horrible Bosses" co-star would have wanted; the source said, "Jen kind of shudders when people suggest they date. Jason's not her type at all." She apparently only sees him as a friend, with the source saying, "Their chemistry is more brother-sister than anything else." Considering a source told Us Weekly that "more than anything, she's after chemistry," it sounds like Sudeikis doesn't have a shot — though some people are hoping he does. 

Both Jennifer Aniston and Jason Sudeikis have been in a few high-profile relationships. Aniston was famously married to Brad Pitt from 2000 to 2005 (before it was rumored he cheated on her with Angelina Jolie) and Justin Theroux from 2015 to 2018. Sudeikis was married to screenwriter and producer Kay Cannon before his headline-making engagement and breakup with actor Olivia Wilde — they share two children. When it was reported that Wilde had quickly moved on with pop star Harry Styles, Aniston was reportedly there for him (in true "Friends" fashion). "She's been an absolute rock for Jason throughout this nightmare. They talk and text every day," a source told Heat Magazine at the time (via Mirror). Fans have noticed their close bond and haven't been quiet about their hope for a future romance.

Social media matchmakers have taken to X, formerly Twitter, to express their desire to see Aniston and Sudeikis together. "I was watching #MothersDay with Jennifer Aniston and Jason Sudeikis and I was thinking, they would make a real nice couple. So, yes I am shipping Jenn and Jason," one user said. "I ship jennifer aniston and jason sudeikis," someone else wrote. Another commented: "Honestly though how is it possible for jason sudeikis and jennifer aniston to be that hot together i dont get it." We want "Sudeniston" to happen as much as a "We're The Millers 2."