Before announcing on Thursday that they were calling it quits after two and a half years of marriage, the former lovebirds took a vacation to Cabo San Lucas, Mexico, over the holidays.
Aniston, 49, and Theroux, 46, were last photographed together on New Year's Day, soaking up the sun with friends during their getaway. The former Friends star rocked a bright red string bikini, while Theroux went shirtless, sporting blue shorts and a baseball cap. While there wasn't any tremendous PDA caught on camera, the two did seem to stay close to each other throughout the day.
Interestingly enough, when Aniston and Brad Pitt called off their five-year marriage back in 2005, the announcement also came shortly after the two seemingly took a farewell trip to the Caribbean. At the time, they were spotted holding hands on the beach.
Aniston and Theroux's joint statement announcing their separation confirmed they decision to part ways happened around their Cabo trip, stating, "This decision was mutual and lovingly made at the end of last year."
Their vacation came just a few months after they were last spotted together in New York City. Back in October, The Leftovers star wore a dapper fall look, consisting of a blue turtleneck sweater paired with dark-wash skinny jeans, yellow suede boots and a beanie, while Aniston, chic in distressed jeans, a blue top and brown fedora, followed closely behind him.
A source told ET on Thursday that their split was actually a long time coming, and that one of their major arguments over the years was in regard to where they should live. Theroux loves New York, while Aniston is more of a Cali girl.
"[Justin] much prefers being [in New York] and that's been a major issue for them for a long time," the source explained. "Justin has a very diverse friend group, and he likes that they're not all 'in the industry.' He's friends with people in the restaurant world, writers, comedians, artists, tattoo artists. It's an eclectic group and he doesn't have that type of network in L.A."
"Justin can hop on his [motorcycle], walk in the neighborhood, hang at a bar and all that without being bothered, but for Jen, the paparazzi are all over her," the source added, telling ET that Aniston and Theroux didn't share the same love for the Big Apple. "She just never really could get settled in, she wasn't happy [in New York]."
Three months prior to their last joint appearance in the Big Apple, Aniston and Theroux attended a ceremony for their close pal Jason Bateman, who was being honored with a star on the Hollywood Walk of Fame. The two were all smiles, cuddled up close to each other for the July event in Los Angeles.
As for an appearance together this month? That came in the new issue of Architectural Digest, which highlights the former couple's Bel-Air home. Although they're not technically pictured together, they were photographed separately for the same feature in their shared home.
Once the breakup announcement was made, many speculated that the magazine piece was a possible sign that the two were planning to sell the property. However, a source told ET on Thursday that the mansion is not for sale.
"The home is not currently for sale or a pocket listing, or off-market listing either, although that could change," the source explained.
Aniston was spotted out and about in Los Angeles on Thursday, just a few hours after the announcement was made. She was photographed arriving to a film studio, seemingly trying to keep a low profile. Hear more (and see the pics!) in the video below.