Jennifer Aniston & Justin Theroux

Before meeting Justin Theroux, Jennifer Aniston was tied to Brad Pitt. The former power couple got married after two years of dating in July 2000. The union seemed unbreakable, but in early 2005, the two announced the end of their marriage, which certainly saddened and shocked their fans. Later, she dated John Mayer from 2008 to 2009. A few years later, news flocked after Aniston was reportedly dating Theroux. By January 2012, the two purchased a breathtaking estate for over $20 million in Bel-Air with no mortgage loans involved. In August, the same year, they got engaged and eventually tied the knot in August 2015.

However, the two called it quits, which was only two years after the wedding. As a bankable actress, Aniston landed several projects like Mother’s Day and Storks, both released in 2016. These films probably helped her forget yet another failed marriage. Theroux, on the other hand, might have drunk a couple of bottles and then got back to the dating game again. He was in a relationship with another Emmy-award-winning actress, Emma Stone, in 2018.