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Aniston didn't start dating her ex-husband Justin Theroux immediately after splitting from Brad Pitt. In between the two, she was linked to a handful of guys, including Mayer. The on-and-off couple got together in April 2008 and looked smitten at the 2009 Vanity Fair Oscar party together but broke up for good shortly thereafter.
Following their final split, he had nothing but kind things to say about Aniston in his infamous 2010 Playboy interview. "We just have a regard for each other's feelings that is pretty intense," he told them, before denying that Aniston is the inspiration for his song "Heartbreak Warfare." "I feel bad because people think 'Heartbreak Warfare' is about her," he said. "I want to go on record saying it's not. That woman would never use heartbreak warfare. That woman was the most communicative, sweetest, kindest person."