Sometimes it's hard to remember that Jennifer Aniston didn't start dating current husband Justin Theroux after splitting from Brad Pitt. In between the two, she was linked to a handful of guys, including John. 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 Jen in his infamous Playboy interview. "We just have a regard for each other’s feelings that is pretty intense," he told them, before revealing Jen is "the most communicative, sweetest, kindest person."