Rudd played Aniston's gay best friend in the 1998 rom-com "The Object of My Affection," and the two were rumoured to have struck up a brief romance, as per Page Six. The two stayed friends and even worked together a few more times; Rudd starred as Lisa Kudrow's onscreen husband, Mike, on "Friends," and he and Aniston starred as a couple in 2012's "Wanderlust." (Fun fact: Aniston fell in love with Justin Theroux on the film's set in 2010.)
While promoting the film, the duo were asked in an interview with GQ if it was "weird to kiss" on screen, having been close for such a long time. Aniston remarked, "Nah. I've kissed him for years," while Rudd quipped, "We've made out for decades."