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