16. John Mulaney & Olivia Munn

John Mulaney is a prominent comedian in Hollywood. Not only does he spend his investments as an actor, but he also displays his comedic crafts as a writer and producer. Most of us know him from his stint at the world-famous long-running sketch show Saturday Night Live, but his achievements stretch to being a stand-up comedian. He has multiple stand-up specials to his name which include his Emmy Award-winning Kid Gorgeous in 2018.

In 2014, Mulaney married Annamarie Tendler. They were together for over six years but would eventually call it quits. Although the comedian kept the details of their separation private, it wouldn’t take long before the gossip around the industry would spread of him dating someone new. Months after his separation, he was seen dating Olivia Munn. According to PEOPLE, the couple has known each other for quite some time now and have been friends. They first met at a church in Los Angeles.