While the 45-year-old actor has been happily married to wife Viveca, the mother of his three sons, for 11 years, he admitted he was a slow starter when it came to the opposite sex.
He told USAToday: "In my mind's eye, it seemed like the way it was supposed to happen."
However, Will's mother was convinced he had slept with a girl in High School who she disapproved of.
He explained: “She said, 'I'm telling you now, if you slept with this girl, you'd better slap a condom on that pecker of yours.'"
Will also revealed he worries his fans are underwhelmed when they meet him.
While the 'Anchorman' star is known for playing zany characters onscreen, he admits his normalcy offscreen often puzzles his fans.
He explained: "Meeting fans, I'll be like, 'Oh, hey, how are you?' And, literally, they're like, 'What are you going to do? Do something! Are you sure that's him? He's not doing anything!' Yes, I fear they're horribly underwhelmed."
Yet, Will does have one strange quirk.
He said: "I rotate my clothes so everything is equally worn. I rotate my tennis shoes as well, so sometimes that can mean black shirt with orange shorts and red shoes, which I don't give a s**t about, but my wife will be like, 'Really?'"