In 2008, David had romantic love affairs with Playboy Playmate Jillian Grace. They also welcomed a daughter, Harper that year. However, this love life didn't last that long. He has never been married and he has not been lucky spouse till date.
After his parents got divorced, David began living with his mother. He joined Saguaro High School and then he attended Arizona State University. He finally earned his bachelor's degree in business from there in 1986. While he was in this University, he also performed standup and that was at the university's comedy show, Farce Side Comedy Hour. In 1990, he joined Saturday Night Live as a writer and also as a cast of that show. As an actor, he is mainly known for his role in the movies like Grown Ups, Grown Ups 2, Joe Dirt 2: Beautiful Loser and many more. His net worth is said to be around $40 million.