David was born on Long Island, New York, to a family with two sisters, Betsy and Helen, who would later become a gifted actor herself. When David was four, his family relocated to Illinois, settling in the suburbs of Chicago, where he spent his formative years.
As a youth, David worked summers to save for college, which unfortunately lasted only five weeks before he was expelled. During this time, he met Ken Stien, a local horseman who became a mentor and lifelong friend. David's teenage years were marked by trouble, including run-ins with the local police, and it took him several years to get back on track.
David's interest in acting began at age 12, when he landed a part in a community theater production of Kurt Vonnegut's "Happy Birthday, Wanda June." The play was a risqué choice for a small town, and David received his first and only positive review from the local critic. He went on to perform in a few more local plays and musicals before high school, where he struggled academically and developed a reputation as a class clown.
After high school, David attended the University of Iowa, where he studied social work. However, he soon dropped out and moved back to Naperville, where he took on various jobs, including driving auto parts, road construction, and enlisting in the United States Marine Corps reserves.
David's acting career took off when he was cast in the chorus of the Chicago musical "One Shining Moment," starring Megan Mullally, Kevin Anderson, and Alan Ruck. He later applied to the American Academy of Dramatic Arts and was accepted, which led him to move to New York City.
In the city, David struggled to find substantial work and turned to sobriety with the help of a friend. He eventually landed a role in John Guare's play "Six Degrees of Separation" and went on to work in various theater productions, including stints in East Harlem and as a carpenter and painter to make ends meet.
David's breakthrough came when he landed the recurring role of Steve in the hit TV show "Sex and the City," which he played for almost five years. During this time, he met Chrysti, an Army specialist, at a USO gala event and the two formed a deep connection.