Wolf was born in Boston, Massachusetts. His mother, Susan Enowitch (née Levy), is a drug abuse counselor, and his father, Steven Wolf, is a health care executive.Wolf was raised in Reform Judaism. He grew up in West Orange, New Jersey and graduated in 1986, from West Orange High School. He attended The George Washington University and received a Bachelor of Arts degree in finance. He also became a Brother of the Alpha Epsilon Pi Fraternity. His cousin is comedian and Chelsea Lately regular Josh Wolf.

Wolf is known for his role as Bailey Salinger on Party of Five. On both Everwood and the short-lived The Nine, he portrayed a doctor; his own maternal grandfather was an anesthesiologist. He also made guest appearances as himself on Action and Kids Inc. His sole Broadway theatre credit to date is Side Man.

In 2002, Wolf began dating Kelley Limp, an alumna of MTV's The Real World: New Orleans, after meeting through a mutual friend in New York City. They married on May 29, 2004, and planned to make their home in Santa Monica, California.Their son, Jackson Kayse, was born on March 22, 2009.

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