Stern grew to be tall, standing 6 ft 5 in (1.96 m). On June 4, 1978, Stern married college sweetheart Alison Berns at Temple Ohabei Shalom in Brookline, Massachusetts. They have three daughters: Emily Beth (b. 1983), Deborah Jennifer (b. 1986) and Ashley Jade (b. 1993). A hallmark of Stern's humor was his claiming to be tempted by the strippers, porn stars and lesbians appearing on his show, but always insisted that he had to be faithful to his wife. In 1994, Stern ran for Governor of New York as a libertarian. The campaign was generally seen as a political stunt and Stern dropped out before the election after refusing to disclose his finances, a requirement by the State of New York. In October 1999, Stern announced that he and wife Alison decided to separate. They amicably divorced in 2001, ending in a settlement.

Stern began a period of single living on New York City's Upper West Side, dating dozens of women including Angie Everhart and Robin Givens. Desp