Everhart was briefly engaged to Sylvester Stallone in 1995, married to Ashley Hamilton from December 1996 until March 1997, and has been rumored to be involved with Prince Albert of Monaco. She briefly dated Howard Stern after his divorce from his wife and before he became engaged to his current wife, Beth Ostrosky. Stern has admitted to it and openly discussed having dated and slept with her. Stern only went public about his tryst with Everhart because she went public with it first, calling Stern the "best sex she's ever had" in an interview with FHM magazine. She met the Duke of York in 2002 and by 2006 they were in a relationship. She has also dated Orlando Jones.

It was announced on July 30, 2007 that Everhart was engaged to actor Joe Pesci, but on April 25, 2008, the couple announced their separation