Pressly dated her Jack and Jill co-star Simon Rex in 2000 and 2001. In a December 10, 2001 radio interview with Howard Stern, she said that Rex broke up with her on her birthday.[10]
In October 2006, she became engaged to her boyfriend of a year-and-a-half, DJ Eric Calvo (aka DJ Eric Cubiche), with whom she had been friends for nine years. Pressly gave birth on May 11, 2007 at 7:31 a.m. in Cedars-Sinai Medical Center to their first child, Dezi James Calvo.[11] In a February 2007 interview on The Tonight Show With Jay Leno, Pressly said she wants the child to be bilingual (English/Spanish) to reflect Calvo's Cuban heritage. The Emmy-nominated actress told People Magazine the name is part of a running joke, as Cuban-American Calvo does a Desi Arnaz impersonation, calling Pressly "Luuucy" when he comes home at night.[12]
Pressly said in a 2006 interview with Esquire magazine that she almost purchased a ticket for a flight on one of the planes that crashed into the World Trade Center on September 11, 2001, but decided not to take the flight because she felt it left too early in the morning