The movie poster for this film is a take on a famous "Rolling Stone" magazine cover of Yoko Ono and John Lennon in which John was completely naked.
Jennifer Love Hewitt was offered the role of "Cam Wexler", but turned it down because of scheduling conflicts. The role then went to Jessica Alba.
The original script was titled "The Warm-Up Guy".
The quartet that sings to Cam is Antique Gold, the 2006 Seniors Champions of the Barbershop Harmony Society.
In the movie, the building where Chuck and Stu work at is named the Seltaeb building. Backwards, "seltaeb" is "beatles". Seltaeb was also the name of the corporation which in 1964, oversaw product licensing arrangements for The Beatles.
Originally, New Line Cinema was set to distribute, but they gave the film to Lionsgate shortly before production. A similar situation occurred when the studio gave distribution rights for Alpha Dog (2006) to Universal Pictures, but that case was related to controversy over real-life events.
The Perfectmatch.com ad for Charlie on Reba's computer screen says this: "Charlie Logan, DDS, a local dentist is fast becoming a legend. Women claim that he's a lucky charm because everyone he shakes the sheets with finds her soul mate in the next guy she dates. Lucky for you, he's not bad on the eyes either. Dr. Logan goes by Charlie to his friends. Was known as Chuck in high school and sometimes uses the name Charles for his work. He frequents the coffee shop on Third and Main Street (in the lobby of the building that houses his practice). He was also spotted at a jazz club downtown last Thursday, where he went to see delta blues guitarist Josh Stolberg, who next plays there on 16th of the month. We are currently trying to find a home address for him (please check back soon)."
Charlie's car is a 1957 Ford Thunderbird.
Cam's car is a 2006 Toyota Prius II with an "I <3 PENGUINS" bumper sticker.
The song playing during the phone call montage is 'I Love it When You Call' by The Feeling. The lyrics of the song continue "but you never call at all" but this doesn't fit with the theme of the montage when Cam and Chuck are constantly on the phone. Therefore, some of the lyrics are blanked out of the soundtrack, leaving several gaps.