Denise Quiñones was originally cast as Lara. She dropped out two days before filming started. Marika Dominczyk, who was the original first choice but had passed months earlier due to a scheduling conflict, was now available and immediately stepped into the role.
During the scene where Dan (Geoff Stults) is trying to convince his fiancé to allow him to go to Salem, Drew mentions, while waiting in the car, that this will be about as good as a "Friends" spin-off. Geoff Stults played a role on Joey (2004), a spin-off based on a character in "Friends".
The commercial for "De Nils Diamonds" is a reference to Nils Parker, who co-wrote the screenplay and produced the film. There was also a huge debate regarding the diamond trade on Tucker Max's online forum, with many of the members agreeing with Drew's scripted opinion in this scene.
The movie poster showing Tucker with a blonde woman next to him, with a "your face here" graphic over her face, framed on the top and bottom by black areas with text in them, is nearly identical to the cover of the book the movie is based on.