Oh my christ yes. This was always near the top of my "worst movies ever that flew under the radar".
The script was written by a social cripple's imagination of a tech bro's social life.
Josh Hartnet's comedic skill and performance never deviates from an expression that looks like someone who has to take a diarrhea shit right at the same time they learn that their dog died. He sweats and mopes his way through the entire movie. COMEDY!
No seriously, the ENTIRE MOVIE is Hartnet sweating with constipated sad face.
On the last night, he decides to wait for Shannyn Sossamon to come in and ties himself to the bed. His ex-girlfriend rapes him while he's asleep. This is treated as him cheating and is never called rape.