This movie bored me to tears and I was so happy I borrowed this from the Public Library. At least I could not be upset about spending money to view the DVD. The movie is about a dorky office guy named Stanley who wants to date the gorgeous new office worker(Denise Richards) named Diana. Every time he decides to make his move, he loses his confidence. A year passes before he finally manages to ask her out for a date, a causal date. Surprise, Surprise she agrees, but she feels the date will be a dud. The office forms a pool as to how far the date will go. Stan takes her to dinner, but while he is driving the car he hits a homeless guy named Phil. They take him to the hospital, and after that they can't seem to lose this guy. From here chaos ensues, with Phil pretty much following them the whole date. That's when I start to lose interest. Phil's character was annoying!!! His character was supposed to be like cupid or he was to help make things better during the date, but his character was so annoying, so irritating that the film lost any romantic comedy momentum. Everything he did was not funny and it's a miracle I even finished watching the film. My hand was itching to grab the remote to forward past Phil's annoying scenes. Ben Affleck has a supporting role in the film as Michael, and Matt Damon make a cameo about an 1 hour into the film that really was not needed in my opinion. If you want to be bored to sleep, then rent this movie. If you are looking for a good romantic comedy, do not watch this movie!!!