Man is hunted for a game

The plot is about a guy, who goes from being paranoid that people are after him, into being outright harassed. He meets a woman who he confides in, but she is in on it as well. He goes to her apartment and finds her books are fake cutouts and her furniture has all the tags still on it. He is then shot at by people with submachine guns, and transitions into being kidnapped, put into a box, and dumped in Mexico. When he stumbles back to the United States, I think he parachutes through glass into a banquet hall and finds a party going on where his friends congratulate him and give him a T-shirt that says something like “I was kidnapped and dumped in Mexico and all I got was this stupid shirt.” So his rich friends did some elaborate prank hiring a company to do this to him. It ends with the protagonist going outside to ask out the woman who was in on the whole plan.
I believe the era for this movie is the 2000’s.
If anyone knows what this is I’ll raise a glass to them.