Continuity mistake: When Reuben and his client are playing racquetball, the client smashes against the wall and his tooth falls out. He shows the tooth to Reuben and the hole in in his teeth where it used to be, but in the next shot, Reuben's client smiles and all his teeth are in place.
Continuity mistake: When Sandy is dressed as Judas Iscariot, he is wearing a wig and a fake beard. He is clean shaven. The very next scene he has a three-day shadow, but only minutes have elapsed.
Visible crew/equipment: When Reuben is playing racquet ball with Leland van Lew, you can see the camera crew in the reflection of the glass wall. Also, the reflection of the lighting rig with a crew member standing beside it can be seen in Leland's glasses.
Continuity mistake: When Reuben and Sandy are talking in the street after the play disaster, and Sandy is telling Reuben about the fake E! True Hollywood Story, Reuben's tie keeps changing. In one shot, the tie has a dimple and is in a full windsor knot, and in other shots, the tie has no dimple and appears to be in a half-windsor knot.
Continuity mistake: When Reuben "accidentally" bumps into Polly at her apartment for the first time, he sees her crouching on the floor trying to find her keys in her purse. Next to her is a shopping bag with a loofah in it, whose handle keeps dramatically changing position in each shot.
Continuity mistake: When Reuben and Polly go to that Latin club to dance, after he's had salsa lessons, you see the guitarist pointing to encourage him. Now, he looks as if he's a left-handed guitar player, but a minute later you see him in the background playing right-handed. If you look for it, you can see that his guitar is a Gibson, and on the "lefty" scene the logo on the headstock is obviously reversed, which means the shot got mirrored in post-production.
Continuity mistake: For the arrival at St. Bart three different planes are used: The shadow on the ocean belongs to a single-propeller machine, the following close-up shows two engines and an antenna on top of the cockpit, and when the plane lands the antenna is gone and the engines are much smaller.
Continuity mistake: After Reuben's arrival in Los Angeles, where he is supposed to meet Leland van Lew, he sees him entering the service elevator. They go up to the rooftop together from where Leland does a base jump, using a parachute that he is wearing under his jacket. However, when we saw him at the ground floor there was nothing under his jacket: in the front the belt should have been partly visible, and also the bulge in the back wasn't there.
Continuity mistake: When Reuben and Sandy are playing basketball for the first time, Sandy's t-shirt is tucked under in one shot, and the next it is fine and untucked.
Other mistake: The scenes that are supposedly located in St. Bart's have Chinaman's Hat in the background, which is a distinctive Hawaiian landmark.
Continuity mistake: In the scene right after Reuben discovers Lisa cheating on him, Reuben begins to pack his truck to leave the island. The truck is facing the ocean as he loads the truck. However, a split second later he gets in the truck and the truck is facing away from the ocean, then when Reuben backs up, he backs up towards the ocean.