Continuity mistake: When Jill spanks Michael with the special "scarlet letter" paddle, she stands and swings it like a baseball bat. This would've left a sideways A on his butt. Later, you see Michael walking away from the camera, nude. To leave the A at the angle shown in the second scene, Jill would've had to rest on her knees and swing the paddle like an axe.
Continuity mistake: The film goes to such lengths to show that Michael has NONE of his possessions left, especially all his clothes, after his stuff is taken by the casino owner's goons. However, whenever Michael goes out in public, he's dressed well again. But later, when he's shown at home, he's once again dressed in rags.
Continuity mistake: When Kyle and Natalie are walking on the beach hand-in-hand, and Michael is climbing the cliff to spy on them, watch closely as it shows Michael sliding down the cliff. It's clearly a stunt-double, as the body is short and round, while Jerry O'Connell, who plays Michael, is tall and thin.