Plot hole: When Carlos (Bill Maher) is explaining to Michael what was a valid roll he says that the redhead rubbed the dice on her chest for good luck and threw them. However she immediately threw the dice when Michael handed them to her. She only rubbed them on her chest and gave them back to Michael on a prior roll.
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.
Other mistake: When Kyle and Natalie are in the bedroom together and she reaches in the drawer to grab the lotion for him. You can planly see that the logo for the Jergens bottle is censored and the logo is blurred out.
Revealing mistake: When Michael is gambling his money away, the first time we see him throw the dice on the craps table, the dice head off camera to the top and upper right corners. When the dice "bounce back" they come from the upper left side of the screen together as if thrown from right off camera.
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 Michael is with the librarian, and she goes to put on the purple knee high boots, you see her take them out of the chest and put one on, then there's a quick cutaway and both boots are on when she stands.
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.
Continuity mistake: When Michael is climbing on the rocks, he turns his head and sees them walking on the beach, and his hair is blowing. The next shot shows his hair lying flat with no wind at all.