How to make time-loops more interesting.

I've got the main idea. I've got the character's name (Jamie) but I have no idea how to make this sitcom idea work (from a dream I had):

"Are you still reading Judy Blume, that is soooo 80's. What's in style is the Matrix, The Matrix!" Jamie said in his smarmiest tone to his sister. Coincidentally that day was the 4th of May- and that was when all his troubles really began…

Announcer: Ever since the 4th of May, Jamie was now cursed to go through a repeating time-loop on the fourth of every month

Question is: How to I make the time-loop curse more weird and more comedic? In the goofiest way possible. In my dream Jamie was this scarcastic smarmy teenage blonde hipster with technicolour 90's clothes.

edited 5th Feb '13 5:08:59 PM by sabrina_diamond

Question: When you say your character goes through a repeating timeloop on the fourth of every month do you mean that time progresses normally then suddenly on the fourth they repeat the day once or twice then go back to time progressing normally until the fourth of next month when the time loop happens gain?

Or do you mean that on the fourth of every month they get stuck in a time loop and have to find a way to break free of it before normal time progression can be restored? Also is the time loop just for that day or does it loop back to a specific time/date like the day he told his sister off for reading Judy Bloom novels or does it loop back to random days in past decades/centuries?

You culd have it so that on the fourth of every month he loops back to when Judy Bloom was writing the book his sister was reading but on a day when she suffered a spot of writers block. Every month he goes back to that same day but even though he remembers his past visits for Judy Bloom its like she only just met him and the day plays out differently each time (kinda like the movie fifty first dates but with a time loop instead of anterograde amnesia and no romance). Gradually he forms a weird friendship and respect for her and tries to help her with her writers block and feels sorry for teasing his sister about reading Judy Bloom.