Skeeter Bronson (Adam Sandler) does repairs on hotels and feels a bit unlucky. One day, his sister Wendy (Courteney Cox) wants him to babysit for her because she’s looking for work. She has her pal Jill (Keri Russell) watching the kids during the day. During each night, Skeeter tells the kids, Bobbi (Laura Ann Kiesling) and Patrick (Jonathan Morgan Heit), a sad story about his frustrating and unfulfilling life, but they add things to it to make it a happier story. After that, the story elements begin to happen for real during the day. Skeeter realizes he just might be able to turn his life around if the kids keep coming up with positive ideas.