He has even devised elaborate but mostly unsuccessful schemes to trick the Waitress into going out with him including:. Instead she sleeps with Frank Dennis' father and Charlie's roommate. Charlie calls the franchise owner who fires Dee, Dennis and Charlie. She even has a restraining order against him. After sleeping together, the Waitress admits the experience was better than expected and becomes dependent on Charlie as a result of carrying his child. They devise an elaborate plot to sleep together in Charlie's apartment. The Waitress drops Charlie and he goes back to drinking and ruins the basketball game of the kids the gang were mentoring as part of their community service. He also fires the Waitress for being dumb enough to hire them in the first place.