Unhappily Ever After (1995)

Season 1: Episode 3

Mr. Floppy thinks that Jack should start dating. While Jack, Jennifer, Ryan, and Tiffany go to Howe High's back to school night, Jack tries to send out ""the vibe"" to the women there. Amazingly he gets a date with Miss Taylor (Ryan's Civics Teacher), whom all the male teachers and students, and half the female teachers are after. Jennifer agrees to lend Jack the car for the date, but is less than supportive of him. When Jack comes to pick up the car, Jennifer and the car aren't there-- she and Maureen have taken it to the otherside of the block. Jack ends up meeting Miss Taylor 3 hours late, and Ryan's friend the paperboy ends up going home with her.