Jack's First Date (S01E03)

Mr. Floppy encourages Jack to explore dating. During back-to-school night at Howe High, Jack, along with Jennifer, Ryan, and Tiffany, attempts to attract some female attention. To his surprise, he scores a date with Miss Taylor, Ryan's Civics teacher, who is the object of affection for many of the male teachers and students, as well as some female staff. Although Jennifer lends Jack her car for the date, her support is lacking. When he arrives to pick it up, he finds that Jennifer has taken it for a joyride with Maureen, leaving Jack to meet Miss Taylor three hours late, only for Ryan's friend, the paperboy, to end up going home with her.