An shy writer has to go out on a date with a different man every month in order to write an article for her company’s ‘Man for Every Month’ blog.

Wingman rule number one: don’t fall for a client.

Struggling actor Wayne Wenders (Eric Mabius) is comically famous for starring in a low-budget commercial for Irritable Bowel Syndrome medication, a reputation he is hoping to change when he finally lands a starring role in a national root beer ad. But when the paycheck for his big break is delayed, Wayne looks for other options to pay his increasingly late rent and ends up interviewing for a gig teaching Shakespeare at the local high school. Principal Brenda Post (Stefanie Powers) hires Wayne for his natural theatrical talent and enthusiasm, but Wayne is soon surprising himself with his love of the job—and for fellow English teacher Amy (Virginia Williams), who is immediately impressed with Wayne’s passion and his idea to teach the students with an exciting film project. As Wayne’s understanding of teaching develops and his relationship with Amy evolves, he must ultimately decide if his dreams of stardom are really worth sacrificing everything for.