There Once Was a Girl from Nantucket

Plot:

Brian asks a girl out and she agrees on the condition that he find someone for her friend Cindy. And he volunteers Joe. Joe initially refuses but Brian guilts him into it. Later he learns that Cindy is very "popular", which makes him reconsider, but then Helen guilts him. And at their date one of her exes shows up and when he treats her crudely Joe stands up for her.