Benny is too shy to ask a girl out on a date, so to help him out, Alan asks Karen Frankel, a classmate Benny has always liked, to a couples-only party, and asks Katie to go with Benny, then they will ""trade"" later on. But Benny develops a crush on Katie and Alan learns that Karen has had a crush on him for years. Meanwhile Sophie and Phyllis help organize a rummage sale which honors the fallen son of a neighbor in aid of a veterans' hospital, while George invests in one of the new Polaroid cameras.

Benny tells Alan that Katie is now his girlfriend and they can't be friends any longer; meanwhile, Karen Frankel further misunderstands her relationship with Alan, and, during preparations for the rummage sale, Aunt Sylvia and Sid seem to be hitting it off.