Trey wins a date with Sylvia at the paper's celebrity auction, but his evening is interrupted by amorous Old Man Russell (Ed Asner),who is intent on taking Sylvia home with him. Angelica Bridges has a cameo.
Sylvia goes to pick up her first paycheck, only to find that she can't get it until she gets a physical examination---from a gynecologist (Tony Carreiro). Nurse: Mary Pat Gleason. Joplin: Julie Benz. Ron: Willie Garson.
"Sylvia" (Anthony Tyler Quinn) hatches a scheme to get Jack his job back, but Old Man Russell's demands make him go bananas. Ron: Willie Garson. Old Man Russell: Ed Asner. Melissa: Lisa Waltz. Trey: Patrick Y. Malone.
When Jack learns that the paper's owner (Ed Asner), is coming, he tries to get his job back, but the man is more interested in "Sylvia." Ron: Willie Garson. Trey: Patrick Y. Malone. Melissa: Lisa Waltz.
Jack is fired by his New York newspaper and rebounds by being rehired as their advice-to-the-lovelorn columnist---Sylvia Coco. Ron: Willie Garson. Trey Anderson: Patrick Y. Malone. Melissa: Lisa Waltz.