When Didi realizes that her irresponsible boy-friend isn't going to show up for her birthday, Annie O'Donnell uses a $100 off coupon and a virgin visa card with a $400 limit that she was saving for her honeymoon to treat Didi to a glamorous night at the Plaza Hotel. Meanwhile Roger and Elliot do some male bonding and discover that when it comes to women, they don't have anything in common.

When Didi's ex-husband shows up at her rent raising party, Annie, who didn't know he existed, feels betrayed by Didi and considers ending their friendship. Also at the party, Elliot, who is feeling rejected by his career-oriented wife, flirts with another woman, and Roger complains that he is being smothered by his lastest conquest, a woman he met only hours before.

When the new boss disguises himself as a job applicant to spy on Annie, Roger and Elliot. The three fail the test miserably and worry that their jobs are in jeopardy when Mr. Barbour reveals his true identity. Mr. Barbour pushes the three to the edge as he institutes strict new office rules, but Annie puts her job on the line when Barbour tells her to stop placing clients like Didi, who quits just about every job after a day. Meanwhile, Roger threatens to quit when Barbour insists that all employees wear a polyester uniform.